Organic compound and preparation method thereof, bactericide and purification device

Abstract

The invention relates to an organic compound and a preparation method thereof, a bactericide and a purification device. An organic compound having a general formula (I): # imgabs0 #; wherein L is selected from at least one of a single bond, an alkylene group with 1 to 8 carbon atoms and an alkoxyacyl group with 2 to 8 carbon atoms; r1 and R2 are respectively and independently selected from at least one of hydrogen, substituted or unsubstituted C1-C8 alkyl and substituted or unsubstituted C1-C8 alkyl; or R1 and R2 and the C atom commonly connected with R1 and R2 form a C3-C8 naphthenic base. The organic compound disclosed by the invention contains the amido bond, and the amido bond is connected with an R-configuration carbon atom, so that the organic compound has a bactericidal effect, particularly can effectively inhibit the activity of escherichia coli and staphylococcus aureus, is relatively good in bactericidal stability, and does not generate toxic substances.

Description

Technical Field

[0001] The present application relates to the field of compound technology, and in particular to an organic compound and a preparation method thereof, a bactericide and a purification device. Background Art

[0002] There are a large number of bacteria (including endotoxins), fungi (including fungal spores), viruses and other microorganisms in the air, which usually attach to particles of a certain size, such as dust, droplet nuclei, etc., to form aerosols suspended in the air, which are then transmitted through the air. Air, as an important transmission medium, can cause various poisonings, infections, allergies and infectious diseases. Based on this, people's demand for air sterilization and disinfection has risen sharply. Traditional disinfection methods mainly use the chemical properties of substances such as chlorine and ozone for disinfection, but this method has great disadvantages - it produces a large number of toxic compounds, which are extremely harmful to the environment and human health; and other disinfectants have poor sterilization effects.

[0003] Therefore, it is necessary to improve the traditional technology. Summary of the invention

[0004] Based on this, the present application provides an organic compound with good bactericidal effect and its preparation method, bactericide and purification device.

[0005] The technical solution of this application to solve the above technical problems is as follows.

[0006] An organic compound having the general formula (I):

[0007]

[0008] Wherein, L is selected from a single bond and C 1 ~C 8 At least one of alkylene groups;

[0009] R 1 and R 2 are independently selected from hydrogen, substituted or unsubstituted C 1 ~C 8 Alkyl and C 2 ~C 8 At least one of alkoxyacyl; or, R 1 and R 2 and the C atoms they are connected to form C 3 ~C 8 Cycloalkyl.

[0010] In some embodiments, in the organic compound, the substituted C 1 ~C 8 Substituents in the alkyl group include hydroxyl, substituted or unsubstituted indolyl, substituted or unsubstituted C6 ~C 20 Aromatic and substituted or unsubstituted C 3 ~C 8 At least one of cycloalkyl.

[0011] In some embodiments, in the organic compound, the substituted or unsubstituted indolyl, the substituted or unsubstituted C 6 ~C 20 The aromatic group and the substituted or unsubstituted C 3 ~C 8 Substituents in cycloalkyl groups include C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, hydroxyl, C 7 ~C 16 At least one of an aralkyloxy group, a halogen group and a nitro group.

[0012] In some embodiments, in the organic compound, the substituents in the substituted or unsubstituted indolyl group include C 1 ~C 6 Alkyl and C 2 ~C 6 At least one of alkenyl; and / or

[0013] The substituted or unsubstituted C 6 ~C 20 Substituents in aromatic groups include hydroxyl, C 7 ~C 16 At least one of an aralkyloxy group, a halogen group and a nitro group.

[0014] In some embodiments, in the organic compound, R 1 is hydrogen, R 2 Selected from hydrogen, C 2 Alkoxyacyl or one of the structures of formula (II-1) to (II-10):

[0015]

[0016] Or, R 1 and R 2 Together with the C atom to which they are connected, they form a cyclobutyl group.

[0017] In some embodiments, in the organic compound, L is selected from one of a single bond and an ethylene group.

[0018] In some embodiments, the organic compound is selected from one of the structures of formula (III-1) to (III-12):

[0019]

[0020] Accordingly, a method for preparing an organic compound is provided, comprising the following steps:

[0021] (R)-3-phenyl-2-hydroxypropionic acid and the compound represented by formula (IV) are mixed for condensation reaction to generate the compound represented by formula (I):

[0022]

[0023] Among them, in formula (I) and formula (IV),

[0024] L is selected from a single bond and C 1 ~C 8 At least one of alkylene groups;

[0025] R 1 and R 2 are independently selected from hydrogen, substituted or unsubstituted C 1 ~C 8 Alkyl and C 2 ~C 8 At least one of alkoxyacyl; or, R 1 and R 2 and the C atoms they are connected to form C 3 ~C 8 Cycloalkyl.

[0026] In some embodiments, in the method for preparing an organic compound, the compound represented by formula (IV) includes at least one of the structures of formula (IV-1) to (IV-10):

[0027] .

[0028] In some embodiments, in the method for preparing an organic compound, the condensation reaction is carried out under the action of a catalyst, and the catalyst comprises at least one of HOBT, EDCI and DIPEA; and / or

[0029] The solvent for the condensation reaction included DCM.

