A method for preparing a quinone compound

Abstract

This invention discloses a method for preparing quinone compounds. The method comprises the following steps: in the presence of a base, a compound as shown in Formula II and a compound as shown in Formula III undergo a condensation reaction to obtain a quinone compound as shown in Formula I; wherein the base is more basic than sodium phenolate. This method is simple to operate and suitable for industrial production.

Description

[0001] This application claims priority to Chinese patent application 202010466652.X, filed on May 28, 2020. The entire contents of the aforementioned Chinese patent application are incorporated herein by reference. Technical Field

[0002] This invention relates to a method for preparing quinone compounds. Background Technology

[0003] Benzoquinones possess unique structural and functional characteristics, are widely distributed in nature, and play important roles. Compounds containing quinone functional groups, such as coenzyme Q10, vitamin K, and plastoquinones, are electron transfer carriers in biochemical processes like respiration and photosynthesis in eukaryotes. Studies have shown that coenzyme Q10 and vitamin K are essential vitamins for the human body, playing a positive role in organs and tissues such as the heart and bones. However, the dietary sources of these vitamins are limited; therefore, chemical synthesis is an important source, and successful synthetic methods have enormous market potential.

[0004] Classic methods for synthesizing quinone compounds generally start with raw materials such as phenol and aryl ethers, and perform side chain modification through functionalization reactions such as Lewis acid and metal-catalyzed coupling. Then, the aryl ethers are deprotected and oxidized. These reactions use a lot of catalysts, protecting group reagents and oxidants, and the process is lengthy and inefficient.

[0005] Therefore, it is of great significance to develop new methods for the synthesis of quinone compounds that are simple, efficient, and widely applicable. Summary of the Invention

[0006] The technical problem this invention aims to solve is that existing methods for preparing quinone compounds are relatively limited. Therefore, this invention provides a method for preparing quinone compounds. This method is simple to operate and suitable for industrial production.

[0007] This invention provides a method for preparing a quinone compound as shown in Formula I, comprising the following steps: in the presence of a base, performing a condensation reaction between a compound as shown in Formula II and a compound as shown in Formula III to obtain a quinone compound as shown in Formula I; wherein the base is more basic than sodium phenolate.

[0008]

[0009] Among them, R 1 Hydrogen, C1 to C 10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0010] R 2 Hydrogen, C1 to C 10 Alkyl groups, C2-C10 alkenyl or C1-C 10 alkoxy groups;

[0011] R 3 Hydrogen, C1 to C 10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0012] Or, R 2 R 3 Together with the carbon atoms attached to it, they form C6 to C6 carbon atoms. 10 aryl group, C6-C6 substituted with one or more hydroxyl groups 10 The aryl group, or a 5- to 10-membered heteroaryl group; wherein the heteroatom in the heteroaryl group is selected from one or more of N, O and S, and the number of heteroatoms is 1, 2 or 3;

[0013] R 4 It is O;

[0014] R 5 It is O;

[0015] R 6 C3~C 100 alkenyl group, by one or more R 6-1 Replacement of C3~C 100 alkenyl, or, C3~C 10 Cycloalkenyl groups;

[0016] R 6-1 Independently C6~C 10 The aryl group, or a 5- to 10-membered heteroaryl group; wherein the heteroatom in the heteroaryl group is selected from one or more of N, O and S, and the number of heteroatoms is 1, 2 or 3;

[0017] X is a halogen.

[0018] In one embodiment, certain technical features of the above preparation method are described below, and the remaining technical features are as described in any of the above or following embodiments (hereinafter referred to as "in one embodiment"): R 1 Hydrogen, C1 to C 10 Alkyl or C1-C 10 alkoxy groups.

[0019] In one particular scheme, R 2 Hydrogen, C1 to C 10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0020] R 3 Hydrogen, C1 to C10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0021] Or, R 2 R 3 Together with the carbon atoms attached to it, they form C6 to C6 carbon atoms. 10 aryl group, or C6-C6 substituted with one or more hydroxyl groups. 10 Aryl groups.

[0022] In one particular scheme, R 2 Hydrogen, C1 to C 10 Alkyl or C1-C 10 alkoxy groups;

[0023] R 3 Hydrogen, C1 to C 10 Alkyl or C1-C 10 alkoxy groups;

[0024] Or, R 2 R 3 Together with the carbon atoms attached to it, they form C6 to C6 carbon atoms. 10 aryl group, or C6-C6 substituted with one or more hydroxyl groups. 10 Aryl groups.

[0025] In one particular scheme, R 2 It is hydrogen, a C1-C4 alkyl group, or a C1-C4 alkoxy group;

[0026] R 3 It is hydrogen, a C1-C4 alkyl group, or a C1-C4 alkoxy group;

[0027] Or, R 2 R 3 Together with the carbon atom attached thereto, they form a phenyl group, or a phenyl group substituted with one or more hydroxyl groups.

[0028] In one particular scheme, R 6 C3~C 100 The alkenyl group.

[0029] In one particular scheme, R 6 Chloroplasts n is 0 to 9 (e.g., 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9).

[0030] In one particular scheme, R 6-1 Independently C6~C 10 Aryl groups.

[0031] In one particular scheme, R1 R 2 and R 3 At most one of them is hydrogen.

[0032] In one particular scheme, R 1 R 2 and R 3 One of them is hydrogen.

[0033] In one particular scheme, R 1 For hydrogen, R 2 and R 3 It is not hydrogen.

[0034] In one particular scheme, R 2 For hydrogen, R 1 and R 3 It is not hydrogen.

[0035] In one particular scheme, R 3 For hydrogen, R 1 and R 2 It is not hydrogen.

[0036] In one particular scheme, R 1 R 2 and R 3 None of them are hydrogen.

[0037] In one particular scheme, R 1 R 2 and R 3 Two of them are hydrogen.

[0038] In one particular scheme, R 1 R 2 and R 3 Both are hydrogen.

[0039] In one particular scheme, R 1 Hydrogen, C1 to C 10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0040] R 2 Hydrogen, C1 to C 10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0041] R 3 Hydrogen, C1 to C 10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0042] Or, R 2R 3 Together with the carbon atoms attached to it, they form C6 to C6 carbon atoms. 10 aryl group, or C6-C6 substituted with one or more hydroxyl groups. 10 aryl;

[0043] R 4 It is O;

[0044] R 5 It is O;

[0045] R 6 C3~C 100 alkenyl group, by one or more R 6-1 Replacement of C3~C 100 alkenyl, or, C3~C 10 Cycloalkenyl groups;

[0046] R 6-1 Independently C6~C 10 aryl;

[0047] X is a halogen.

[0048] In one particular scheme, R 1 Hydrogen, C1 to C 10 Alkyl or C1-C 10 alkoxy groups;

[0049] R 2 Hydrogen, C1 to C 10 Alkyl or C1-C 10 alkoxy groups;

[0050] R 3 Hydrogen, C1 to C 10 Alkyl or C1-C 10 alkoxy groups;

[0051] Or, R 2 R 3 Together with the carbon atoms attached to it, they form C6 to C6 carbon atoms. 10 aryl group, or C6-C6 substituted with one or more hydroxyl groups. 10 aryl;

[0052] R 4 It is O;

[0053] R 5 It is O;

[0054] R 6 C3~C 100 alkenyl groups;

[0055] X is a halogen.

[0056] In one particular scheme, R1 It is hydrogen, a C1-C4 alkyl group, or a C1-C4 alkoxy group;

[0057] R 2 It is hydrogen, a C1-C4 alkyl group, or a C1-C4 alkoxy group;

[0058] R 3 It is hydrogen, a C1-C4 alkyl group, or a C1-C4 alkoxy group;

[0059] Or, R 2 R 3 Together with the carbon atom attached thereto, they form a phenyl group, or a phenyl group substituted with one or more hydroxyl groups;

[0060] R 4 It is O;

[0061] R 5 It is O;

[0062] R 6 Chloroplasts n is 0 to 9 (e.g., 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9);

[0063] X is a halogen.

[0064] In one embodiment, the compound represented by Formula II can be 1,4-benzoquinone, 2-methyl-1,4-benzoquinone, 2,3-dimethyl-1,4-benzoquinone, 2,3,5-trimethyl-1,4-benzoquinone, 2,3-dimethoxy-5-methyl-1,4-benzoquinone, 2-methyl-1,4-naphthoquinone, or 5-hydroxy-1,4-naphthoquinone;

[0065] R 6 3-Methyl-2-buten-1-yl (all-E)-3,7-dimethyl-2,6-octadien-1-yl (all-E)-3,7,11-trimethyl-2,6,10-dodecanetrien-1-yl Chloroplasts (all-E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecathateten-1-yl (all-E)-3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octadecahepathene-1-yl (all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexadecanononen-1-yl Or (all-E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetradecenoen-1-yl

[0066] In one embodiment, the compound represented by Formula II can be 2,3-dimethoxy-5-methyl-1,4-benzoquinone; R 6 for n can be 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0067] In one embodiment, the compound represented by Formula II can be 2,3-dimethoxy-5-methyl-1,4-benzoquinone; R 6 for n is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

[0068] The condensation reaction may have the following reaction parameters: the condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or o-dichlorobenzene, and the molar volume ratio of the compound represented by Formula II to the chlorobenzene or o-dichlorobenzene is 0.1 mol / L to 0.2 mol / L; the base is sodium hydride and... Sodium salt, R x for For tert-butyl, The molar ratio of the base to the compound shown in Formula II is (2–2.5):1; the condensation reaction is still underway. The above is carried out in the presence of the present, The molar ratio of the compound shown in Formula II to the compound shown in Formula III is (0.05–0.10):1; the molar ratio of the compound shown in Formula III to the compound shown in Formula II is (0.2–1.70):1; the temperature of the condensation reaction is 70°C–80°C.

[0069] In one embodiment, the compound represented by Formula II can be 2,3-dimethoxy-5-methyl-1,4-benzoquinone; R 6 for n is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

[0070] The condensation reaction may have the following reaction parameters: the condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or o-dichlorobenzene, and the molar volume ratio of the compound represented by Formula II to the chlorobenzene or o-dichlorobenzene is 0.1 mol / L to 0.2 mol / L; the base is sodium hydride and... R x for For tert-butyl, The molar ratio of the base to the compound shown in Formula II is (2-2.5):1. The molar ratio of the compound to that shown in Formula II is (0.03–0.3):1; the condensation reaction is still ongoing. The above is carried out in the presence of the present, The molar ratio of the compound shown in Formula II to the compound shown in Formula III is (0.05–0.10):1; the molar ratio of the compound shown in Formula III to the compound shown in Formula II is (0.2–1.70):1; the temperature of the condensation reaction is 70°C–80°C.

[0071] In one embodiment, the compound shown in Formula II can be 2-methyl-1,4-naphthoquinone; R 6 for n can be 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0072] In one embodiment, the compound shown in Formula II can be 2-methyl-1,4-naphthoquinone; R 6 for n is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

[0073] The condensation reaction may have the following reaction parameters: the condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or o-dichlorobenzene, and the molar volume ratio of the compound represented by Formula II to the chlorobenzene or o-dichlorobenzene is 0.1 mol / L to 0.2 mol / L; the base is sodium hydride and... Sodium salt, R x for For tert-butyl, The molar ratio of the base to the compound shown in Formula II is (2–2.5):1; the condensation reaction is still underway. The above is carried out in the presence of the present, The molar ratio of the compound shown in Formula II to the compound shown in Formula III is (0.05–0.10):1; the molar ratio of the compound shown in Formula III to the compound shown in Formula II is (0.2–1.70):1; the temperature of the condensation reaction is 70°C–80°C.

[0074] In one embodiment, the compound shown in Formula II can be 2-methyl-1,4-naphthoquinone; R 6 for n is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

[0075] The condensation reaction may have the following reaction parameters: the condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or o-dichlorobenzene, and the molar volume ratio of the compound represented by Formula II to the chlorobenzene or o-dichlorobenzene is 0.1 mol / L to 0.2 mol / L; the base is sodium hydride and... R x for For tert-butyl, The molar ratio of the base to the compound shown in Formula II is (2-2.5):1. The molar ratio of the compound to that shown in Formula II is (0.03–0.3):1; the condensation reaction is still ongoing. The above is carried out in the presence of the present, The molar ratio of the compound shown in Formula II to the compound shown in Formula III is (0.05–0.10):1; the molar ratio of the compound shown in Formula III to the compound shown in Formula II is (0.2–1.70):1; the temperature of the condensation reaction is 70°C–80°C.

[0076] In a certain scheme, when R 1 C1~C 10 When alkyl groups are present, the C1-C1 group is... 10 The alkyl group can be a C1 to C4 alkyl group, or it can be a methyl group.

[0077] In a certain scheme, when R 1 For C2~C 10 When the alkenyl group is present, the C2-C 10 The alkenyl group can be a C2 to C5 alkenyl group, or it can be a 3-methyl-2-buten-1-yl group.

[0078] In a certain scheme, when R 1 C1~C 10 When the alkoxy group is present, the C1-C1... 10 The alkoxy group can be a C1 to C4 alkoxy group, or it can be a methoxy group.

[0079] In a certain scheme, when R 2 C1~C 10 When alkyl groups are present, the C1-C1 group is... 10 The alkyl group can be a C1 to C4 alkyl group, or it can be a methyl group.

