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Synthesis method of polycyclic disubstituted 1,3-propanedione compound

A synthesis method and compound technology, applied in the field of organic compound synthesis, can solve the problems of high operating level requirements, unsuitable for industrial production, easy to generate hydrogen, etc., and achieve the effects of easy operation, not easy to flash explosion, and promoting the reaction to occur.

Active Publication Date: 2020-06-12
苏州爱玛特生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]However, sodium hydride is used to participate in the reaction in the synthesis method, and hydrogen gas is easily generated during the reaction process, which is prone to flash explosion and is unsafe. Industrial production

Method used

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  • Synthesis method of polycyclic disubstituted 1,3-propanedione compound
  • Synthesis method of polycyclic disubstituted 1,3-propanedione compound
  • Synthesis method of polycyclic disubstituted 1,3-propanedione compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 1,3-dicyclohexyl-1,3-propanedione

[0031]

[0032] Under the condition of nitrogen protection, 1-cyclohexyl-1-ethanone (18.9g, 150mmol,) and methyl cyclohexanecarboxylate (14.2g, 100mmol) were dissolved in 80mL of anhydrous tetrahydrofuran, and potassium amide (11.0g , 200mmol), stirred at room temperature (23°C) for 3.5h. After the reaction, the reaction solution was poured into ice water, and diethyl ether was added to separate the layers. The aqueous layer was first adjusted to pH=5.0 with 2N HCl, and then Na 2 CO 3 Adjust to pH=7.5, extract with ether, and dry over anhydrous magnesium sulfate. Most of the solvent was spun off, purified by silica gel column chromatography, and eluted with dichloromethane / methanol (V / V=20 / 1) to obtain 1,3-dicyclohexyl-1,3-propanedione (19.9g ). Yield: 84%.

[0033] NMR test results:

[0034] 1 H NMR (400MHz, CDCl 3 )δ15.75(br,1H),5.49(s,1H),2.21-2.14(m,2H),1.88-1.79(m,8H),1.73-1.68(m,2H),1.41-1.17(m, 10H).

Embodiment 2

[0036] Synthesis of 1,3-dicyclopentyl-1,3-propanedione

[0037]

[0038] The raw materials used in this example are 1-cyclopentyl-1-ethanone and methyl cyclopentacarboxylate, the molar ratio of 1-cyclopentyl-1-ethanone and methyl cyclopentacarboxylate is 1.5:1, other As in Example 1, 1,3-dicyclopentyl-1,3-propanedione was finally obtained with a yield of 85%.

[0039] NMR test results:

[0040] 1 H NMR (400MHz, CDCl 3 )δ15.66(br,1H),5.56(m,1H),2.59(m,1H),2.44(m,1H),1.79-1.76(m,3H),1.74(m,1H),1.70-1.65 (m,10H).

[0041] 13 C NMR (125MHz, CDCl 3 )δ205.00(d), 54.62(dt), 51.13(dtd), 28.91(dt), 25.50(td).

Embodiment 3

[0043] Synthesis of 1,3-dicyclobutyl-1,3-propanedione

[0044]

[0045] The raw materials used in this example are 1-cyclobutyl-1-ethanone and methyl cyclobutanecarboxylate, the molar ratio of 1-cyclobutyl-1-ethanone and methyl cyclobutanecarboxylate is 1.5:1, other As in Example 1, 1,3-dicyclobutyl-1,3-propanedione was finally obtained with a yield of 85%.

[0046] NMR test results:

[0047] 1 H NMR (400MHz, CDCl 3 )δ5.56(d,1H),2.67(m,1H),2.47(m,1H),1.99-1.94(m,8H),1.76-1.73(m,4H).

[0048] 13 C NMR (125MHz, CDCl 3 )δ205.08(d), 55.10(dt), 47.45(dh), 28.07(t), 20.56(dt).

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Abstract

The invention relates to a synthesis method of a polycyclic disubstituted 1,3-propanedione compound. The structural formula of the 1,3-propanedione compound is represented by formula I. A compound represented by formula II reacts with a compound represented by formula III at 10-30 DEG C under the protection of an inert gas in the presence of potassium amide and tetrahydrofuran to prepare the compound represented by the formula I; and the structural formula of the compound shown of the formula I is shown in the specification, the structural formula of the compound shown of formula II is shown in the specification, the structural formula of the compound of formula III is shown in the specification, and in the formulas, R1 and R2 are independently selected from C3-C6 naphthenic bases. According to the synthesis method, potassium amide is adopted as a condensation accelerant, so reaction promotion is facilitated, reaction is safe and efficient, flash explosion is not prone to happening, and operation and synthesis are easy; and tetrahydrofuran is used as a solvent in a matched mode, so the reaction temperature is mild, reaction energy consumption can be reduced, reaction is easy, convenient and efficient, and the synthesis method is more suitable for industrial production. Compared with an existing synthesis method, the method is milder and easier to operate.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a method for synthesizing polycyclic ring disubstituted 1,3-propanedione compounds. Background technique [0002] Polycyclic disubstituted 1,3-propanedione compounds are an important class of pharmaceutical intermediates, such as synthetic intermediates used in the synthesis of herbicides, and are widely used in the field of medicinal chemistry. [0003] The synthesis method of 1,3-propanedione is mostly made by the condensation reaction of ketone and ester, while for the condensation reaction of polycyclic substituted ketone and polycyclic substituted ester, the commonly used method is polycyclic substitution Condensation reactions of ketones with polycyclic ring-substituted esters in the presence of sodium hydride and organic solvents, as described in References: Sawa M, Dr. Kazuhiro Morisaki, Kondo Y, et al. Direct Access to N-Unprotectedα-and / or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/45C07C49/313
CPCC07C45/455C07C2601/02C07C2601/04C07C2601/08C07C2601/14C07C49/313
Inventor 汪明中朱明新苏道李金金
Owner 苏州爱玛特生物科技有限公司
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