[0030] On the one hand, the present application provides the use of the above organic compound or the organic compound prepared by the above preparation method in the preparation of a fungicide.

[0031] On the other hand, the present application provides a fungicide, comprising the above organic compound or the organic compound prepared by the above preparation method.

[0032] The present application also provides a purification product, comprising the above-mentioned bactericide.

[0033] Compared with the prior art, the organic compound of the present application has the following beneficial effects:

[0034] The organic compound of the present application contains an amide bond, and the amide bond is connected to the R-configuration carbon atom, has a bactericidal effect, and can effectively inhibit the activity of Escherichia coli and Staphylococcus aureus, and has good bactericidal stability and does not produce toxic substances. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] In order to more clearly illustrate the specific implementation methods of the present application or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present application. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying any creative work.

[0036] Figure 1 The hydrogen spectrum of the compound represented by formula (III-1) prepared in Example 1;

[0037] Figure 2 The hydrogen spectrum of the compound represented by formula (III-2) prepared in Example 2;

[0038] Figure 3 The hydrogen spectrum of the compound represented by formula (III-3) prepared in Example 3;

[0039] Figure 4 The hydrogen spectrum of the compound represented by formula (III-4) prepared in Example 4;

[0040] Figure 5 The hydrogen spectrum of the compound represented by formula (III-5) prepared in Example 5;

[0041] Figure 6 The hydrogen spectrum of the compound represented by formula (III-6) prepared in Example 6;

[0042] Figure 7 The hydrogen spectrum of the compound represented by formula (III-7) prepared in Example 7;

[0043] Figure 8 This is the hydrogen spectrum of the compound represented by formula (III-8) prepared in Example 8;

[0044] Fig. 9 The hydrogen spectrum of the compound represented by formula (III-9) prepared in Example 9;

[0045] Fig.10 The hydrogen spectrum of the compound represented by formula (III-10) prepared in Example 0;

[0046] Fig.11The hydrogen spectrum of the compound represented by formula (III-11) prepared in Example 11;

[0047] Fig.12 This is the hydrogen spectrum of the compound represented by formula (III-12) prepared in Example 12. DETAILED DESCRIPTION

[0048] References to embodiments of the present application will now be provided in detail, one or more examples of which are described below. Each example is provided as an explanation rather than a limitation of the present application. In fact, it will be apparent to those skilled in the art that various modifications and variations may be made to the present application without departing from the scope or spirit of the present application. For example, a feature described or described as part of one embodiment may be used in another embodiment to produce a further embodiment.

[0049] Therefore, it is intended that the present application covers such modifications and variations that fall within the scope of the appended claims and their equivalents. Other objects, features and aspects of the present application are disclosed in or are apparent from the following detailed description. It will be appreciated by those of ordinary skill in the art that this discussion is merely a description of exemplary embodiments and is not intended to limit the broader aspects of the present application.

[0050] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art to which this application belongs. The terms used herein in the specification of this application are only for the purpose of describing specific embodiments and are not intended to limit this application.

[0051] The term "comprises", "comprising" or any other variant thereof is intended to cover non-exclusive inclusion, so that the process, method, article or equipment including a series of elements includes not only those elements, but also includes other elements not explicitly listed, or also includes elements inherent to such process, method, article or equipment. In the absence of more restrictions, the elements defined by the sentence "comprising one..." do not exclude the presence of other identical elements in the process, method, article or equipment including the elements. The indefinite articles "a kind of" and "one" before the elements or components of the present application are not restrictive to the quantity requirements (i.e., the number of occurrences) of the elements or components. Therefore, "one" or "a kind of" should be interpreted as including one or at least one, and the elements or components in the singular form also include the plural form, unless the number obviously refers only to the singular form. The meaning of "multiple" is at least two, such as two, three, etc., unless otherwise clearly and specifically defined.

[0052] The weight of the relevant components mentioned in the specification of the examples of this application can not only refer to the specific content of each component, but also represent the proportional relationship between the weights of the components. Therefore, as long as the content of the relevant components is proportionally enlarged or reduced according to the specification of the examples of this application, it is within the scope disclosed in the specification of the examples of this application. Specifically, the weight described in the specification of the examples of this application can be mass units known in the chemical industry such as μg, mg, g, and kg.

[0053] Except as shown in the operating examples or otherwise indicated, all numbers used in the specification and claims to indicate the amount of ingredients, physicochemical properties, etc. are understood to be adjusted by the term "about" in all cases. For example, therefore, unless otherwise indicated, the numerical parameters listed in the above specification and the attached claims are approximate values, and those skilled in the art can use the teachings disclosed herein to seek to obtain the desired properties and appropriately change these approximate values. The use of numerical ranges expressed as endpoints includes all numbers within the range and any range within the range, for example, 1 to 5 includes 1, 1.1, 1.3, 1.5, 2, 2.75, 3, 3.80, 4 and 5, etc.

[0054] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent, and adjacent groups may form an aliphatic, aromatic or heteroaromatic ring system with each other.