[0080] In a certain scheme, when R 2 For C2~C 10 When the alkenyl group is present, the C2-C 10 The alkenyl group can be a C2 to C5 alkenyl group, or it can be a 3-methyl-2-buten-1-yl group.

[0081] In a certain scheme, when R 2 C1~C 10 When the alkoxy group is present, the C1-C1... 10 The alkoxy group can be a C1 to C4 alkoxy group, or it can be a methoxy group.

[0082] In a certain scheme, when R 3 C1~C 10 When alkyl groups are present, the C1-C1 group is... 10 The alkyl group can be a C1 to C4 alkyl group, or it can be a methyl group.

[0083] In a certain scheme, when R 3 For C2~C 10 When the alkenyl group is present, the C2-C 10 The alkenyl group can be a C2 to C5 alkenyl group, or it can be a 3-methyl-2-buten-1-yl group.

[0084] In a certain scheme, when R 3 C1~C 10 When the alkoxy group is present, the C1-C1... 10 The alkoxy group can be a C1 to C4 alkoxy group, or it can be a methoxy group.

[0085] In a certain scheme, when R 2 R 3 Together with the carbon atoms attached to it, they form C6 to C6 carbon atoms. 10 When the aryl group is present, the C6-C 10 The aryl group can be phenyl.

[0086] In a certain scheme, when R 2 R 3 Together with the carbon atom attached thereto, they form C6-C atoms that are substituted with one or more hydroxyl groups. 10 When the aryl group is present, the C6-C 10 The aryl group can be phenyl.

[0087] In one embodiment, the compound represented by Formula II may be 1,4-benzoquinone, 2-methyl-1,4-benzoquinone, 2-methoxy-1,4-benzoquinone, 2,3-dimethyl-1,4-benzoquinone, 2,6-dimethyl-1,4-benzoquinone, 2,6-dimethyl-3-(3-methyl-2-buten-1-yl)-1,4-benzoquinone, 2,3,5-trimethyl-1,4-benzoquinone, 2,3-dimethoxy-5-methyl-1,4-benzoquinone, 2-methyl-1,4-naphthoquinone, or 5-hydroxy-1,4-naphthoquinone.

[0088] In a certain scheme, when R6 C3~C 100 When the X is an alkenyl group, the β-position and γ-position of X can both be double bonds.

[0089] In a certain scheme, when R 6 C3~C 100 When the alkenyl group is present, the C3-C 100 The alkenyl group can contain 1 to 15 double bonds, and can also contain 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 double bonds.

[0090] In a certain scheme, when R 6 C3~C 100 When the alkenyl group is present, the C3-C 100 The alkenyl group can be C5 to C6. 100 The terpene group can also be used for " n is 0 to 19 (e.g., 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 or 19, or 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9)).

[0091] In a certain scheme, when R 6 C3~C 100 When the alkenyl group is present, the C3-C 100 The alkenyl group can be C3 to C4. 50 The alkenyl group can also be C3, C4, C5, C6, C7, C8, C9 ... 10 alkenyl, C 15 alkenyl, C 20 alkenyl, C 30 alkenyl, C 40 alkenyl, C 45 alkenyl or C 50 The alkenyl group can also be allyl, 2-buten-1-yl 3-Methyl-2-buten-1-yl 2-Hexen-1-yl (all-E)-3,7-dimethyl-2,6-octadien-1-yl (all-E)-3,7,11-trimethyl-2,6,10-dodecanetrien-1-yl Chloroplasts (all-E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecathatetraen-1-yl (all-E)-3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octadecahepathene-1-yl (all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexadecanononen-1-yl Or (all-E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetradecenoen-1-yl

[0092] In a certain scheme, when R 6 For one or more R 6-1 Replacement of C3~C 100 When the X is an alkenyl group, the β-position and γ-position of X can both be double bonds.

[0093] In a certain scheme, when R 6 For one or more R 6-1 Replacement of C3~C 100 When the alkenyl group is present, the C3-C 100 The alkenyl group can contain 1 to 15 double bonds, and can also contain 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 double bonds.

[0094] In a certain scheme, when R 6 For one or more R 6-1 Replacement of C3~C 100 When the alkenyl group is present, the C3-C 100 The alkenyl group can be C5 to C6. 100 The terpene group can also be used for " n is 0 to 19 (e.g., 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 or 19, or 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9)).

[0095] In a certain scheme, when R 6 For one or more R 6-1 Replacement of C3~C 100 When the alkenyl group is present, the C3-C 100 The alkenyl group can be C3 to C4. 50 The alkenyl group can also be C3, C4, C5, C6, C7, C8, C9 ... 10 alkenyl, C 15 alkenyl, C 20 alkenyl, C 30 alkenyl, C 40 alkenyl, C 45alkenyl or C 50 The alkenyl group can also be allyl, 2-buten-1-yl 3-Methyl-2-buten-1-yl 2-Hexen-1-yl (all-E)-3,7-dimethyl-2,6-octadien-1-yl (all-E)-3,7,11-trimethyl-2,6,10-dodecanetrien-1-yl Chloroplasts (all-E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecathateten-1-yl (all-E)-3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octadecahepathene-1-yl (all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexadecanononen-1-yl Or (all-E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetradecenoen-1-yl

[0096] In a certain scheme, when R 6 For multiple R 6-1 Replacement of C3~C 100 When the alkenyl group is present, the plurality of groups can be two or three.

[0097] In a certain scheme, when R 6-1 Independently C6~C 10 When the aryl group is present, the C6-C 10 The aryl group can be phenyl.

[0098] In a certain scheme, when R 6 For being an R 6-1 Replacement of C3~C 100 When the alkenyl group is present, it is subjected to an R 6-1 Replacement of C3~C 100 The alkenyl group can be replaced by an R 6-1 Replacement of C3~C 50 The alkenyl group can also be 3-phenyl-2-propen-1-yl.

[0099] In a certain scheme, when R 6 C3~C 10 When the cycloalkenyl group is present, the β-position and γ-position of X can both be double bonds.

[0100] In a certain scheme, when R 6 C3~C 10 When the cycloalkenyl group is present, the C3-C 10 The cycloalkenyl group can contain 1 to 5 double bonds, and can also contain 1, 2, 3, 4 or 5 double bonds.

[0101] In a certain scheme, when R 6 C3~C 10 When the cycloalkenyl group is present, the C3-C 10 The cycloalkenyl group can be a C3-C6 cycloalkenyl group, or it can be a 2-cyclohexen-1-yl group.

[0102] In one embodiment, when X is a halogen, the halogen can be chlorine, bromine, or iodine, or it can be chlorine or bromine.

[0103] In one embodiment, the compound represented by Formula I may have any of the following structures:

[0104]

[0105]

[0106] In one embodiment, the condensation reaction can also be carried out in the presence of a protective gas.

[0107] In one embodiment, the protective gas can be an inert gas or nitrogen, or nitrogen.

[0108] In one embodiment, the condensation reaction can be carried out in an organic solvent or under solvent-free conditions.

[0109] In one embodiment, when the condensation reaction can be carried out in an organic solvent, "the base is more basic than sodium phenolate" means that in the organic solvent, the base is more basic than sodium phenolate.

[0110] In one embodiment, when the condensation reaction can be carried out in an organic solvent, the organic solvent is one that is conventionally used in this type of condensation reaction in the art and can dissolve other materials.

[0111] In one embodiment, the organic solvent may be a nonpolar organic solvent, or a halogenated hydrocarbon solvent and / or a hydrocarbon solvent.

[0112] In one embodiment, the halogenated hydrocarbon solvent may be a halogenated alkane solvent and / or a halogenated aromatic hydrocarbon solvent.

[0113] In one embodiment, the haloalkane solvent may be dichloromethane and / or 1,2-dichloroethane.

[0114] In one embodiment, the halogenated aromatic hydrocarbon solvent may be one or more of fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, trifluorotoluene, o-dichlorobenzene, m-dichlorobenzene, and p-dichlorobenzene, and may also be chlorobenzene or o-dichlorobenzene.

[0115] In one embodiment, the hydrocarbon solvent may be an alkane solvent and / or an aromatic hydrocarbon solvent.

[0116] In one embodiment, the alkane solvent may be mineral oil.

[0117] In one embodiment, the aromatic hydrocarbon solvent may be one or more of benzene, toluene, o-xylene, p-xylene, m-xylene, and mesitylene, or toluene.

[0118] In one embodiment, the amount of organic solvent used is determined by its ability to dissolve other materials.

[0119] In one embodiment, when the condensation reaction can be carried out in an organic solvent, the molar volume ratio of the compound as shown in Formula II to the organic solvent can be 0.1 mol / L to 0.3 mol / L, or 0.1 mol / L to 0.2 mol / L.

[0120] In one embodiment, the anion of the base may be a hydride anion, hydroxide ion, amino anion, carbonate ion, phosphate ion, or...

[0121] R x C1~C 15 Alkyl groups, C3-C 10 cycloalkyl, or, by one or more R x-1 Substituted C1–C5 alkyl groups; R x-1 Independently hydroxyl, or C3-C3 substituted with one or more C1-C3 alkyl groups. 10 Cycloalkenyl groups.

[0122] In one embodiment, the anion of the base may be hydroxide, carbonate, or... R x C1~C 15 Alkyl groups.

[0123] In one of the solutions, Inside, and The bonded carbon atoms are tertiary carbon atoms.

[0124] In a certain scheme, when R x C1~C 15When alkyl groups are present, the C1-C1 group is... 15 The alkyl group can be methyl, ethyl, isopropyl, R x-2 C1~C 12 Alkyl groups.

[0125] In a certain scheme, when C1~C 15 The alkyl group is At that time, the R x-2 It can be C1 to C 12 Straight-chain alkyl groups.

[0126] In a certain scheme, when C1~C 15 The alkyl group is At that time, the R x-2 It can be a straight-chain alkyl group from C1 to C7.

[0127] In a certain scheme, when C1~C 15 The alkyl group is At that time, the It can be tert-butyl,

[0128] In a certain scheme, when R x C3~C 10 When cycloalkyl, the C3-C 10 The cycloalkyl group can be a bridged ring C5-C6. 10 Cycloalkyl groups, and can also be adamantyl groups (e.g. ).

[0129] In a certain scheme, when R x For one or more R x-1 When the substituted C1 to C5 alkyl groups are used, the plurality of alkyl groups may be 2, 3 or 4.

[0130] In a certain scheme, when R x-1 Independently refers to C3-C4 alkyl groups substituted with one or more C1-C3 alkyl groups. 10 When the cycloalkenyl group is used, the C1-C3 alkyl group can be methyl.

[0131] In a certain scheme, when R x-1 Independently refers to C3-C4 alkyl groups substituted with one or more C1-C3 alkyl groups. 10 When the cycloalkenyl group is present, the C3-C 10 The cycloalkenyl group can be a monocyclic C3-C6 cycloalkenyl group or a cyclohexenyl group.

[0132] In a certain scheme, when R x-1 Independently refers to C3-C4 alkyl groups substituted with one or more C1-C3 alkyl groups.10 When the cycloalkenyl group is substituted with one or more C1-C3 alkyl groups, the C3-C3 group is... 10 The cycloalkenyl group can be

[0133] In a certain scheme, when R x For one or more R x-1 When a C1-C5 alkyl group is substituted, the C1-C5 alkyl group may be n-propyl, isopropyl, or neopentyl.

[0134] In one embodiment, the cation of the base may be an alkali metal ion or an alkaline earth metal ion.

[0135] In one embodiment, the alkali metal ion may be lithium ion, sodium ion, or potassium ion.

[0136] In one embodiment, the alkaline earth metal ions may be magnesium ions or calcium ions.

[0137] In one embodiment, the alkali may be selected from one or more (e.g., two, three, four, or five) of the following group: alkali metal hydrides, alkali metal hydroxides, alkali metal carbonates, and alkali metals. Salts may be selected from one or more of the following groups (e.g., 2, 3, 4, or 5): sodium hydride, sodium hydroxide, sodium carbonate, potassium carbonate, Sodium salts and Potassium salts may also be selected from one or more of the following groups (e.g., two, three, four, or five): sodium hydroxide, sodium carbonate, potassium carbonate, Sodium salts and Potassium salts.

[0138] In one embodiment, the sodium hydroxide can be generated in situ from water and sodium hydride.

[0139] In one particular scheme, the aforementioned Sodium salts may be sodium methoxide, sodium 2-methyl-2-nonoxide, sodium tert-butoxide, sodium 1-adamantoxide, sodium isopropoxide, sodium ethoxide, sodium terpineol, sodium 3-ethyl-3-pentanol, sodium 2-methyl-2-hexanol, sodium 1,3-propanediol, sodium glycerol, sodium pentaerythritol, or sodium 2-methyl-2-pentanol.

[0140] In one particular scheme, the aforementioned Potassium salts may be potassium methoxide, potassium 2-methyl-2-nonoxide, potassium tert-butoxide, potassium 1-adamantoxide, potassium isopropoxide, potassium ethoxide, potassium terpineol, potassium 3-ethyl-3-pentanol, potassium 2-methyl-2-hexanol, potassium 1,3-propanediol, potassium glycerol, potassium pentaerythritol, or potassium 2-methyl-2-pentanol.

[0141] In one particular scheme, the aforementioned Sodium salts can be derived from It is generated in situ with sodium hydride.