[0055] In this application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that it is optionally substituted by a group acceptable in the art. Including but not limited to: C 1 ~C 20 Alkyl, heterocyclic group containing 3 to 20 ring atoms, aryl group containing 5 to 20 ring atoms, heteroaryl group containing 5 to 20 ring atoms, silanyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, -NRR', cyano, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, nitro or halogen, and the above groups can also be further substituted by substituents acceptable in the art; it is understandable that R and R' in -NRR' are each independently substituted by groups acceptable in the art, including but not limited to H, C 1 ~C 6 Alkyl, cycloalkyl containing 3 to 8 ring atoms, heterocyclic group containing 3 to 8 ring atoms, aryl containing 5 to 20 ring atoms or heteroaryl containing 5 to 10 ring atoms; C 1 ~C 6The alkyl group, the cycloalkyl group having 3 to 8 ring atoms, the heterocyclic group having 3 to 8 ring atoms, the aryl group having 5 to 20 ring atoms or the heteroaryl group having 5 to 10 ring atoms may be further substituted by one or more of the following groups: 1 ~C 6 Alkyl, cycloalkyl containing 3 to 8 ring atoms, heterocyclic group containing 3 to 8 ring atoms, halogen, hydroxyl, nitro or amino.

[0056] In the present application, the "number of ring atoms" refers to the number of atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0057] Aromatic groups refer to hydrocarbon groups containing at least one aromatic ring. Heteroaromatic groups refer to aromatic hydrocarbon groups containing at least one heteroatom. The heteroatom is preferably selected from Si, N, P, O, S and / or Ge, and is particularly preferably selected from Si, N, P, O and / or S. Condensed ring aromatic groups refer to aromatic groups whose rings may have two or more rings, wherein two carbon atoms are shared by two adjacent rings, i.e., condensed rings. Condensed heterocyclic aromatic groups refer to condensed ring aromatic hydrocarbon groups containing at least one heteroatom. For the purposes of this application, aromatic groups or heteroaromatic groups include not only systems of aromatic rings, but also non-aromatic ring systems. Therefore, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc. are also considered to be aromatic groups or heterocyclic aromatic groups for the purpose of this application. For the purpose of this application, fused aromatic or fused heteroaromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups may be interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N or O atoms). Thus, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc. are also considered fused aromatic ring systems for the purpose of this application.

[0058] Specifically, examples of the fused ring aromatic group include naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, perylene, tetracene, pyrene, benzopyrene, acenaphthene, fluorene, and derivatives thereof.

[0059] Specifically, examples of fused heterocyclic aromatic groups include benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanopyrrole, furanofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary pyridine, quinazoline, quinazolinone, and derivatives thereof.

[0060] In the present application, aromatic group, aromatic group and aromatic ring system have the same meaning and can be interchanged.

[0061] In the present application, heteroaromatic group, heteroaromatic group and heteroaromatic ring system have the same meaning and can be interchanged.

[0062] In the present application, "adjacent groups" means that these groups are bonded to the same carbon atom or to adjacent carbon atoms. These definitions apply correspondingly to "adjacent substituents".

[0063] An embodiment of the present application provides an organic compound having the general formula (I):

[0064]

[0065] Wherein L is selected from a single bond and C 1 ~C 8 At least one of alkylene groups;

[0066] R 1 and R 2 are independently selected from hydrogen, substituted or unsubstituted C 1 ~C 8 Alkyl and C 2 ~C 8 At least one of alkoxyacyl; or, R 1 and R 2 and the C atoms they are connected to form C 3 ~C 8 Cycloalkyl.

[0067] The organic compound of the present application contains an amide bond, and the amide bond is connected to the R-configuration carbon atom, has a bactericidal effect, and can effectively inhibit the activity of Escherichia coli and Staphylococcus aureus, and has good bactericidal stability and does not produce toxic substances.

[0068] C 1 ~C 8 Alkylene refers to a saturated hydrocarbon group containing 1 to 8 carbon atoms, and a divalent group formed by removing a hydrogen atom from each of the two ends of the hydrocarbon group. The following is a detailed introduction:

[0069] C 1 Alkylene: methylene, chemical formula is -CH 2-;

[0070] C 2 Alkylene: 1,2-ethylene, chemical formula is -CH 2 CH 2 -, also known as ethylene group;

[0071] C 3 Alkylene: There are two structures, namely 1,2-propylene-CH 2 CH 2 CH 2 - and 1,3-propylene-CH 2 CH(CH 3 )-;

[0072] C 4 Alkylene: including 1,2-butylene -CH 2 CH 2 CH 2 CH 2 -、1,3-butylene-CH 2 CH 2 CH(CH 3 )-、1,4-butylene-CH 2 CH(CH 3 )CH 2 -、2,3-butylene-CH(CH 3 )CH(CH 3 )-wait;

[0073] C 5 Alkylene: including 1,2-pentylene -CH 2 CH 2 CH 2 CH 2 CH 2 -、1,3-pentylene-CH 2 CH 2 CH 2 CH(CH 3 )-、1,4-pentylene-CH 2 CH 2 CH(CH 3 )CH 2 -、1,5-pentylene-CH 2 CH(CH 3 )CH 2 CH 2 -、2,3-pentylene-CH 2 CH(CH 3 )CH(CH 3 )-、2,4-pentylene-CH(CH 3 )CH 2 CH(CH3 )-wait;

[0074] C 6 Alkylene: including 1,2-hexylene -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 -、1,3-hexamethylene-CH 2 CH 2 CH 2 CH 2 CH(CH 3 )-、1,4-hexamethylene-CH 2 CH 2 CH 2 CH(CH 3 )CH 2 -、1,5-hexamethylene-CH 2 CH 2 CH(CH 3 )CH 2 CH 2 -、1,6-Hexylene-CH 2 CH(CH 3 )CH 2 CH 2 CH 2 -、2,3-hexamethylene-CH 2 CH(CH 3 )CH 2 CH(CH 3 )-、2,4-hexamethylene-CH 2 CH(CH 3 )CH(CH 3 )CH 2 -、2,5-hexamethylene-CH(CH 3 )CH 2 CH(CH 3 )CH 2 -、3,4-hexamethylene-CH 2 CH(CH 2 CH 3 )CH(CH 3 )-wait;

[0075] C 7 Alkylene: including 1,2-heptylene -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 -、1,3-heptylene-CH2 CH 2 CH 2 CH 2 CH 2 CH(CH 3 )-、1,4-heptylene-CH 2 CH 2 CH 2 CH 2 CH(CH 3 )CH 2 - and so on, and so on, you can write a variety of structures;

[0076] C 8 Alkylene: including 1,2-octylene-CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 -、1,3-octylene-CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH(CH 3 )-、1,4-octylene-CH 2 CH 2 CH 2 CH 2 CH 2 CH(CH 3 )CH 2 -wait.

[0077] C 2 ~C 8 Alkoxyacyl refers to an acyl group (-CO-) and a C 1 ~C 7 Alkoxy (-OR, R is C 1 ~C 7 alkyl) group, the general formula is RO-CO-. For example, when R is methyl, the resulting methoxycarbonyl (CH 3 -O-CO-), which is C 2 Alkoxyacyl.

[0078] C 1 ~C 8 The alkyl group refers to a saturated hydrocarbon group containing 1 to 8 carbon atoms, including but not limited to one of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl and octyl.

[0079] In some of these examples, organic compounds substituted with C 1 ~C 8 Substituents in the alkyl group include hydroxyl, substituted or unsubstituted indolyl, substituted or unsubstituted C 6 ~C 20 Aromatic and substituted or unsubstituted C 3 ~C 8 At least one of cycloalkyl.

[0080] It can be understood that the indolyl group is the part that remains after removing a hydrogen atom from the indole molecule;

[0081] Aromatic group is the general term for the monovalent group remaining after removing a hydrogen atom from the aromatic carbon of the aromatic hydrocarbon molecule;

[0082] Cycloalkyl refers to an alkyl group with a cyclic carbon skeleton. Its carbon atoms are connected by single bonds to form a ring, and except for the chemical bonds forming the ring, the remaining bonds on each carbon atom are saturated with hydrogen atoms; including but not limited to cyclopropyl, cyclobutyl, cyclopentyl, etc.

[0083] It can be further understood that the substituted C 1 ~C 8 Alkyl groups include hydroxy substituted C 1 ~C 8 Alkyl, indolyl substituted C 1 ~C 8 Alkyl, C 6 ~C 20 Aromatically substituted C 1 ~C 8 Alkyl, C 3 ~C 8 Cycloalkyl substituted C 1 ~C 8 At least one of the alkyl groups; further, the indolyl-substituted C 1 ~C 8 The indolyl group in the alkyl group may be further substituted; C 6 ~C 20 Aromatically substituted C 1 ~C 8 The aromatic group in the alkyl group can be further substituted; C 3 ~C 8 Cycloalkyl substituted C 1 ~C 8 The cycloalkyl group in the alkyl group may be further substituted.

[0084] In some of these examples, organic compounds substituted with C 1 ~C 8 Substituents in the alkyl group include hydroxyl, substituted or unsubstituted indolyl, substituted or unsubstituted C 6 ~C12 Aromatic and substituted or unsubstituted C 5 ~C 7 At least one of cycloalkyl.

[0085] In some of these examples, in organic compounds, substituted or unsubstituted indolyl, substituted or unsubstituted C 6 ~C 20 Aromatic and substituted or unsubstituted C 3 ~C 8 Substituents in cycloalkyl groups include C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, hydroxyl, C 7 ~C 16 At least one of an aralkyloxy group, a halogen group and a nitro group.

[0086] Understandable, C. 2 ~C 6 Alkenyl refers to an unsaturated hydrocarbon group containing a carbon-carbon double bond (C=C) and having 2 to 6 carbon atoms. n H 2n - 1 (n=2~6), they are the groups left after removing a hydrogen atom from an olefin molecule;

[0087] C 7 ~C 16 Aralkyloxy is formed by chemical bonds between an aryl group (a group containing aromatic structures such as a benzene ring) and an alkoxy group (an alkyl group connected to an oxygen atom, with the general formula -OR, where R is an alkyl group), and the number of carbon atoms in the entire group is between 7 and 16.

[0088] Halogens include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

[0089] Further, the substituents in the substituted or unsubstituted indolyl group include C 1 ~C 6 Alkyl and C 2 ~C 6 Further, the substituents in the substituted or unsubstituted indolyl group include C 1 ~C 3 Alkyl and C 4 ~C 6 At least one of alkenyl groups.