[0142] In one particular scheme, the aforementioned Potassium salts can be derived from It is generated in situ with potassium hydride.

[0143] In one embodiment, when the alkali is sodium hydroxide, the sodium hydroxide can be generated in situ from water and sodium hydride. The amount of water can be a catalytic amount, and the generated sodium hydroxide participates in the reaction to regenerate water. The molar amount of sodium hydride can be the same as the molar amount of the alkali. That is, the sodium hydroxide can be added in the form of water and sodium hydride.

[0144] In one embodiment, when the amount of water is a catalytic amount, the catalytic amount refers to the molar ratio of water to the compound shown in Formula II, which can be (0.08–0.15):1 or 0.10:1.

[0145] In one embodiment, when the alkali is sodium hydroxide, the sodium hydroxide can be added directly in part and generated in situ by water and sodium hydride in part; the water can be generated by the reaction of the directly added sodium hydroxide. That is, sodium hydroxide can be added in the form of sodium hydroxide and sodium hydride, or in the form of water, sodium hydroxide, and sodium hydride.

[0146] In one scheme, when the alkali is When sodium salt is used, the aforementioned Sodium salts can be derived from It is generated in situ with sodium hydride, wherein, The amount can be the catalytic amount, and the amount generated is... Sodium salts participate in the reaction and are regenerated The molar amount of sodium hydride can be the same as the molar amount of the alkali. That is, the... Sodium salts can be used as It is added in the form of sodium hydride.

[0147] In one particular scheme, when the aforementioned When the amount can be a catalytic amount, the catalytic amount refers to: The molar ratio with the compound shown in Formula II can be (0.03 to 0.3):1, or it can be 0.03:1, 0.05:1, 0.06:1, 0.07:1, 0.123:1, 0.125:1, 0.165:1, 0.25:1 or 0.3:1.

[0148] In one scheme, when the alkali is When sodium salt is used, the aforementioned Sodium salt can be added directly in part, and partially added by... It is generated in situ with sodium hydride; the aforementioned Can be added directly Sodium salt is formed after participating in the reaction. That is, Sodium salts can be used as It can also be added in the form of sodium salt and sodium hydride, or in... It is added in the form of sodium salt and sodium hydride.

[0149] In one embodiment, the molar ratio of the base to the compound as shown in Formula II can be (2–4):1 {e.g., 2:1, 2.5:1 or 4:1}, or it can be (2–2.5):1.

[0150] In one embodiment, the condensation reaction can also be carried out in the presence of an initiator, wherein the initiator is...

[0151] R 1-II Hydrogen, C1 to C 10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0152] R 2-II Hydrogen, C1 to C 10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0153] R 3-II Hydrogen, C1 to C 10 Alkyl groups, C2-C 10 alkenyl or C1-C 10 alkoxy groups;

[0154] Or, R 2 R 3 Together with the carbon atoms attached to it, they form C6 to C6 carbon atoms. 10 aryl group, C6-C6 substituted with one or more hydroxyl groups 10 The aryl group, or a 5- to 10-membered heteroaryl group; wherein the heteroatom in the heteroaryl group is selected from one or more of N, O and S, and the number of heteroatoms is 1, 2 or 3;

[0155] R 4-II It is O;

[0156] R 5-II It is O.

[0157] In a certain scheme, when R 1-II C1~C 10 When alkyl groups are present, the C1-C1 group is... 10 The alkyl group can be a C1 to C4 alkyl group, or it can be a methyl group.

[0158] In a certain scheme, when R 1-II For C2~C 10 When the alkenyl group is present, the C2-C 10 The alkenyl group can be a C2 to C5 alkenyl group, or it can be a 3-methyl-2-buten-1-yl group.

[0159] In a certain scheme, when R 1-II C1~C 10 When the alkoxy group is present, the C1-C1... 10 The alkoxy group can be a C1 to C4 alkoxy group, or it can be a methoxy group.

[0160] In a certain scheme, when R 2-II C1~C 10 When alkyl groups are present, the C1-C1 group is... 10 The alkyl group can be a C1 to C4 alkyl group, or it can be a methyl group.

[0161] In a certain scheme, when R 2-II For C2~C 10 When the alkenyl group is present, the C2-C 10 The alkenyl group can be a C2 to C5 alkenyl group, or it can be a 3-methyl-2-buten-1-yl group.

[0162] In a certain scheme, when R 2-II C1~C 10 When the alkoxy group is present, the C1-C1... 10 The alkoxy group can be a C1 to C4 alkoxy group, or it can be a methoxy group.

[0163] In a certain scheme, when R 3-II C1~C 10 When alkyl groups are present, the C1-C1 group is... 10 The alkyl group can be a C1 to C4 alkyl group, or it can be a methyl group.

[0164] In a certain scheme, when R 3-II For C2~C 10 When the alkenyl group is present, the C2-C 10 The alkenyl group can be a C2 to C5 alkenyl group, or it can be a 3-methyl-2-buten-1-yl group.

[0165] In a certain scheme, when R 3-II C1~C 10 When the alkoxy group is present, the C1-C1... 10 The alkoxy group can be a C1 to C4 alkoxy group, or it can be a methoxy group.

[0166] In a certain scheme, when R 2-II R 3-II Together with the carbon atoms attached to it, they form C6 to C6 carbon atoms. 10 When the aryl group is present, the C6-C 10 The aryl group can be phenyl.

[0167] In a certain scheme, when R 2-II R 3-II Together with the carbon atom attached thereto, they form C6-C atoms that are substituted with one or more hydroxyl groups. 10 When the aryl group is present, the C6-C 10 The aryl group can be phenyl.

[0168] In one scheme, the R... 1-II With the aforementioned R 1 Same; the R mentioned above 2-II With the aforementioned R 2 Same; the R mentioned above 3-II With the aforementioned R 3 same.

[0169] In one particular scheme, the aforementioned It can be 1,4-hydroquinone.

[0170] In one embodiment, the molar ratio of the initiator to the compound shown in Formula II can be (0.005–1):1 {e.g., 0.01:1, 0.025:1, 0.05:1, 0.075:1, 0.10:1, 0.15:1, 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, or 0.8:1}, or (0.025–0.10):1, or (0.05–0.10):1.

[0171] In one embodiment, the initiator The initiator can be generated in situ from the compound shown in Formula II above and a reducing agent. That is, by directly adding a reducing agent (but without adding a separate initiator), the initiator can be generated in situ in the reaction solution. In other words, the condensation reaction can also be carried out in the presence of a reducing agent.

[0172] In one embodiment, the reducing agent is a conventional reducing agent for quinone compounds, which can be... R 7-1 and R 7-2 It is an alkyl group that is independently C1 to C4.

[0173] In one particular scheme, the aforementioned Can be

[0174] In one embodiment, the molar ratio of the reducing agent to the compound shown in Formula II can be (0.005–1):1 {e.g., 0.01:1, 0.025:1, 0.05:1, 0.075:1, 0.10:1, 0.15:1, 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, or 0.8:1}, or (0.025–0.10):1, or (0.05–0.10):1.

[0175] In one embodiment, the molar ratio of the compound shown in Formula III to the compound shown in Formula II can be (0.1 to 2.0):1 {for example, 0.2:1, 0.4:1, 0.5:1, 1:1, 1.05:1, 1.65:1 or 1.70:1}, or it can also be (0.2 to 1.70):1.

[0176] In one embodiment, the temperature of the condensation reaction can be 35℃ to 100℃ (e.g., 50℃, 60℃, 65℃, 70℃, 75℃, 80℃, 85℃, 90℃ or 95℃), or 40℃ to 100℃, or even 70℃ to 80℃.

[0177] The process of the condensation reaction can be monitored by means of TLC, HPLC and other methods. Those skilled in the art can terminate the reaction based on the reaction scale, the degree of conversion of raw materials, the reaction efficiency (i.e. the relationship between yield and reaction time), the formation of impurities, etc., in order to obtain the preferred yield and purity.

[0178] In one embodiment, the reaction time of the condensation reaction can be from 0.1 hours to 336 hours (e.g., 3 hours, 5 hours, 6 hours, 12 hours, 21 hours, 24 hours, 28 hours, 30 hours, 36 hours, 40 hours, 48 ​​hours, 60 hours, 72 hours, 96 hours, 100 hours, 120 hours, 144 hours, or 168 hours), or it can be from 5 hours to 100 hours.

[0179] In one approach, the post-treatment of the condensation reaction may include the following steps: removal of the solid followed by column chromatography.

[0180] In one embodiment, the method for removing solids may be centrifugation or filtration.

[0181] In one embodiment, the condensation reaction may have the following reaction parameters: the condensation reaction is carried out in the presence of a protective gas; the condensation reaction is carried out in an organic solvent, wherein the organic solvent is a halogenated aromatic hydrocarbon solvent, and the molar volume ratio of the compound represented by Formula II to the organic solvent is 0.1 mol / L to 0.3 mol / L; the base is sodium hydroxide or... Sodium salt, R x for R x-2 The base can be a C1-C7 straight-chain alkyl group, and the molar ratio of the base to the compound shown in Formula II is (2-4):1; the condensation reaction is carried out in... The above is carried out in the presence of the present, The molar ratio of the compound shown in Formula II to the compound shown in Formula III is (0.025–0.10):1; the molar ratio of the compound shown in Formula III to the compound shown in Formula II is (0.2–2.0):1; the temperature of the condensation reaction is 40°C–100°C.

[0182] In one embodiment, the condensation reaction may have the following reaction parameters: the condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or o-dichlorobenzene, and the molar volume ratio of the compound represented by Formula II to the chlorobenzene or o-dichlorobenzene is 0.1 mol / L to 0.2 mol / L; the base is... Sodium salt, Rx is For tert-butyl, The molar ratio of the base to the compound shown in Formula II is (2–2.5):1; the condensation reaction is still underway. The above is carried out in the presence of the present, The molar ratio of the compound shown in Formula II to the compound shown in Formula III is (0.05–0.10):1; the molar ratio of the compound shown in Formula III to the compound shown in Formula II is (0.2–1.70):1; the temperature of the condensation reaction is 70°C–80°C.

[0183] In one embodiment, the condensation reaction may have the following reaction parameters: the condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or o-dichlorobenzene, and the molar volume ratio of the compound represented by Formula II to the chlorobenzene or o-dichlorobenzene is 0.1 mol / L to 0.2 mol / L; the base is sodium hydride and... Sodium salt, R x for For tert-butyl, The molar ratio of the base to the compound shown in Formula II is (2–2.5):1; the condensation reaction is still underway. The above is carried out in the presence of the present, The molar ratio of the compound shown in Formula II to the compound shown in Formula III is (0.05–0.10):1; the molar ratio of the compound shown in Formula III to the compound shown in Formula II is (0.2–1.70):1; the temperature of the condensation reaction is 70°C–80°C.

[0184] In one embodiment, the condensation reaction may have the following reaction parameters: the condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or o-dichlorobenzene, and the molar volume ratio of the compound represented by Formula II to the chlorobenzene or o-dichlorobenzene is 0.1 mol / L to 0.2 mol / L; the base is sodium hydride and... R x for For tert-butyl, The molar ratio of the base to the compound shown in Formula II is (2-2.5):1. The molar ratio of the compound to that shown in Formula II is (0.03–0.3):1; the condensation reaction is still ongoing. The above is carried out in the presence of the present, The molar ratio of the compound shown in Formula II to the compound shown in Formula III is (0.05–0.10):1; the molar ratio of the compound shown in Formula III to the compound shown in Formula II is (0.2–1.70):1; the temperature of the condensation reaction is 70°C–80°C.

[0185] In this invention, unless otherwise specified, the terms have the following meanings:

[0186] The term "multiple" refers to 2, 3, 4, or 5.

[0187] The term "multiple" refers to two, three, four, or five kinds.

[0188] The term "basicity" is defined according to the Brønsted-Laurent definition, which refers to a substance's ability to bind with protons; the stronger the binding ability, the stronger the basicity. The basicity of a substance can be characterized by the pKa value of its conjugate acid; the higher the pKa of the conjugate acid, the stronger the basicity of the substance. The pKa measurement method can be found in Lange's Handbook of Chemistry, p. 13. thThe measurement method described in Edition, pages 5-93 or J. Am. Chem. Soc. 1975, 97, 7006-7014. "A substance is more basic than sodium phenolate" means that, in the same solvent (or reaction system), the pKa of the conjugate acid of the substance is greater than the pKa of phenol. For example, when using the method described in the literature (J. Am. Chem. Soc. 1975, 97, 7006-7014), the pKa of phenol, the conjugate acid of sodium phenolate, measured in dimethyl sulfoxide at 25°C, is 18.0 (Acc. Chem. Res. 1988, 21, 456-463). If the pKa of the conjugate acid of a certain base is greater than 18.0 in dimethyl sulfoxide at 25°C, then the base is considered more basic than sodium phenolate; otherwise, it is considered less basic than sodium phenolate.

[0189] The term "halogen" refers to the elements fluorine, chlorine, bromine, or iodine.

[0190] The term "hydrocarbon group" refers to a group formed by the loss of one hydrogen atom in a hydrocarbon compound.

[0191] The term "alkyl" refers to a saturated straight-chain or branched hydrocarbon group containing one or more carbon atoms. Alkyl groups containing n carbon atoms are represented by Cn. n It means that C m ~C n This indicates that the alkyl group contains at least m and at most n carbon atoms. Representative saturated straight-chain alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, and n-pentyl; representative saturated branched alkyl groups include isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, and neopentyl.