[0090] Furthermore, substituted or unsubstituted C 6 ~C 20 Substituents in aromatic groups include hydroxyl, C 7 ~C 16At least one of aralkyloxy, halogen and nitro. Further, the substituted or unsubstituted C 6 ~C 20 Substituents in aromatic groups include hydroxyl, C 7 ~C 10 At least one of an aralkyloxy group, a halogen group and a nitro group.

[0091] In some of these examples, in organic compounds, R 1 is hydrogen, substituted or unsubstituted C 1 ~C 4 Alkyl and C 2 ~C 4 At least one of alkoxyacyl; or, R 1 and R 2 and the C atoms they are connected to form C 3 ~C 5 Cycloalkyl.

[0092] Furthermore, in some of these examples, in organic compounds, R 1 is hydrogen, substituted or unsubstituted C 1 ~C 2 Alkyl and C 2 ~C 3 At least one of alkoxyacyl; or, R 1 and R 2 and the C atoms they are connected to form C 4 ~C 5 Cycloalkyl.

[0093] In some of these examples, in organic compounds, R 1 is hydrogen, R 2 Selected from hydrogen, C 2 Alkoxyacyl or one of the structures of formula (II-1) to (II-10):

[0094]

[0095] Or, R 1 and R 2 Together with the C atom to which they are connected, they form a cyclobutyl group.

[0096] In some of the examples, in the organic compound, L is selected from one of a single bond and an ethylene group.

[0097] In some of the examples, the organic compound is selected from one of the structures of formula (III-1) to (III-12):

[0098]

[0099] An embodiment of the present application provides a method for preparing an organic compound, comprising the following steps:

[0100] (R)-3-phenyl-2-hydroxypropionic acid and the compound represented by formula (IV) are mixed for condensation reaction to generate a compound represented by formula (I):

[0101]

[0102] Among them, in formula (I) and formula (IV),

[0103] L is selected from a single bond and C 1 ~C 8 At least one of alkylene groups;

[0104] R 1 and R 2 are independently selected from hydrogen, substituted or unsubstituted C 1 ~C 8 Alkyl and C 2 ~C 8 At least one of alkoxyacyl; or, R 1 and R 2 and the C atoms they are connected to form C 3 ~C 8 Cycloalkyl.

[0105] In the preparation method of the organic compound, the carboxyl group of (R)-3-phenyl-2-hydroxypropionic acid and the amino group of the compound represented by formula (IV) are condensed to generate a compound represented by formula (I); the compound contains an amide bond, and the amide bond is connected to the R-configured carbon atom, has a bactericidal effect, and can effectively inhibit the activity of Escherichia coli and Staphylococcus aureus, and has good bactericidal stability and does not produce toxic substances.

[0106] The raw materials of the organic compound of the present application are cheap and readily available, and the preparation process is simple.

[0107] It can be understood that the above-mentioned organic compounds can be prepared by the preparation method of organic compounds provided in the present application, the preparation method of organic compounds provided in the present application can prepare the above-mentioned organic compounds, and the preparation method of organic compounds provided in the present application and the characteristics of the above-mentioned organic compounds can be mutually applicable.

[0108] It can be understood that (R)-3-phenyl-2-hydroxypropanoic acid, whose English name is (R)-2-Hydroxy-3-phenylpropanoic acid, has a structure as shown in formula (V):

[0109] .

[0110] In some of the examples, in the method for preparing an organic compound, the molar ratio of (R)-3-phenyl-2-hydroxypropionic acid to the compound represented by formula (IV) is 1-1.2:1.

[0111] In some of the examples, in the method for preparing an organic compound, the compound represented by formula (IV) includes at least one of the structures of formula (IV-1) to (IV-10):

[0112] .

[0113] In some of the examples, in the method for preparing an organic compound, a condensation reaction is carried out under the action of a catalyst, and the catalyst includes at least one of HOBT (1-hydroxybenzotriazole), EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) and DIPEA (N,N-diisopropylethylamine).

[0114] In some of the examples, in the method for preparing an organic compound, the catalyst includes HOBT, EDCI and DIPEA.

[0115] HOBT, EDCI and DIPEA promote acid-amine condensation. The specific principle is that under the catalytic action of DIPEA, EDCI reacts with the acid "(R)-3-phenyl-2-hydroxypropionic acid" to form an intermediate, and then quickly generates an active ester under the action of HOBT. The amine "compound of formula (IV)" as a nucleophilic agent attacks the active ester to obtain the target amine. The presence of HOBT makes the reaction easier, and the by-product urea generated is water-soluble and easy to remove.

[0116] Further, the molar ratio of HOBT, EDCI, DIPEA and (R)-3-phenyl-2-hydroxypropionic acid is 1-1.2: 1-1.2: 1-1.2: 1. Optionally, the molar ratio of HOBT, EDCI, DIPEA and (R)-3-phenyl-2-hydroxypropionic acid is 1:1:1:1.

[0117] In some of the examples, in the method for preparing an organic compound, the solvent for the condensation reaction includes DCM (dichloromethane).

[0118] In some of the examples, in the method for preparing an organic compound, the temperature of the condensation reaction is 15°C to 40°C.

[0119] In some of the examples, in the method for preparing an organic compound, after the condensation reaction is completed, the method further includes the step of post-treating the reaction solution obtained from the condensation reaction:

[0120] removing the solvent from the reaction solution to obtain a solid phase;

[0121] The solid phase is extracted with an organic solvent and water, and the organic phase is subjected to chromatography.

[0122] Further, the organic solvent includes DCM.

[0123] Further, the chromatographic treatment comprises column chromatography.

[0124] It is understood that the compounds represented by formula (IV-1) to (IV-10) can be purchased from the market or prepared by oneself.

[0125] In some of the examples, in the method for preparing an organic compound, the preparation of the compound represented by formula (IV-1) comprises the following steps:

[0126] (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionic acid hydrochloride, 1-bromo-3-methylbutene and an organic solvent are mixed to carry out a substitution reaction to prepare an N-dimethylpropenyl substituted indole intermediate compound;

[0127] Under acidic conditions, the N-dimethylpropylene substituted indole intermediate compound is subjected to a Boc group removal treatment to prepare a compound represented by formula (IV-1).

[0128] In some of the examples, in the preparation steps of the compound represented by formula (IV-1), the preparation of (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionic acid hydrochloride includes the following steps:

[0129] Using Boc 2 O The 2-amino group in (R)-2-amino-3-(1H-indol-3-yl)propionic acid hydrochloride is protected to prepare (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionic acid hydrochloride.

[0130] Furthermore, the amino group is protected in NaOH or NaHCO 3 The reaction was carried out under controlled alkaline conditions and in a mixed solvent of dioxane and water.

[0131] In some of the examples, in the method for preparing an organic compound, the preparation of the compound represented by formula (IV-2) comprises the following steps:

[0132] (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoic acid, CH 3 I. mixing a base and an organic solvent to carry out a substitution reaction to prepare an N-methyl substituted indole intermediate compound;

[0133] Under acidic conditions, the N-methyl substituted indole intermediate compound is subjected to a Boc group removal treatment to prepare a compound represented by formula (IV-2).

[0134] In some of the examples, in the preparation step of the compound represented by formula (IV-2), (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionic acid is first dissolved in an organic solvent, and then CH 3 I and a base. Further, (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionic acid and an organic solvent are mixed and stirred at -5°C to dissolve the (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionic acid in the organic solvent.

[0135] Furthermore, in the preparation step of the compound represented by formula (IV-2), the base includes but is not limited to KOH; further, the organic solvent includes but is not limited to DMSO. Further, the temperature of the substitution reaction is 15°C to 40°C.

[0136] In some of these examples, in the preparation step of the compound represented by formula (IV-2), the acid used in the Boc group removal treatment includes but is not limited to at least one of trifluoroacetic acid (TFA), hydrochloric acid (HCl), formic acid and p-toluenesulfonic acid.

[0137] Similarly, the reaction solution obtained from the above substitution reaction may also be post-treated using the above post-treatment steps for the condensation reaction.

[0138] The method for preparing an organic compound provided in the present application has a high yield of the obtained organic compound and less by-products.

[0139] One embodiment of the present application provides the use of the above organic compound or the organic compound prepared by the above preparation method in the preparation of a fungicide. Another embodiment of the present application provides a fungicide, comprising the above organic compound or the organic compound prepared by the above preparation method.

[0140] The bactericide prepared by using the above organic compound or the organic compound prepared by the above preparation method has good bactericidal ability, especially can effectively inhibit the activity of Escherichia coli and Staphylococcus aureus, and has good bactericidal stability, does not produce toxic substances, can also be widely used in households, and can be used for scaled-up production in the purification field.

[0141] An embodiment of the present application provides a purification device, comprising the above-mentioned bactericide.

[0142] It can be understood that the purification device includes but is not limited to a purifier, an air conditioner, etc.

[0143] The present application is further described in detail below in conjunction with specific implementation methods, but the implementation methods of the present application are not limited thereto.

[0144] The structures of the compounds represented by formula (III-1) to (III-12) prepared in each embodiment are as follows:

[0145]

[0146] Example 1

[0147] (1) (R)-2-amino-3-(1H-indol-3-yl)propionic acid hydrochloride (1 eq.), NaOH (1.2 eq.), and a mixed solvent (10 mL) of dioxane and water in a volume ratio of (5:1) were used to react the 2-amino group at room temperature for 24 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water three times, and the organic phase was dried and then separated by column chromatography to obtain (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionic acid hydrochloride;

[0148] (2) The (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionic acid hydrochloride prepared in step (1) was dissolved in DMSO (20 mL) and stirred at 0°C for 5 minutes, then 1-bromo-3-methylbutene (10.0 eq.) and KOH (3.0 eq.) were added, and the reaction was allowed to react at room temperature for 2 hours, and the reaction was monitored by TLC. After the reaction was complete, NH 4 The reaction was quenched with Cl, dried under reduced pressure, extracted three times with DCM and water, and the organic phase was dried and separated by column chromatography to obtain the N-dimethylacryl substituted indole intermediate compound;

[0149] (3) The N-dimethylpropylene substituted indole intermediate compound prepared in step (2) was dissolved in DCM, TFA (3.0 eq.) was added to remove Boc, and the reaction was monitored by TLC. After the reaction was completed, the mixture was dried under reduced pressure, extracted with DCM and water three times, the organic phase was dried, and then column chromatography was performed to obtain the compound represented by formula (IV-1);

[0150] (4) Add (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) to a DCM solution (50 mL) containing HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then dropwise add the DCM solution of the compound represented by formula (IV-1) obtained in step (3), and react at room temperature for 8 hours. TLC is used to track the reaction. After the reaction is complete, the mixture is dried under reduced pressure, extracted with DCM and water three times, the organic phase is dried, and then separated by column chromatography to obtain the product, which is detected to be the compound represented by formula (III-1). The hydrogen spectrum is as shown in FIG. Figure 1 shown.