[0192] The term "cycloalkyl" refers to a saturated monocyclic or polycyclic (e.g., spirocyclic, fused-ring, or bridged-ring) alkyl group that may have 3-10 or 3-6 ring carbon atoms. Examples of cycloalkyl groups include, but are not limited to, adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0193] The term "alkoxy" refers to -O-(alkyl), where "alkyl" is an alkyl group as defined above.

[0194] The term "alkenyl" refers to an unsaturated straight-chain or branched hydrocarbon group containing one or more double bonds and multiple carbon atoms. Representative straight-chain alkenyl groups include, but are not limited to, vinyl, propenyl, and allyl.

[0195] The term "cycloalkenyl" refers to an unsaturated (but not aromatic), monocyclic or polycyclic (e.g., spirocyclic, fused-ring, or bridged-ring) cyclic hydrocarbon group containing one or more double bonds and multiple carbon atoms. Representative cycloalkenyl groups include, but are not limited to, cyclopentenyl and cyclohexenyl.

[0196] The term "aryl" refers to either phenyl or naphthyl.

[0197] The term "heteroaryl" refers to an aromatic group containing one, two, or three independent 5- or 6-membered monocyclic or 9- or 10-membered bicyclic (e.g., fused or bridged rings) groups selected from nitrogen, oxygen, and sulfur. When it is bicyclic, at least one ring is aromatic, including but not limited to furanyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiopheneyl, isozolyl, oxazolyl, diazolyl, imidazoleyl, pyrroleyl, pyrazolyl, triazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzimidazolyl, indolyl, inzolyl, benzothiazolyl, benziisothiazolyl, benzozolyl, benziisozolyl, quinolinyl, isoquinolinyl, etc.

[0198] Without violating common sense in the field, the above-mentioned preferred conditions can be combined arbitrarily to obtain various preferred embodiments of the present invention.

[0199] The reagents and raw materials used in this invention can all be obtained commercially or prepared according to published literature.

[0200] The positive and progressive effects of this invention are: (1) one-pot one-step synthesis without intermediate separation and purification; (2) inexpensive and readily available raw materials; (3) no protective groups are used, reducing the generation of hazardous waste; (4) no heavy metal reagents are used, resulting in no harmful metal residues; (5) no external oxidants are used; (6) no strong Lewis acid reagents are used; (7) simple reaction conditions and high product selectivity. Detailed Implementation

[0201] The present invention is further illustrated below by way of embodiments, but the invention is not limited to the scope of the embodiments described herein. Experimental methods in the following embodiments that do not specify specific conditions were performed according to conventional methods and conditions, or as selected according to the product instructions.

[0202] Example 1

[0203]

[0204] In a dry 100 mL flask, a magnetic stir bar, 1.36 g (10 mmol, 1 equivalent) of 2,3-dimethyl-p-benzoquinone, 126 mg (0.5 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 50 mL of dry chlorobenzene, 1.73 g (16.5 mmol, 1.65 equivalent) of 1-chloro-3-methyl-2-butene (isopentene chloride), and 237 mg (1.5 mmol, 0.15 equivalent) of 2-methyl-2-nonanol were added sequentially. After the solids dissolved, 0.8 g of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 0.5 g of sodium hydride, approximately 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen through the reaction system. The flask was heated to 80°C and the reaction was stirred for 48 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 1.69 g of 2,3-dimethyl-5-(3-methyl-2-buten-1-yl)-p-benzoquinone, with a yield of 83%. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 6.47 (d, J=1.9Hz, 1H), 5.19-5.10 (m, 1H), 3.11 (d, J=7.3Hz, 2H), 2.06-1.99 (m, 6H), 1.76 (s, 3H), 1.63 (d, J=1.7Hz, 3H). 13 C-NMR (101MHz, CDCl3) δ (ppm) 187.89, 187.69, 148.02, 141.01, 140.56, 136.03, 132.05, 118.33, 27.59, 25.75, 17.74, 12.39, 12.04.

[0205] Example 2

[0206]

[0207] In a dry 10 mL flask, a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 6.3 mg (0.025 mmol, 0.05 equivalent), 2.5 mL of dry chlorobenzene, 87 mg (0.83 mmol, 1.66 equivalent) of 1-chloro-3-methyl-2-butene (isopentene chloride), and 23.7 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol were added sequentially. After the solids dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen through the reaction system. The flask was heated to 80°C and the reaction was stirred for 48 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 97 mg of 2,6-dimethyl-3-(3-methyl-2-buten-1-yl)-p-benzoquinone, with a yield of 95%. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 6.55 (d, J=2.2Hz, 1H), 4.94 (t, J=7.1Hz, 1H), 3.18 (d, J=7.0Hz, 2H), 2.06-2.01 (m, 6H), 1.74 (s, 3H), 1.67 (s, 3H). 13 C-NMR (126MHz, CDCl3) δ (ppm) 188.46, 187.19, 145.23, 143.42, 140.71, 133.79, 133.12, 119.23, 25.71, 25.40, 17.97, 15.88, 12.18.HRMS (ESI)calcd.For C 13 H 17 O2 + :205.1223.Found:205.1221(MH + ).

[0208] Examples 3-31

[0209] After changing the types and amounts of raw materials in Example 2 above, Examples 3 to 31 are formed. The specific changes in the types and amounts of materials are shown in the table below:

[0210]

[0211]

[0212]

[0213] Note: The equivalents in the table above are all based on 2,6-dimethyl-p-benzoquinone as 1 equivalent. HE = 2,6-dimethyl-3,5-bis(ethoxyacyl)-1,4-dihydropyridine; HQ = 1,4-hydroquinone.

[0214] The pKa of K2CO3 is 10.25, which is slightly higher than that of sodium phenolate (9.98).

[0215] In Example 10, the yield was 56% based on the amount of sodium tert-butoxide added; in Example 11, the yield was 47% based on the amount of sodium tert-butoxide added.

[0216] Example 32

[0217]

[0218] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 6.3 mg (0.025 mmol, 0.05 equivalent), 2.5 mL of dry chlorobenzene, 143 mg (0.83 mmol, 1.66 equivalent) of 1-chloro-3,7-dimethyl-2,6-dioctene (geranyl chloride), and 11.9 mg (0.15 mmol, 0.15 equivalent) of 2-methyl-2-nonanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) to the reaction flask. Then connect an air condenser to the round-bottom flask, purging with nitrogen gas and continuously bubbling nitrogen into the reaction system. The flask was heated to 80°C and the reaction mixture was stirred for 36 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes, and the supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 115.5 mg of 2,6-dimethyl-3-(3,7-dimethyl-2,6-diocten-1-yl)-p-benzoquinone, in 85% yield. The product was a yellow oily liquid. 1 H NMR (400MHz, CDCl3) δ (ppm) 6.55 (q, J=1.6Hz, 1H), 5.07-4.99 (m, 1H), 4.94 (tq, J=7.0, 1.3Hz, 1H), 3.19 (d, J= 6.9Hz, 2H), 2.03 (d, J=1.7Hz, 8H), 1.97 (dd, J=8.9, 6.2Hz, 2H), 1.73 (d, J=1.4Hz, 3H), 1.65 (d, J=1.5Hz, 3H). 13C NMR (101MHz, CDCl3) δ (ppm) 188.47, 187.15, 145.23, 143.53, 140.80, 137.32, 133.12, 131.54, 124.02, 119.17, 39.67, 26.53, 25.68, 25.25, 17.68, 16.30, 15.89, 12.18.HRMS(ESI)calcd.For C 18 H 25 O2 + :273.1849.Found:273.1844(MH + )

[0219] Example 33

[0220]

[0221] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 6.3 mg (0.025 mmol, 0.05 equivalent), 2.5 mL of dry chlorobenzene, 200 mg (0.83 mmol, 1.66 equivalent) of 1-chloro-3,7,11-trimethyl-2,6,10-dodecanetriene (farnesyl chloride), and 11.9 mg (0.15 mmol, 0.15 equivalent) of 2-methyl-2-nonanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) to the reaction flask. Then connect an air condenser to the round-bottom flask, purging nitrogen gas and continuously bubbling nitrogen into the reaction system. The flask was heated to 80°C and the reaction mixture was stirred for 36 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes, and the supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 133.5 mg of 2,6-dimethyl-3-(3,7,11-trimethyl-2,6,10-dodecanetrien-1-yl)-p-benzoquinone, with a yield of 78%. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 6.47 (q, J=1.6Hz, 1H), 5.07-4.93 (m, 2H), 4.87 (t, J=14.8Hz, 1H), 3.11 (d, J=7.0Hz, 2H), 2.03-1.93 ( m, 10H), 1.91 (d, J=7.6Hz, 2H), 1.86 (dd, J=9.4, 6.2Hz, 2H), 1.67 (d, J=1.4Hz, 3H), 1.60 (t, J=2.7Hz, 3H), 1.51 (s, 3H), 1.50 (s, 3H).13 C-NMR (101MHz, CDCl3) δ (ppm) 188.44, 187.14, 145.22, 143.51, 140.76, 137.36, 135.18, 133.11, 131.29 , 124.33, 123.85, 119.15, 39.70, 39.67, 26.75, 26.43, 25.70, 25.27, 17.67, 16.32, 16.02, 15.87, 12.19.

[0222] Example 34

[0223]

[0224] In a dry 10 mL flask, add in sequence a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 6.3 mg (0.025 mmol, 0.05 equivalent), 2.5 mL of dry chlorobenzene, 259 mg (0.83 mmol, 1.66 equivalent) of (2E,7R,11R)-1-chloro-3,7,11,15-tetramethyl-2-hexadecene (chlorophylloyl chloride), and 11.9 mg (0.15 mmol, 0.15 equivalent) of 2-methyl-2-nonanol. After the solid dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen into the reaction system. The flask was heated to 80°C and the reaction was stirred for 60 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 109.5 mg of 3,5-dimethyl-2-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecene-1-yl)-p-benzoquinone, in 53% yield. The product was a yellow oily liquid. 1H-NMR (400MHz, CDCl3) δ (ppm) 6.55 (d, J = 1.8Hz, 1H), 4.98-4.89 (m, 1H), 3.19 (d, J = 7.0Hz, 2H ), 2.03 (d, J=2.5Hz, 6H), 1.95-1.89 (m, 2H), 1.72 (s, 3H), 1.67-1.62 (m, 1H), 1.52 (dt, J=13.3 , 6.6Hz, 1H), 1.33 (ddt, J=24.5, 9.1, 4.7Hz, 5H), 1.28-1.17 (m, 6H), 1.14 (ddd, J=9.0, 5.7, 1 .9Hz, 3H), 1.05 (ddt, J=18.0, 10.3, 7.7Hz, 3H), 0.86 (d, J=6.7Hz, 6H), 0.83 (t, J=6.3Hz, 6H). 13 C-NMR(126MHz, CDCl3)δ(ppm) 188.45, 187.15, 145.20, 143.56, 140.74, 137.78, 133.12, 118.85, 40.00, 39.38, 37.43, 37.39, 37.30, 36 .64, 32.79, 32.65, 27.98, 25.28, 25.26, 24.80, 24.47, 22.73, 22.63, 19.75, 19.72, 16.22, 15.88, 12.20.

[0225] Example 35

[0226]

[0227] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 6.3 mg (0.025 mmol, 0.05 equivalent), 2.5 mL of dry chlorobenzene, 100 mg (0.83 mmol, 1.66 equivalent) of allyl bromide, and 23.7 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) to the reaction flask. Then connect an air condenser to the round-bottom flask to purge nitrogen and continuously bubble nitrogen through the reaction system. Heat the flask to 80°C and stir the reaction for 48 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 28 mg of 3,5-dimethyl-2-allyl-p-benzoquinone, with a yield of 32%. The product was a yellow oily liquid. 1H-NMR (400MHz, CDCl3) δ (ppm) 6.57 (s, 1H), 5.81-5.63 (m, 2H), 5.09 (d, J = 9.3Hz, 1H), 3.24 (d, J = 6.6Hz, 2H), 2.05 (s, 6H).

[0228] Example 36

[0229]

[0230] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 6.3 mg (0.025 mmol, 0.05 equivalent), 2.5 mL of dry chlorobenzene, 112 mg (0.83 mmol, 1.66 equivalent) of trans-1-bromo-2-butene (crotonyl bromide), and 23.7 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents). Then connect an air condenser to the round-bottom flask, purging with nitrogen and continuously bubbling nitrogen into the reaction system. Heat the flask to 80°C and stir the reaction for 48 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 46.5 mg of 3,5-dimethyl-2-(2-buten-1-yl)-p-benzoquinone, with a yield of 49%. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 6.55 (q, J = 1.7Hz, 1H), 5.55-5.42 (m, 1H), 5.41- 5.29 (m, 1H), 3.16 (d, J=6.3Hz, 2H), 2.04 (s, 6H), 1.62 (dt, J=6.4, 1.5Hz, 3H). 13 C-NMR (101MHz, CDCl3) δ (ppm) 188.37, 187.04, 145.33, 142.45, 141.12, 133.09, 127.36, 125.71, 29.13, 17.87, 15.90, 12.05.

[0231] Example 37

[0232]

[0233] In a dry 10 mL flask, a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 6.3 mg (0.025 mmol, 0.05 equivalent), 2.5 mL of dry chlorobenzene, 134.5 mg (0.83 mmol, 1.66 equivalent) of cis-1-bromo-2-hexene, and 23.7 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol were added sequentially. After the solids dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen through the reaction system. The flask was heated to 80°C and the reaction was stirred for 48 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 30 mg of 3,5-dimethyl-2-(cis-2-hexen-1-yl)-p-benzoquinone, with a yield of 28%. The product was a yellow oily liquid. 1 H-NMR (500MHz, CDCl3) δ (ppm) 6.55 (q, J=1.7Hz, 1H), 5.50-5.40 (m, 1H), 5.19 (dtt, J=10.6, 7.1, 1.7Hz, 1H), 3.24 (d, J= 8.6Hz, 2H), 2.15 (qd, J=7.4, 1.7Hz, 2H), 2.05 (s, 3H), 2.04-2.03 (m, 3H), 1.42 (h, J=7.4Hz, 2H), 0.94 (t, J=7.4Hz, 3H).

[0234] Example 38

[0235]

[0236] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 6.3 mg (0.025 mmol, 0.05 equivalent), 2.5 mL of dry chlorobenzene, 125.5 mg (0.83 mmol, 1.66 equivalent) of trans-1-chloro-3-phenyl-2-propenyl (cinnamyl chloride), and 23.7 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents). Then connect an air condenser to the round-bottom flask, purging with nitrogen and continuously bubbling nitrogen into the reaction system. Heat the flask to 80°C and stir the reaction for 48 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 114.5 mg of 3,5-dimethyl-2-(trans-3-phenyl-2-propen-1-yl)-p-benzoquinone, with a yield of 91%. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 7.34-7.23 (m, 4H), 7.26-7.15 (m, 1H), 6.59 (q, J=1.6Hz, 1H), 6.42 (dt, J=15.8 , 1.6Hz, 1H), 6.11 (dt, J=15.9, 6.7Hz, 1H), 3.39 (dd, J=6.8, 1.6Hz, 2H), 2.10 (s, 3H), 2.05 (d, J=1.7Hz, 3H). 13 C-NMR (101MHz, CDCl3) δ (ppm) 188.24, 186.93, 145.52, 141.75, 141.62, 137 .03, 133.12, 131.90, 128.52, 127.38, 126.11, 124.91, 29.54, 15.95, 12.25.

[0237] Example 39

[0238]

[0239] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 6.3 mg (0.025 mmol, 0.05 equivalent), 2.5 mL of dry chlorobenzene, 132 mg (0.83 mmol, 1.66 equivalent) of 1-bromo-2-cyclohexene, and 23.7 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) to the reaction flask. Then connect an air condenser to the round-bottom flask, purging with nitrogen and continuously bubbling nitrogen into the reaction system. Heat the flask to 80°C and stir the reaction for 48 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 51 mg of 3,5-dimethyl-2-(2-cyclohexen-1-yl)-p-benzoquinone, with a yield of 47%. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 6.55 (q, J = 1.6Hz, 1H), 5.83-5.75 (m, 1H), 5.5 1(dp, J=10.1, 2.0Hz, 1H), 3.88 (ddt, J=8.3, 5.8, 2.8Hz, 1H), 2.11 (td, J=4.0 , 1.8Hz, 1H), 2.09 (s, 4H), 2.03 (d, J=1.6Hz, 3H), 1.88 (dt, J=12.9, 3.7Hz, 1H ), 1.79 (dtd, J = 11.3, 4.1, 2.3Hz, 1H), 1.74-1.62 (m, 1H), 1.62-1.51 (m, 1H). 13 C-NMR (126MHz, CDCl3) δ (ppm) 188.84, 187.04, 146.79, 145.11, 142.01, 133.41, 129.10, 127.06, 34.18, 27.79, 24.53, 22.68, 15.80, 12.51.

[0240] Example 40

[0241]

[0242] In a dry 10 mL flask, add in sequence a magnetic stir bar, 102.5 mg (0.5 mmol, 1 equivalent) of 3,5-dimethyl-2-(3-methyl-2-buten-1-yl)-p-benzoquinone, 6.3 mg (0.025 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 125.5 mg (0.83 mmol, 1.66 equivalent) of trans-1-chloro-3-phenyl-2-propene (cinnamyl chloride), and 23.7 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol. After the solid dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen into the reaction system. The flask was heated to 80°C and the reaction mixture was stirred for 36 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 110.5 mg of 3,5-dimethyl-2-trans-cinnamyl-6-isopentenyl-p-benzoquinone, in 69% yield. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 7.36-7.25 (m, 4H), 7.21-7.17 (m, 1H), 6.44-6.37 (m, 1H), 6.13 (dt, J=15.8, 6.8Hz, 1H), 4.98-4.91 (m, 1H), 3.40 (dd, J=6.7, 1.6Hz, 2H), 3.21 (d, J=7.1Hz, 2H), 2.08 (s, 3H), 2.04 (s, 3H), 1.76-1.74 (m, 3H), 1.67 (d, J=1.5Hz, 3H).

[0243] Example 41

[0244]

[0245] In a dry 10 mL flask, add in sequence a magnetic stir bar, 68 mg (0.5 mmol, 1 equivalent) of 2,3-dimethyl-p-benzoquinone, 6.3 mg (0.025 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 341 mg (0.52 mmol, 1.05 equivalent) of all-E-1-chloro-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexadecanononene (solanyl chloride), and 23.7 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol. After the solid dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen into the reaction system. The flask was heated to 80°C and the reaction mixture was stirred for 36 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 179.8 mg of the product, quinone, in 48% yield. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 6.49-6.45 (m, 1H), 5.11 (t, J=7.2Hz, 9H), 3.12 (d, J=7.2Hz, 2H), 2.06 (t, J=7. 2Hz, 16H), 2.03 (s, 3H), 2.01 (s, 3H), 1.98 (dd, J=9.9, 5.5Hz, 16H), 1.68 (s, 6H), 1.62 (s, 3H), 1.60 (s, 21H).

[0246] Example 42

[0247]

[0248] In a dry 10 mL flask, add in sequence the following ingredients: a magnetic stir bar, 75 mg (0.5 mmol, 1 equivalent) of 2,3,5-trimethyl-p-benzoquinone, 12.6 mg (0.05 mmol, 0.1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 259 mg (0.83 mmol, 1.66 equivalent) of (2E,7R,11R)-1-chloro-3,7,11,15-tetramethyl-2-hexadecene (chlorophylloyl chloride), and 23.8 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol. After the solid dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen into the reaction system. The flask was heated to 80°C and the reaction mixture was stirred for 100 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 134.5 mg of 2,3,5-trimethyl-6-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecene-1-yl)-p-benzoquinone, in 63% yield. The product was a brown oily liquid. 1 H-NMR (500MHz, CDCl3) δ (ppm) 4.94 (t, J = 7.0Hz, 1H), 3.20 (d, J = 6.9Hz, 2H), 2.02 (s , 3H), 2.01 (s, 6H), 1.92 (td, J=7.4, 3.8Hz, 2H), 1.73 (s, 3H), 1.64 (d, J=17.4Hz, 1H ), 1.52 (hept, J = 6.7Hz, 1H), 1.43 (s, 1H), 1.40-1.32 (m, 2H), 1.31-1.18 (m, 10H), 1 .18-1.09 (m, 2H), 1.09-1.00 (m, 2H), 0.86 (d, J=6.7Hz, 6H), 0.83 (t, J=6.3Hz, 6H). 13 C-NMR (126MHz, CDCl3) δ (ppm) 187.95, 187.02, 143.24, 140.37, 140.32, 140.25, 137.51, 119.20, 40.02, 39.38, 37.43, 37.3 9, 37.30, 36.65, 32.79, 32.65, 27.98, 25.57, 25.29, 24.80, 24.47, 22.72, 22.63, 19.74, 19.72, 16.21, 12.38, 12.36, 12.17.

[0249] Example 43

[0250]

[0251] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 86 mg (0.5 mmol, 1 equivalent) of 2-methylnaphthoquinone, 6.3 mg (0.025 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 87 mg (0.83 mmol, 1.66 equivalent) of 1-chloro-3-methyl-2-butene (isopentene chloride), and 13.9 mg (0.088 mmol, 0.175 equivalent) of 2-methyl-2-nonanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) to the reaction flask. Then connect an air condenser to the round-bottom flask to purge nitrogen and continuously bubble nitrogen through the reaction system. Heat the flask to 80°C and stir the reaction for 30 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 58 mg of 2-methyl-3-isopentenyl-1,4-naphthoquinone, with a yield of 48%. The product was a yellow oily liquid. 1 H-NMR (500MHz, CDCl3) δ (ppm) 8.08 (dt, J=5.3, 2.7Hz, 2H), 7.68 (dd, J=5.9, 3.3Hz, 2H) , 5.01 (d, J=7.2Hz, 1H), 3.36 (d, J=7.0Hz, 2H), 2.19 (s, 3H), 1.80 (s, 3H), 1.69 (s, 3H). 13 C NMR (101MHz, CDCl3) δ (ppm) 185.50, 184.58, 146.08, 143.30, 133.98, 133.35, 133.30, 132.19, 132.15, 126.31, 126.20, 119.21, 26.15, 25.75, 18.07, 12.68.

[0252] Examples 44-45

[0253] By changing the types and amounts of raw materials in Example 43 above, Examples 44 and 45 are formed. The specific changes in the types and amounts of materials are shown in the table below:

[0254]

[0255] Example 46

[0256]

[0257] In a dry 10 mL flask, a magnetic stir bar, 86 mg (0.5 mmol, 1 equivalent) of 2-methylnaphthoquinone, 6.3 mg (0.025 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 259 mg (0.83 mmol, 1.66 equivalent) of (2E,7R,11R)-1-chloro-3,7,11,15-tetramethyl-2-hexadecene (chlorophylloyl chloride), and 11.9 mg (0.075 mmol, 0.15 equivalent) of 2-methyl-2-nonanol were added sequentially. After the solids dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen through the reaction system. The flask was heated to 80°C and the reaction mixture was stirred for 120 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes, and the supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 166 mg of 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecen-1-yl)-1,4-naphthoquinone (vitamin K1), with a yield of 82%. The product was a yellow oily liquid. 1 H-NMR (500MHz, CDCl3) δ (ppm) 8.07 (dq, J=7.0, 4.0, 3.5Hz, 2H), 7.68 (dd, J=5.8, 3.2Hz, 2H), 5 .01 (t, J=6.9Hz, 1H), 3.37 (d, J=6.9Hz, 2H), 2.19 (s, 3H), 1.99-1.90 (m, 2H), 1.78 (s, 3H), 1.6 6 (d, J=21.1Hz, 1H), 1.55-1.48 (m, 1H), 1.42 (s, 1H), 1.34 (tt, J=10.6, 4.9Hz, 2H), 1.30-1.17 (m, 10H), 1.17-1.08 (m, 2H), 1.03 (m, 2H), 0.86 (d, J=6.6Hz, 6H), 0.82 (dd, J=6.6, 3.9Hz, 6H). 13C-NMR (126MHz, CDCl3) δ (ppm) 185.47, 184.54, 146.22, 146.21, 143.34, 137.96, 133.33, 133.27, 132.21, 132.16, 126.31, 126.19, 118.82, 40 .04, 39.38, 37.42, 37.38, 37.30, 36.65, 32.78, 32.65, 27.98, 26.01, 2 5.29, 24.82, 24.80, 24.46, 22.73, 22.64, 19.74, 19.72, 16.32, 12.70.

[0258] Example 47

[0259] Example 47 is formed by changing the types and amounts of raw materials used in Example 46 above. The specific changes in the types and amounts of materials are shown in the table below:

[0260] Example Substitutes for 2-methyl-2-nonanol, and the equivalent amount of such substitutes. Time / h Yield / % 47 2-Methyl-2-pentanol, 0.1 65 71

[0261] Example 48

[0262]

[0263] In a dry 10 mL flask, add in sequence a magnetic stir bar, 86 mg (0.5 mmol, 1 equivalent) of 2-methylnaphthoquinone, 6.3 mg (0.025 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 139 mg (0.2 mmol, 0.4 equivalent) of all-E-1-bromo-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexadecanononene (solanyl bromide), and 11.9 mg (0.075 mmol, 0.15 equivalent) of 2-methyl-2-nonanol. After the solid dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen through the reaction system. The flask was heated to 80°C and the reaction mixture was stirred for 36 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 42.5 mg of vitamin K2-MK9 in 91% yield (based on solanesyl bromide). The product was a yellow solid. 1H-NMR (500MHz, CDCl3) δ (ppm) 8.07 (dq, J=6.9, 4.1, 3.5Hz, 2H), 7.67 (dd, J=5.8, 3.3Hz, 2H), 5.14-4.94 (m, 9H), 3.37 (d, J=6.9H z, 2H), 2.19 (d, J=2.5Hz, 3H), 2.06 (t, J=7.5Hz, 16H), 2.02-1.95 (m, 16H), 1.79 (s, 3H), 1.68 (s, 3H), 1.60 (s, 21H), 1.56 (s, 3H)

[0264] Example 49

[0265]

[0266] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 91 mg (0.5 mmol, 1 equivalent) of 2,3-dimethoxy-5-methyl-p-benzoquinone, 12.6 mg (0.05 mmol, 0.1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 123.7 mg (0.83 mmol, 1.66 equivalent) of 1-bromo-3-methyl-2-butene (isopentene bromide), and 39.7 mg (0.25 mmol, 0.5 equivalent) of 2-methyl-2-nonanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) to the reaction flask. Then connect an air condenser to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen through the reaction system. The flask was heated to 80°C and the reaction mixture was stirred for 21 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes, and the supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 77.6 mg of 2,3-dimethoxy-5-methyl-6-(3-methyl-2-buten-1-yl)-p-benzoquinone, in 62% yield. The product was an orange oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 4.94 (t, J=7.3Hz, 1H), 4.00 (s, 3H), 3.98 (s, 3H), 3.17 (d, J=7.1Hz, 2H), 2.02 (s, 3H), 1.74 (s, 3H), 1.68 (s, 3H).