[0151] Example 2

[0152] (1) (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionic acid was dissolved in DMSO and stirred at 0°C for 5 minutes, then MeI (10.0 eq.) and KOH (3.0 eq.) were added, reacted at room temperature for 2 hours, and the reaction was monitored by TLC. After the reaction was complete, NH 4 The reaction was quenched with Cl, dried under reduced pressure, extracted three times with DCM and water, and the organic phase was dried and separated by column chromatography to obtain the N-dimethylacryl substituted indole intermediate compound;

[0153] (2) The N-methyl substituted indole intermediate compound prepared in step (1) was dissolved in DCM, TFA (3.0 eq.) was added to remove Boc, and the reaction was monitored by TLC. After the reaction was completed, the mixture was dried under reduced pressure, extracted with DCM and water three times, the organic phase was dried, and then column chromatography was performed to obtain the compound represented by formula (IV-2);

[0154] (3) Add (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) to a DCM solution (50 mL) containing HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then dropwise add the DCM solution of the compound represented by formula (IV-2) obtained in step (2), and react at room temperature for 8 hours. TLC is used to track the reaction. After the reaction is complete, the mixture is dried under reduced pressure, extracted with DCM and water three times, the organic phase is dried, and then separated by column chromatography to obtain the product, which is detected to be the compound represented by formula (III-2). The hydrogen spectrum is shown in FIG. Figure 2 shown.

[0155] Example 3

[0156] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then a DCM solution of L-tyrosine hydrochloride was added dropwise to the above solution, and the reaction was carried out at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, the organic phase was dried, and then the product was separated by column chromatography, which was detected to be the compound shown in formula (III-3), and the hydrogen spectrum was as shown in FIG. Figure 3 shown.

[0157] Example 4

[0158] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then a DCM solution of (S)-2-amino-3-phenylpropionic acid hydrochloride was added dropwise to the above solution, and the reaction was carried out at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, the organic phase was dried, and then the product was separated by column chromatography, which was detected to be the compound shown in formula (III-4), and the hydrogen spectrum was as shown in FIG. Figure 4 shown.

[0159] Example 5

[0160] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then a DCM solution of (S)-2-amino-3-(4-(benzyloxy)phenyl)propionic acid hydrochloride was added dropwise to the above solution, and the reaction was carried out at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, the organic phase was dried, and then the product was separated by column chromatography, which was detected to be the compound shown in formula (III-5), and the hydrogen spectrum was as shown in FIG. Figure 5 shown.

[0161] Example 6

[0162] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then a DCM solution of (R)-2-amino-3-(4-chlorophenyl)propionic acid hydrochloride was added dropwise to the above solution, and the reaction was allowed to react at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, the organic phase was dried, and then the product was separated by column chromatography, which was detected to be the compound shown in formula (III-6), and the hydrogen spectrum was as shown in FIG. Figure 6 shown.

[0163] Example 7

[0164] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then a DCM solution of 4-nitro-L-phenylalanine hydrochloride was added dropwise to the above solution, and the reaction was carried out at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, the organic phase was dried, and then the product was separated by column chromatography, which was detected to be the compound shown in formula (III-7), and the hydrogen spectrum was as shown in FIG. Figure 7 shown.

[0165] Example 8

[0166] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then a DCM solution of (S)-2-aminopropionic acid hydrochloride was added dropwise to the above solution, and the reaction was allowed to react at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, the organic phase was dried, and then separated by column chromatography to obtain the product, which was detected to be the compound shown in formula (III-8), and the hydrogen spectrum was as shown below: Figure 8 shown.

[0167] Example 9

[0168] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then a DCM solution of DL-threonine hydrochloride was added dropwise to the above solution, and the reaction was carried out at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, the organic phase was dried, and then the product was separated by column chromatography, which was detected to be the compound shown in formula (III-9), and the hydrogen spectrum was as shown in FIG. Fig. 9 shown.

[0169] Example 10

[0170] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then the DCM solution of 1-aminocyclobutanecarboxylic acid was added dropwise to the above solution, and the reaction was carried out at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, the organic phase was dried, and then the product was separated by column chromatography, which was detected to be the compound shown in formula (III-10), and the hydrogen spectrum was as shown in FIG. Fig.10 shown.

[0171] Embodiment 11

[0172] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then a DCM solution of L-glutamic acid dicarboxylic acid hydrochloride was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, and the organic phase was dried. The product was then separated by column chromatography, and was detected to be the compound of formula (III-11). The hydrogen spectrum was as shown in FIG. Fig.11 shown.

[0173] Example 12

[0174] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a DCM (50 mL) solution of HOBt (1.0 eq.), EDCI (1.0 eq.) and DIPEA (1.0 eq.), and then a DCM solution of (S)-2-amino-3-cyclohexylpropionic acid hydrochloride was added dropwise to the above solution, and the reaction was allowed to react at room temperature for 8 hours, and the reaction was followed by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted with DCM and water for 3 times, the organic phase was dried, and then separated by column chromatography to obtain the product, which was detected to be the compound shown in formula (III-12), and the hydrogen spectrum was as shown in FIG. Fig.12 shown.

[0175] The organic compounds prepared in each embodiment were subjected to a bactericidal test, and the test method was as follows: 1 mg of the final product was dissolved in 0.6 mL of chromatographic methanol to verify that the purity of the compounds represented by formula (III-1) to (III-12) reached 99.99%, and then 1 mg of the final product was dissolved in 1 mL of DMSO to obtain an organic compound solution; after spraying the organic compound solution on the culture dish, the survival rates of Escherichia coli and Staphylococcus aureus were observed at different times (5 min, 6 h, 24 h). The results are shown in Table 1.

[0176] Table 1

[0177]

[0178] It can be seen from Table 1 that the compounds prepared in various examples have good bactericidal effects.

[0179] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0180] The above-described embodiments only express several implementation methods of the present application, which is convenient for understanding the technical solution of the present application in detail, but it cannot be understood as limiting the scope of protection of the invention patent. It should be pointed out that for ordinary technicians in this field, without departing from the concept of the present application, several modifications and improvements can be made, which all belong to the scope of protection of the present application. It should be understood that the technical solutions obtained by those skilled in the art through logical analysis, reasoning or limited experiments on the basis of the technical solutions provided in the present application are all within the scope of protection of the claims attached to the present application. Therefore, the scope of protection of the patent of this application shall be based on the content of the attached claims, and the description can be used to interpret the content of the claims.

Claims

1. An organic compound, characterized in that It has the general formula shown in formula (I): Wherein, L is selected from at least one of a single bond and a C1~C8 alkylene group; R1 and R2 are independently selected from at least one of hydrogen, substituted or unsubstituted C1~C8 alkyl and C2~C8 alkoxyacyl; or, R1 and R2 and the C atom to which they are connected together form a C3~C8 cycloalkyl group.

2. The organic compound according to claim 1, characterized in that The substituents in the substituted C1~C8 alkyl group include hydroxyl, substituted or unsubstituted indolyl, substituted or unsubstituted C6~C 20 At least one of an aromatic group and a substituted or unsubstituted C3~C8 cycloalkyl group.

3. The organic compound according to claim 2, characterized in that The substituted or unsubstituted indolyl, the substituted or unsubstituted C6~C 20 The substituents in the aromatic group and the substituted or unsubstituted C3~C8 cycloalkyl group include C1~C6 alkyl, C2~C6 alkenyl, hydroxyl, C7~C 16 At least one of an aralkyloxy group, a halogen group and a nitro group.

4. The organic compound according to claim 3, characterized in that The substituent in the substituted or unsubstituted indolyl group includes at least one of a C1-C6 alkyl group and a C2-C6 alkenyl group; and / or The substituted or unsubstituted C6~C 20 Substituents in aromatic groups include hydroxyl, C7~C 16 At least one of an aralkyloxy group, a halogen group and a nitro group.

5. The organic compound according to claim 4, characterized in that R1 is hydrogen, and R2 is selected from hydrogen, C2 alkoxy acyl or one of the structures of formula (II-1) to (II-10): Alternatively, R1 and R2 and the C atom to which they are commonly attached form a cyclobutyl group.

6. The organic compound according to any one of claims 1 to 5, characterized in that L is selected from one of a single bond and an ethylene group.

7. The organic compound according to claim 1, characterized in that The organic compound is selected from one of the structures of formula (III-1) to (III-12): 。 8. A method for preparing an organic compound, characterized in that: The following steps are involved: (R)-3-phenyl-2-hydroxypropionic acid and the compound represented by formula (IV) are mixed for condensation reaction to generate the compound represented by formula (I): Among them, in formula (I) and formula (IV), L is selected from at least one of a single bond and a C1-C8 alkylene group; R1 and R2 are independently selected from at least one of hydrogen, substituted or unsubstituted C1~C8 alkyl and C2~C8 alkoxyacyl; or, R1 and R2 and the C atom to which they are connected together form a C3~C8 cycloalkyl group.

9. The method for preparing an organic compound according to claim 8, characterized in that: The compound represented by formula (IV) includes at least one of the structures of formula (IV-1) to (IV-10): 。 10. The method for preparing an organic compound according to any one of claims 8 to 9, characterized in that: The condensation reaction is carried out under the action of a catalyst, wherein the catalyst comprises at least one of HOBT, EDCI and DIPEA; and / or The solvent for the condensation reaction included DCM.

11. Use of the organic compound according to any one of claims 1 to 7 or the organic compound prepared by the preparation method according to any one of claims 8 to 10 in the preparation of a fungicide.

12. A bactericide, characterized in that: The method comprises the organic compound as claimed in any one of claims 1 to 7 or the organic compound prepared by the preparation method as claimed in any one of claims 8 to 10.

13. A purification device, characterized in that: Comprising the bactericide as claimed in claim 12.

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