[0267] Example 50

[0268]

[0269] In a dry 10 mL flask, add in sequence the following ingredients: a magnetic stir bar, 91 mg (0.5 mmol, 1 equivalent) of 2,3-dimethoxy-5-methyl-p-benzoquinone, 12.6 mg (0.05 mmol, 0.1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry o-dichlorobenzene, 162 mg (0.25 mmol, 0.5 equivalent) of all-E-1-chloro-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexadecanononene (solanyl chloride), and 23.8 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol. After the solid dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen into the reaction system. The flask was heated to 100°C and the reaction was stirred for 42 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 115 mg of coenzyme Q9 (CoQ9), in 58% yield (based on solanesyl chloride). The product was a yellow solid. 1 H-NMR (500MHz, CDCl3) δ (ppm) 5.11 (m, 8H), 4.94 (d, J = 7.8Hz, 1H), 3.99 (d, J = 2.5Hz, 3H), 3.98 (s, 3H), 3.18 (d, J = 6.9Hz, 2H), 2.06 (t, J=7.5Hz, 16H), 2.01 (s, 3H), 1.99 (t, J=7.4Hz, 16H), 1.74 (s, 3H), 1.68 (s, 3H), 1.62 (s, 3H), 1.60 (s, 21H).

[0270] Example 51

[0271]

[0272] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 61 mg (0.5 mmol, 1 equivalent) of 2-methyl-p-benzoquinone, 6.3 mg (0.025 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 87 mg (0.83 mmol, 1.66 equivalent) of 1-chloro-3-methyl-2-butene (isopentene chloride), and 11.9 mg (0.075 mmol, 0.15 equivalent) of 2-methyl-2-nonanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) to the reaction flask. Then connect an air condenser to the round-bottom flask, purging with nitrogen and continuously bubbling nitrogen into the reaction system. Heat the flask to 80°C and stir the reaction for 24 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography with a petroleum ether:ethyl acetate mixture to obtain 74.2 mg of 2-methyl-6-(3-methyl-2-buten-1-yl)-p-benzoquinone, with a yield of 78%. The product was a yellow oily liquid. 1 H-NMR (500MHz, CDCl3) δ (ppm) 6.59 (q, J=1.7Hz, 2H), 5.18-5.11 (m, 1H), 3.10 (d, J=7.6Hz, 2H), 2.03 (d, J=1.6Hz, 3H), 1.76 (s, 3H), 1.63 (s, 3H).

[0273] Example 52

[0274]

[0275] In a dry 10 mL flask, a magnetic stir bar, 69 mg (0.5 mmol, 1 equivalent) of 2-methoxy-p-benzoquinone, 6.3 mg (0.025 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 87 mg (0.83 mmol, 1.66 equivalent) of 1-chloro-3-methyl-2-butene (isoprene chloride), and 23.8 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol were added sequentially. After the solids dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen through the reaction system. The flask was heated to 80°C and the reaction was stirred for 36 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography with a petroleum ether:ethyl acetate mixture to obtain 70.1 mg of 2-methoxy-5-(3-methyl-2-buten-1-yl)-p-benzoquinone, with a yield of 68%. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 6.47 (d, J=1.9Hz, 1H), 5.14 (tt, J=7.1, 1.6Hz, 1H), 3.82 (s, 3H), 3.13 (d, J=7.3Hz, 2H), 1.78-1.74 (m, 3H), 1.63 (s, 3H).

[0276] Example 53

[0277]

[0278] In a dry 10 mL flask, add sequentially the following: a magnetic stir bar, 87 mg (0.5 mmol, 1 equivalent) of 5-hydroxy-1,4-naphthoquinone, 6.3 mg (0.025 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 87 mg (0.83 mmol, 1.66 equivalent) of 1-chloro-3-methyl-2-butene (isoprene chloride), and 1.9 mg (0.025 mmol, 0.05 equivalent) of tert-butanol. After the solids dissolve, add 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) to the reaction flask. Then connect an air condenser to the round-bottom flask to purge nitrogen and continuously bubble nitrogen through the reaction system. Heat the flask to 80°C and stir the reaction for 48 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 49.7 mg of 5-hydroxy-2-(3-methyl-2-buten-1-yl)-1,4-naphthoquinone, with a yield of 41%. The product was a yellow oily liquid. 1 H-NMR (400MHz, CDCl3) δ (ppm) 12.08 (s, 1H), 7.60 (d, J = 2.7Hz, 1H), 7.24 (d, J = 4.1Hz, 2H), 6.7 3 (dt, J=6.0, 1.8Hz, 1H), 5.27-5.16 (m, 1H), 3.26 (d, J=7.3Hz, 2H), 1.79 (s, 3H), 1.67 (s, 3H).

[0279] Example 54

[0280]

[0281] In a dry 10 mL flask, a magnetic stir bar, 54 mg (0.5 mmol, 1 equivalent) of 1,4-p-benzoquinone, 6.3 mg (0.025 mmol, 0.05 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry chlorobenzene, 87 mg (0.83 mmol, 1.66 equivalent) of 1-chloro-3-methyl-2-butene (isopentene chloride), and 11.9 mg (0.075 mmol, 0.15 equivalent) of 2-methyl-2-nonanol were added sequentially. After the solids dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen through the reaction system. The flask was heated to 80°C and the reaction was stirred for 36 hours. The reaction mixture was then centrifuged in a centrifuge tube at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 50.2 mg of 2-(3-methyl-2-buten-1-yl)-p-benzoquinone, with a yield of 57%. The product was a yellow oily liquid. 1 H-NMR (500MHz, CDCl3) δ (ppm) 6.76 (d, J = 10.1Hz, 1H), 6.70 (dd, J = 10.1, 2.5Hz, 1H), 6.53 ( dd, J=4.1, 1.8Hz, 1H), 5.19-5.10 (m, 1H), 3.11 (d, J=7.3Hz, 2H), 1.76 (s, 3H), 1.63 (s, 3H); 13 C-NMR (126MHz, CDCl3) δ (ppm) 188.11, 187.73, 148.66, 136.87, 136.68, 136.43, 132.44, 117.89, 27.59, 25.88, 17.90.

[0282] Example 55

[0283]

[0284] In a dry 10 mL flask, add in sequence the following ingredients: a magnetic stir bar, 91 mg (0.5 mmol, 1 equivalent) of 2,3-dimethoxy-5-methyl-p-benzoquinone, 12.6 mg (0.05 mmol, 0.1 equivalent) of 2,6-dimethyl-3,5-di(ethoxyacyl)-1,4-dihydropyridine, 2.5 mL of dry o-dichlorobenzene, 179 mg (0.25 mmol, 0.5 equivalent) of E-1-chloro-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetradecadeene, and 23.8 mg (0.15 mmol, 0.3 equivalent) of 2-methyl-2-nonanol. After the solid dissolved, 40 mg of a commercially available 60% sodium hydride-mineral oil mixture (containing approximately 24 mg of sodium hydride, 2 equivalents) was added to the reaction flask. An air condenser was then connected to the round-bottom flask to purge nitrogen gas and continuously bubble nitrogen into the reaction system. The flask was heated to 100°C and the reaction was stirred for 42 hours. Afterward, the reaction mixture was centrifuged at 10,000 rpm for 2 minutes. The supernatant was collected and subjected to column chromatography using a petroleum ether:ethyl acetate mixture to obtain 102 mg of coenzyme Q10 (CoQ10), in 47% yield (based on 1-chloro-decamethyl-tetradecadene). The solid was orange. 1 H-NMR (400MHz, CDCl3) δ (ppm) 1.55 (s, 3H), 1.60 (s, 21H), 1.68(s, 6H), 1.74(s, 3H), 1.93-2.02(m, 18H), 2.01(s, 3H), 2.02-2.13(m, 18H), 3.18(d, J=7.2Hz, 2H ), 3.98 (s, 3H), 3.99 (s, 3H), 4.94 (t, J = 7.1Hz, 1H), 5.06 (t, J = 6.8Hz, 1H), 5.12 (t, J = 6.8Hz, 8H) ppm.

Claims

1. A method for preparing a quinone compound as shown in formula I, comprising the following steps: condensing a compound as shown in formula II and a compound as shown in formula III in the presence of a base to obtain the quinone compound as shown in formula I; wherein the condensation is carried out in the presence of an initiator or a reducing agent, and the base is stronger than sodium phenoxide; wherein X is chlorine, bromine or iodine; wherein the reducing agent is a reducing agent for reducing quinone compounds; wherein the definitions of the groups in the method are as follows: wherein X is chlorine, bromine or iodine; wherein the definitions of the groups in the method are as follows: wherein X is chlorine, bromine or iodine; wherein the definitions of the groups in the method are as follows: wherein X is chlorine, bromine or iodine; wherein the definitions of the groups in the method are as follows: wherein X is chlorine, bromine or iodine; wherein the definitions of the groups in the method are as follows: wherein the compound as shown in formula II is 1,4-benzoquinone, 2-methyl-1,4-benzoquinone, 2,3-dimethyl-1,4-benzoquinone, 2,3,5-trimethyl-1,4-benzoquinone, 2,3-dimethoxy-5-methyl-1,4-benzoquinone, 2-methyl-1,4-naphthoquinone or 5-hydroxy-1,4-naphthoquinone; wherein the definitions of the groups in the method are as follows: wherein the definitions of the groups in the method are as follows: wherein X is chlorine or bromine; wherein the compound as shown in formula I is as follows: wherein the condensation is carried out in the presence of a protective gas; wherein the condensation is carried out in an organic solvent or without solvent; wherein the molar ratio of the base to the compound as shown in formula II is (2-4):1; wherein the molar ratio of the compound as shown in formula III to the compound as shown in formula II is (0.1-2.0):1; wherein the condensation is carried out at a temperature of 35°C-100°C; wherein the condensation is carried out for a time period of 0.1 hour-336 hours; wherein the post-treatment of the condensation comprises the following steps: removing the solid and column chromatography; wherein the protective gas is an inert gas; wherein the base is stronger than sodium phenoxide in the organic solvent; wherein the organic solvent is a non-polar organic solvent; wherein the molar volume ratio of the compound as shown in formula II to the organic solvent is 0.1 mol / L-0.3 mol / L; wherein the molar ratio of the base to the compound as shown in formula II is 2:1, 2.5:1 or 4:

1. ； wherein, R 1 is hydrogen, CrC 10 alkyl, C2-C 10 alkenyl or CrC 10 alkoxy; R 2 is hydrogen, CrC 10 alkyl, C2-C 10 alkenyl or CrC 10 alkoxy; R 3 Hydrogen, C1~C 10 Alkyl groups, C2~C 10 alkenyl or C1~C 10 alkoxy groups; or R 2 , R 3 and together with the carbon atom to which they are attached form a C6-C 10 aryl group, a C6-C 10 aryl group substituted with one or more hydroxyl groups, or a 5-10 membered heteroaryl group; the heteroatoms in said heteroaryl group being selected from one or more of N, O, and S, the number of heteroatoms being 1, 2, or 3; R 4 is O; R 5 is O; R 6 For C3~C 100 alkenyl group, by one or more R 6-1 Replacement of C3~C 100 alkenyl, or, C3~C 10 Cycloalkenyl groups; R 6-1 Independently C6~C 10 The aryl group, or a 5-10 member heteroaryl group; the heteroatom in the heteroaryl group is selected from one or more of N, O and S, and the number of heteroatoms is 1, 2 or 3; ​ the anion of the base is hydride, hydroxide or ; R x is C1-C 15 alkyl, C3-C 10 cycloalkyl, or C1-C5 alkyl substituted by one or more R x-1 ; R x-1 is independently hydroxyl, or C3-C 10 cycloalkenyl substituted by one or more C1-C3 alkyl; the cation of the base is an alkali metal ion or an alkaline earth metal ion; The initiator is ; R 1-II is hydrogen, C1-C 10 alkyl, C2-C 10 alkenyl or C1-C 10 alkoxy; R 2-II is hydrogen, C1-C 10 alkyl, C2-C 10 alkenyl or C1-C 10 alkoxy; R 3-II is hydrogen, C1-C 10 alkyl, C2-C 10 alkenyl or C1-C 10 alkoxy; or R 2-II , R 3-II and the carbon atom to which they are attached form a C6-C 10 aryl group, a C6-C 10 aryl group substituted by one or more hydroxy groups, or a 5- to 10-membered heteroaryl group; the heteroatoms in the heteroaryl group being selected from one or more of N, O and S, the number of heteroatoms being 1, 2 or 3; R 4-II is O; R 5-II is O; ​ 2. The method of claim 1, wherein the quinone compound of formula I is prepared by the method comprising: ###0002### formula I R 1 is hydrogen, C1-C4alkyl or C1-C4alkoxy; n is 0, 1 or 2; and 10 R1is hydrogen, C1-C4alkyl or C1-C4alkoxy; n is 0, 1 or 2; and 10 R1is hydrogen, C1 and / or, R 2 is hydrogen, CrC 10 alkyl, C2-C 10 alkenyl or CrC 10 alkoxy; R 3 is hydrogen, CrC 10 alkyl, C2-C 10 alkenyl or CrC 10 alkoxy; or, R 2 , R 3 together with the carbon atom to which they are attached form a C6-C 10 aryl group, or a C6-C 10 aryl group substituted by one or more hydroxyl groups; And / or, R 6 For C3~C 100 The alkenyl group.

3. The method for preparing quinone compounds as shown in Formula I according to claim 2, characterized in that, R 2 Hydrogen, C1~C 10 Alkyl or C1~C 10 alkoxy group; R 3 Hydrogen, C1~C 10 Alkyl or C1~C 10 alkoxy groups; or, R 2 R 3 Together with the carbon atoms attached to it, they form C6~C. 10 aryl group, or C6~C substituted with one or more hydroxyl groups 10 Aryl groups.

4. The method of claim 3, wherein the quinone compound of formula I is prepared by the method comprising: ###0002### formula I R 2 is hydrogen, C1-C4alkyl or C1-C4alkoxy; R 3 is hydrogen, C1-C4alkyl or C1-C4alkoxy; or, R 2 , R 3 and the carbon atom to which they are attached together form phenyl, or phenyl substituted by one or more hydroxy groups.

5. The method of claim 1, wherein the quinone compound of Formula I is prepared by the method comprising: ###0002### Formula I ​ R 1 is hydrogen, CrC 10 alkyl, C2-C 10 alkenyl or CrC 10 alkoxy; R 2 is hydrogen, CrC 10 alkyl, C2-C 10 alkenyl or CrC 10 alkoxy; R 3 Hydrogen, C1~C 10 Alkyl groups, C2~C 10 alkenyl or C1~C 10 alkoxy groups; or R 2 , R 3 and together with the carbon atom to which they are attached form a C6-Ci0aryl group, or a C6-Ci0aryl group substituted by one or more hydroxyl groups; 10 or R 10 and together with the carbon atom to which they are attached form a C6-Ci0aryl group, or a C6-Ci0aryl group substituted by one or more hydroxyl groups; R 4 is O; R 5 is O; R 6 For C3~C 100 alkenyl group, by one or more R 6-1 Replacement of C3~C 100 alkenyl, or, C3~C 10 Cycloalkenyl groups; R 6-1 independently C6-Ci2aryl; and 10 independently C6-Ci2aryl; and ​ 6. The method of claim 1, wherein the quinone compound of Formula I is prepared by the method comprising: ###0002### Formula I ​ R 1 is hydrogen, C1-C4alkyl or C1-C4alkoxy; n is 0, 1 or 2; and 10 R1is hydrogen, C1-C4alkyl or C1-C4alkoxy; n is 0, 1 or 2; and 10 R1is hydrogen, C1 R 2 is hydrogen, C1-C4alkyl or C1-C4alkoxy; n is 0, 1 or 2; and 10 R1is hydrogen, C1-C4alkyl or C1-C4alkoxy; n is 0, 1 or 2; and 10 R1is hydrogen, C1 R 3 Hydrogen, C1~C 10 Alkyl or C1~C 10 alkoxy groups; or R 2 , R 3 and together with the carbon atom to which they are attached form a C6-C10aryl group, or a C6-C10aryl group substituted by one or more hydroxyl groups; 10 or R 10 and together with the carbon atom to which they are attached form a C6-C10aryl group, or a C6-C10aryl group substituted by one or more hydroxyl groups; R 4 is O; R 5 is O; R 6 is C3-C6alkenyl; and 100 C3-C6alkenyl; and ​ 7. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, ​ R 1 is hydrogen, C1-C4alkyl or C1-C4alkoxy; R 2 is hydrogen, C1-C4alkyl or C1-C4alkoxy; R 3 is hydrogen, C1-C4alkyl or C1-C4alkoxy; or R 2 , R 3 and the carbon atoms to which they are attached form a phenyl group, or a phenyl group substituted by one or more hydroxyl groups; R 4 is O; R 5 is O; R 6 is a chlorophyll radical or n is 0 to 9; ​ 8. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, ​ ​ R 6 is 3-methyl-2-buten-1-yl, (all-E)-3,7-dimethyl-2,6-octadien-1-yl, (all-E)-3,7,11- trimethyl-2,6,10-dodecatrien-1-yl, phytyl, (all-E)-3,7,11,15-tetramethyl-2,6,10,14- hexadecatetraen-1-yl, (all-E)-3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26- octacosheptaen-1-yl, (all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30, 34-hexatriacontanon-1-yl, or (all-E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38- tetracontadecaen-1-yl.

9. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, ​ ​ The compound as shown in Formula II is 2,3-dimethoxy-5-methyl-1,4-benzoquinone; R 6 is , n is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; ​ The compound as shown in Formula II is 2-methyl-1,4-naphthoquinone; R 6 is , n is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

10. The method for preparing the quinone compound as shown in Formula I according to claim 1, characterized in that, when R 1 is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4alkyl; and / or, when R 1 is C2-C 10 alkenyl, said C2-C 10 alkenyl is C2-C5 alkenyl; And / or, when R 1 C1~C 10 When the alkoxy group is present, the C1~C 10 The alkoxy group is a C1~C4 alkoxy group; and / or, when R 2 is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4alkyl; and / or, when R 2 is C2-C 10 alkenyl, said C2-C 10 alkenyl is C2-C5 alkenyl; and / or, when R 2 is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4alkyl; and / or, when R 3 is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4 alkyl; and / or, when R 3 is C2-C 10 alkenyl, said C2-C 10 alkenyl is C2-C5 alkenyl; And / or, when R 3 C1~C 10 When the alkoxy group is present, the C1~C 10 The alkoxy group is a C1~C4 alkoxy group; and / or, when R 2 , R 3 and the carbon atom to which they are attached form a C6-C 10 aryl group, said C6-C 10 aryl group is phenyl; And / or, when R 2 R 3 Together with the carbon atom attached thereto, they form C6~C atoms that are substituted with one or more hydroxyl groups. 10 When the aryl group is present, the C6~C 10 The aryl group is phenyl; and / or, when R 6 is C3-C 100 alkenyl, the beta and gamma positions of X together form a double bond; and / or, when R 6 is C3-C 100 alkenyl, said C3-C 100 alkenyl contains 1-15 double bonds; And / or, when R 6 For one or more R 6-1 Replacement of C3~C 100 When the β-position and β-position of X are both double bonds; And / or, when R 6 For one or more R 6-1 Replacement of C3~C 100 When the alkenyl group is present, the C3~C 100 The alkenyl group contains 1 to 15 double bonds; and / or, when R 6 is C3-C 6-1 substituted with multiple R 100 , said multiple is 2 or 3; And / or, when R 6-1 Independently C6~C 10 When the aryl group is present, the C6~C 10 The aryl group is phenyl; and / or, when R 6 is C3-C 10 cycloalkenyl, the beta and gamma positions of X together form a double bond; and / or, when R 6 is C3-C 10 cycloalkenyl, said C3-C 10 cycloalkenyl contains 1 to 5 double bonds; and / or, when R 6 is C3-C 10 cycloalkenyl, said C3-C 10 cycloalkenyl is C3-C6cycloalkenyl; ​ 11. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, when R 1 is C1-C 10 alkyl, said C1-C 10 alkyl is methyl; and / or, when R 1 is C2-C 10 alkenyl, said C2-C 10 alkenyl is 3-methyl-2-buten-1-yl; and / or, when R 1 is C1-C 10 alkyl, said C1-C 10 alkyl is methyl; and / or, when R 1 is C1-C 10 alkoxy, said C1-C 10 alkoxy is methoxy; and / or, when R 2 is C1-C 10 alkyl, said C1-C 10 alkyl is methyl; and / or, when R 2 is C2-C 10 alkenyl, said C2-C 10 alkenyl is 3-methyl-2-buten-1-yl; And / or, when R 2 C1~C 10 When the alkoxy group is present, the C1~C 10 The alkoxy group is a methoxy group; and / or, when R 3 is C1-C 10 alkyl, said C1-C 10 alkyl is methyl; and / or, when R 3 is C2-C 10 alkenyl, said C2-C 10 alkenyl is 3-methyl-2-buten-1-yl; and / or, when R 3 is C1-C 10 alkyl, said C1-C 10 alkyl is methyl; and / or, when R 3 is C1-C 10 alkoxy, said C1-C 10 alkoxy is methoxy; and / or, when R 6 is C3-C 100 alkenyl, said C3-C 100 alkenyl contains 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 double bonds; and / or, when R 6 is C3-C 100 alkenyl, said C3-C 100 alkenyl is C5-C 100 terpenyl; And / or, when R 6 For one or more R 6-1 Replacement of C3~C 100 When the alkenyl group is present, the C3~C 100 The alkenyl group contains 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 double bonds; and / or, when R 6 is C3-C6alkenyl substituted by one or more R 6-1 , said C3-C6alkenyl is C5-C6alkenyl; 100 ; and / or, when R 100 is C3-C6alkenyl substituted by one or more R 100 , said C3-C6alkenyl is C5-C6alkenyl; and / or, when R 6 is C3-C 10 cycloalkenyl, said C3-C 10 cycloalkenyl contains 1, 2, 3, 4 or 5 double bonds.

12. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, when R is C3-C7cycloalkenyl, said C3-C7cycloalkenyl is 6 C3-C7cycloalkyl, 10 C3-C7cycloalkenyl, 10 C3-C7cycloalkyl, C3-C7cycloalkyl.

13. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, when R 6 is C3-C 100 alkenyl, said C3-C 100 alkenyl is n is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, or 19; and / or, when R 6 is C3-C 6-1 alkenyl substituted by one or more R 100 , said C3-C 100 alkenyl is n is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 or 19.

14. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, When R 6 For being an R 6-1 Replacement of C3~C 100 When the alkenyl group is present, it is subjected to an R 6-1 Replacement of C3~C 100 The alkenyl group is 3-phenyl-2-propen-1-yl.

15. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, ​ , , , , , , , , , , , , , , , , , , , , , and .

16. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, ​ ​ ​ ​ ​ ​ ​ 17. The method for preparing a quinone compound as shown in Formula I as described in claim 16, characterized in that, ​ ​ ​ ​ ​ and / or, when the condensation reaction is carried out in the presence of an initiator, the molar ratio of the initiator to the compound of Formula II is 0.01:1, 0.025:1, 0.05:1, 0.075:1, 0.10:1, 0.15:1, 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, or 0.8:1; and / or, when said condensation reaction is carried out in the presence of a reducing agent, said reducing agent is , or , R 7-1 and R 7-2 are independently C1-C4 alkyl; and / or, when the condensation reaction is carried out in the presence of a reducing agent, the molar ratio of the reducing agent to the compound of Formula II is 0.01:1, 0.025:1, 0.05:1, 0.075:1, 0.10:1, 0.15:1, 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, or 0.8:1; and / or, the molar ratio of the compound of Formula III to the compound of Formula II is 0.2:1, 0.4:1, 0.5:1, 1:1, 1.05:1, 1.65:1, or 1.70:1; and / or, the temperature of the condensation reaction is 50°C, 60°C, 65°C, 70°C, 75°C, 80°C, 85°C, 90°C, or 95°C; and / or, the post-treatment of the condensation reaction comprises the following steps: removing the solid, and column chromatography; the method of removing the solid is centrifugation or filtration.

18. The method for preparing a quinone compound as shown in Formula I according to claim 17, characterized in that, When the condensation reaction is carried out in the presence of a protective gas, the protective gas is nitrogen; and / or, when the condensation reaction is carried out in an organic solvent, the organic solvent is a halogenated hydrocarbon solvent and / or a hydrocarbon solvent; and / or, when the condensation reaction is carried out in an organic solvent, the molar volume ratio of the compound of Formula II to the organic solvent is 0.1 mol / L ~ 0.2 mol / L; and / or, when said condensation reaction is carried out in the presence of a reducing agent, said reducing agent is , , or .

19. The method for preparing a quinone compound as shown in Formula I as described in claim 18, characterized in that, When the condensation reaction is carried out in an organic solvent, the organic solvent comprises a halogenated hydrocarbon solvent, the halogenated hydrocarbon solvent is a halogenated alkane solvent and / or a halogenated aromatic hydrocarbon solvent; and / or, when the condensation reaction is carried out in an organic solvent, the organic solvent comprises a hydrocarbon solvent, the hydrocarbon solvent is an alkane solvent and / or an aromatic hydrocarbon solvent.

20. The method for preparing a quinone compound as shown in Formula I according to claim 19, characterized in that, When the condensation reaction is carried out in an organic solvent, the organic solvent comprises a halogenated hydrocarbon solvent, the halogenated hydrocarbon solvent comprises a halogenated alkane solvent, the halogenated alkane solvent is dichloromethane and / or 1,2-dichloroethane; and / or, when the condensation reaction is carried out in an organic solvent, the organic solvent comprises a halogenated hydrocarbon solvent, the halogenated hydrocarbon solvent comprises a halogenated aromatic hydrocarbon solvent, the halogenated aromatic hydrocarbon solvent is one or more of fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, trifluoromethylbenzene, o-dichlorobenzene, m-dichlorobenzene, and p-dichlorobenzene; and / or, when the condensation reaction is carried out in an organic solvent, the organic solvent comprises a hydrocarbon solvent, the hydrocarbon solvent comprises an alkane solvent, the alkane solvent is mineral oil; and / or, when the condensation reaction is carried out in an organic solvent, the organic solvent comprises a hydrocarbon solvent, the hydrocarbon solvent comprises an aromatic hydrocarbon solvent, the aromatic hydrocarbon solvent is one or more of benzene, toluene, o-xylene, p-xylene, m-xylene and mesitylene.

21. The method for preparing a quinone compound as shown in Formula I according to claim 20, characterized in that, and / or, when the condensation reaction is carried out in an organic solvent, the organic solvent comprises a halogenated hydrocarbon solvent, the halogenated hydrocarbon solvent comprises a halogenated aromatic hydrocarbon solvent, the halogenated aromatic hydrocarbon solvent is chlorobenzene or o-dichlorobenzene; and / or, when the condensation reaction is carried out in an organic solvent, the organic solvent comprises a hydrocarbon solvent, the hydrocarbon solvent comprises an aromatic hydrocarbon solvent, the aromatic hydrocarbon solvent is toluene.

22. The method for preparing a quinone compound as shown in Formula I as described in claim 16, characterized in that, The anion of the base is hydroxide or ; R x is C1-C 15 alkyl.

23. The method for preparing a quinone compound as shown in Formula I as described in claim 16, characterized in that, when R x is C1-C 15 alkyl, said C1-C 15 alkyl is methyl, ethyl, isopropyl, , or , R x-2 is C1-C 12 alkyl; and / or, when R x is C3-C 10 cycloalkyl, said C3-C 10 cycloalkyl is bridged C5-C 10 cycloalkyl; and / or, when R x is C1-C5 alkyl substituted with one or more R x-1 the number of said groups is 2, 3 or 4; and / or, when R x-1 independently C3-C6cycloalkyl or C3-C6cycloalkenyl, wherein said C3-C6cycloalkyl or C3-C6cycloalkenyl is independently substituted with one or more C1-C3alkyl; 10 independently C3-C6cycloalkyl or C3-C6cycloalkenyl, wherein said C3-C6cycloalkyl or C3-C6cycloalkenyl is independently substituted with one or more C and / or, when R x-1 independently C3-C6cycloalkyl, C3-C6cycloalkenyl, or C4-C8cycloalkadienyl, each of which is optionally substituted with one or more C1-C3alkyl; 10 independently C3-C6cycloalkyl, C3-C6cycloalkenyl, or C4-C8cycloalkadienyl, each of which is optionally substituted with one or more C1-C3alkyl; 10 independently C3-C6cycloalkyl, C3-C6cycloalkenyl, or C4-C8cycloalk and / or, when R x is C1-C5 alkyl substituted by one or more R x-1 , said C1-C5 alkyl is n-propyl, i-propyl or neopentyl; and / or, when the cation of the base is an alkali metal ion, the alkali metal ion is lithium ion, sodium ion or potassium ion; and / or, when the cation of the base is an alkaline earth metal ion, the alkaline earth metal ion is magnesium ion or calcium ion.

24. The method for preparing a quinone compound as shown in Formula I as described in claim 23, characterized in that, Inside, and The bonded carbon atom is a tertiary carbon atom; and / or, when the alkyl group of C1-C 15 is R x-2 is a C1-C 12 straight chain alkyl group; and / or, when R x is C3-C 10 cycloalkyl, said C3-C 10 cycloalkyl is adamantyl; and / or, when R x-1 independently is C3-C6cycloalkyl substituted with one or more C1-C3alkyl; 10 independently is C3-C6cycloalkyl substituted with one or more C1-C3alkyl; 10 independently is C3-C6cycloalkyl substituted with one or more C1-C3alkyl; .

25. The method for preparing a quinone compound as shown in Formula I as described in claim 24, characterized in that, when the alkyl group of C1-C7alkyl is 15 C1-C7alkyl R x-2 is C1-C7straight chain alkyl; and / or, when R x is C3-C 10 cycloalkyl, said C3-C 10 cycloalkyl is .

26. The method for preparing a quinone compound as shown in Formula I according to claim 23, characterized in that, When C1~C 15 The alkyl group is At that time, the For tert-butyl, , or .

27. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, The base is selected from one or more of the group consisting of alkali metal hydride, alkali metal hydroxide, and alkali metal salt.

28. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, The base is selected from one or more of the group consisting of sodium hydride, sodium hydroxide, sodium salts and potassium salts.

29. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, The base is selected from one or more of the group consisting of sodium hydroxide, sodium salts and potassium salts.

30. The method for preparing a quinone compound as shown in Formula I as described in claim 28 or 29, characterized in that, when the base comprises sodium hydroxide, the sodium hydroxide is generated in situ from water and sodium hydride; And / or, when the alkali contains When sodium salt is used, the aforementioned The sodium salt is sodium methoxide, sodium 2-methyl-2-nonoxide, sodium tert-butoxide, sodium 1-adamantoxide, sodium isopropoxide, sodium ethoxide, sodium terpineol, sodium 3-ethyl-3-pentanol, sodium 2-methyl-2-hexanol, sodium 1,3-propanediol, sodium glycerol, sodium pentaerythritol, or sodium 2-methyl-2-pentanol. And / or, when the alkali contains When potassium salts are used, the aforementioned The potassium salts are potassium methoxide, potassium 2-methyl-2-nonoxide, potassium tert-butoxide, potassium 1-adamantoxide, potassium isopropoxide, potassium ethoxide, potassium terpineol, potassium 3-ethyl-3-pentanol, potassium 2-methyl-2-hexanol, potassium 1,3-propanediol, potassium glycerol, potassium pentaerythritol, or potassium 2-methyl-2-pentanol. and / or, when said base comprises sodium salt, said sodium salt is generated in situ with sodium hydride; and / or, when the base comprises potassium salt, said potassium salt is generated in situ with potassium hydride.

31. The method for preparing a quinone compound as shown in Formula I according to claim 30, characterized in that, when the base comprises sodium hydroxide, the sodium hydroxide is generated in situ from water and sodium hydride, the amount of water is catalytic amount, and the molar amount of sodium hydride is the same as the molar amount of the base; and / or, when said base comprises sodium salt, said sodium salt is formed in situ from said sodium hydride is formed in situ from said sodium hydride is present in catalytic amounts, the molar amount of said sodium hydride being the same as the molar amount of said base.

32. The method for preparing quinone compounds as shown in Formula I according to claim 31, characterized in that, when the amount of water is catalytic amount, the catalytic amount refers to that the molar ratio of water to the compound as shown in formula II is (0.08~0.15):1; and / or, when the amount of said catalytic amount means that the amount of said molar ratio of the compound of formula II is (0.03~0.3):

1.

33. The method for preparing quinone compounds as shown in Formula I according to claim 32, characterized in that, when the amount of water is catalytic amount, the catalytic amount refers to that the molar ratio of water to the compound as shown in formula II is 0.10:1; and / or, when the amount of said catalytic amount means that the amount of said molar ratio of the compound of Formula II is 0.03:1, 0.05:1, 0.06:1, 0.07:1, 0.123:1, 0.125:1, 0.165:1, 0.25:1, or 0.3:

1.

34. The method for preparing a quinone compound as shown in Formula I as described in claim 16, characterized in that, when R 1-II is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4alkyl; and / or, when R 1-II is C2-C 10 alkenyl, said C2-C 10 alkenyl is C2-C5 alkenyl; and / or, when R 1-II is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4alkyl; and / or, when R 2-II is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4 alkyl; and / or, when R 2-II is C2-C 10 alkenyl, said C2-C 10 alkenyl is C2-C5 alkenyl; and / or, when R 2-II is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4alkyl; and / or, when R 3-II is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4 alkyl; and / or, when R 3-II is C2-C 10 alkenyl, said C2-C 10 alkenyl is C2-C5 alkenyl; and / or, when R 3-II is C1-C 10 alkyl, said C1-C 10 alkyl is C1-C4alkyl; and / or, when R 2-II , R 3-II and the carbon atom to which they are attached form a C6-C 10 aryl group, said C6-C 10 aryl group is phenyl; And / or, when R 2-II R 3-II Together with the carbon atom attached thereto, they form C6~C atoms that are substituted with one or more hydroxyl groups. 10 When the aryl group is present, the C6~C 10 The aryl group is phenyl; and / or, said R 1-II is the same as said R 1 ; said R 2-II is the same as said R 2 ; said R 3-II is the same as said R 3 .

35. The method for preparing a quinone compound as shown in Formula I as described in claim 34, characterized in that, when R 1-II is C1-C 10 alkyl, said C1-C 10 alkyl is methyl; and / or, when R 1-II is C2-C 10 alkenyl, said C2-C 10 alkenyl is 3-methyl-2-buten-1-yl; And / or, when R 1-II C1~C 10 When the alkoxy group is present, the C1~C 10 The alkoxy group is a methoxy group; and / or, when R 2-II is C1-C 10 alkyl, said C1-C 10 alkyl is methyl; and / or, when R 2-II is C2-C 10 alkenyl, said C2-C 10 alkenyl is 3-methyl-2-buten-1-yl; and / or, when R 2-II is C1-C 10 alkyl, said C1-C 10 alkyl is methyl; and / or, when R 2-II is C1-C 10 alkoxy, said C1-C 10 alkoxy is methoxy. and / or, when R 3-II is C1-C 10 alkyl, said C1-C 10 alkyl is methyl; and / or, when R 3-II is C2-C 10 alkenyl, said C2-C 10 alkenyl is 3-methyl-2-buten-1-yl; and / or, when R 3-II is C1-C 10 alkyl, said C1-C 10 alkyl is methyl.

36. The method for preparing a quinone compound as shown in Formula I as described in claim 35, characterized in that, The is 1,4-hydroquinone.

37. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, the condensation reaction has the following reaction parameters: The condensation reaction is carried out in the presence of a protective gas; the condensation reaction is carried out in an organic solvent, the organic solvent is a halogenated aromatic hydrocarbon solvent, the molar volume ratio of the compound as shown in formula II to the organic solvent is 0.1 mol / L ~ 0.3 mol / L; the base is sodium hydroxide or sodium salt, R x is , R x-2 is a linear alkyl group with 1 to 7 carbon atoms, the molar ratio of the base to the compound as shown in formula II is (2 to 4):1; the condensation reaction is carried out in the presence of , R 7-1 and R 7-2 are independently alkyl groups with 1 to 4 carbon atoms, the molar ratio of the to the compound as shown in formula II is (0.025 to 0.10):1; the molar ratio of the compound as shown in formula III to the compound as shown in formula II is (0.2 to 2.0):1; the temperature of the condensation reaction is 40°C to 100°C.

38. The method for preparing quinone compounds as shown in Formula I according to claim 1, characterized in that, the condensation reaction has the following reaction parameters: Scheme B: The condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or ortho-dichlorobenzene, the molar volume ratio of the compound as shown in formula II to the chlorobenzene or ortho-dichlorobenzene is 0.1 mol / L ~ 0.2 mol / L; the base is sodium salt, R x is tert-butyl, , or , the molar ratio of the base to the compound as shown in formula II is (2 ~ 2.5): 1; the condensation reaction is carried out in the presence of , the molar ratio of the to the compound as shown in formula II is (0.05 ~ 0.10): 1; the molar ratio of the compound as shown in formula III to the compound as shown in formula II is (0.2 ~ 1.70): 1; the temperature of the condensation reaction is 70°C ~ 80°C; Scheme C: The condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or o-dichlorobenzene, the molar volume ratio of the compound as shown in formula II to the chlorobenzene or o-dichlorobenzene is 0.1 mol / L-0.2 mol / L; the base is sodium hydride and sodium salt, R x is , is tert-butyl, , or , the molar ratio of the base to the compound as shown in formula II is (2-2.5):1; the condensation reaction is further carried out in the presence of , the molar ratio of the to the compound as shown in formula II is (0.05-0.10):1; the molar ratio of the compound as shown in formula III to the compound as shown in formula II is (0.2-1.70):1; the temperature of the condensation reaction is 70°C-80°C; Scheme D: The condensation reaction is carried out in the presence of nitrogen; the condensation reaction is carried out in chlorobenzene or o-dichlorobenzene, and the molar volume ratio of the compound of formula II to the chlorobenzene or o-dichlorobenzene is 0.1 mol / L ~ 0.2 mol / L; the base is sodium hydride and R x for , For tert-butyl, , or The molar ratio of the base to the compound shown in Formula II is (2~2.5):

1. The molar ratio of the compound to that shown in Formula II is (0.03~0.3):1; the condensation reaction is still ongoing. The above is carried out in the presence of the present, The molar ratio of the compound shown in Formula II to the compound shown in Formula III is (0.05~0.10):1; the molar ratio of the compound shown in Formula III to the compound shown in Formula II is (0.2~1.70):1; the temperature of the condensation reaction is 70°C~80°C.

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