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Method for converting trans-vinylcyclopropane to cis-vinylcyclopropane

A vinylcyclopropane and basecyclopropane technology, which is applied in the field of conversion of trans-vinylcyclopropane to cis-vinylcyclopropane, can solve the problem that chiral catalysts or optically pure raw materials are expensive, limited in application, and rare in starting materials. And other issues

Inactive Publication Date: 2011-01-19
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, they have disadvantages such as rare starting materials, harsh reaction conditions, expensive chiral catalysts or optically pure raw materials, which greatly limit the application of these compounds in the fields of organic chemistry and medicinal chemistry.

Method used

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  • Method for converting trans-vinylcyclopropane to cis-vinylcyclopropane
  • Method for converting trans-vinylcyclopropane to cis-vinylcyclopropane
  • Method for converting trans-vinylcyclopropane to cis-vinylcyclopropane

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Experimental program
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Effect test

Embodiment 1

[0023] 1 H NMR determination of the trans-vinylcyclopropane / cis-vinyl ring in the synthesized 2-vinyl-1-acetyl-N-(4-chlorophenyl)-1-amidocyclopropane stereoisomer mixture Propane=5; Add acetonitrile (5.0 ml) and this vinylcyclopropane stereoisomer mixture (0.527 g, 2.0 mmol) and lithium chloride (0.254 g, 6.0 mmol) in a 25 ml round bottom flask; room temperature Stir for 10 hours; the reaction solution is poured into 30 milliliters of water, suction filtered, and air-dried to obtain 0.519 grams of solid, which is subjected to 1 H NMR detection, cis-vinylcyclopropane / trans-vinylcyclopropane=8.5; separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=5 / 1) to obtain white solid cis-2-ethylene Base-1-acetyl-N-(4-chlorophenyl)-1-amidocyclopropane 0.464 gram, trans-vinylcyclopropane is transformed into cis-vinylcyclopropane and the transformation efficiency is 87%; Conversion is as follows :

[0024]

Embodiment 2

[0026] 1 H NMR technique identified trans-vinylcyclopropane / cis-vinyl in the synthesized 2-vinyl-1-acetyl-N-(2-methylphenyl)-1-amidocyclopropane stereoisomer mixture Cyclopropane=6; Acetonitrile (5.0 mL) and this vinylcyclopropane stereoisomer mixture (0.487 g, 2.0 mmol) and lithium chloride (0.254 g, 6.0 mmol) were added to a 25 mL round bottom flask; Stir at room temperature for 10 hours; the reaction solution was poured into 30 ml of water, suction filtered, and air-dried to obtain 0.479 g of solid, which was subjected to 1H NMR detection, cis-vinylcyclopropane / trans-vinylcyclopropane=8.7; separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=5 / 1) to obtain white solid cis-2-ethylene 0.430 g of yl-1-acetyl-N-(2-methylphenyl)-1-amidocyclopropane, the conversion rate of trans-vinylcyclopropane to cis-vinylcyclopropane was 87%; the conversion was as follows Mode:

[0027]

Embodiment 3

[0029] 1 H NMR technique determination of trans-vinylcyclopropane / cis-ethylene in the synthesized mixture of 2-vinyl-1-acetyl-N-(4-methoxyphenyl)-1-amidocyclopropane stereoisomers Cyclopropane=6.5; Add acetonitrile (5.0 milliliters) and this vinyl cyclopropane stereoisomer mixture (0.519 gram, 2.0 mmol) and lithium chloride (0.254 gram, 6.0 mmol) in 25 milliliters of round bottom flasks Stir at room temperature for 10 hours; The reaction solution was poured into 30 milliliters of water, suction filtered, and air-dried to obtain 0.511 grams of solids, which were subjected to 1 H NMR detection, cis-vinylcyclopropane / trans-vinylcyclopropane=8.2; separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=5 / 1) to obtain white solid cis-2-ethylene Base-1-acetyl-N-(4-methoxyphenyl)-1-amidocyclopropane 0.455 grams, trans-vinylcyclopropane to cis-vinylcyclopropane conversion conversion rate of 86%; conversion as follows:

[0030]

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Abstract

The invention belongs to the technical field of the organic synthetic chemistry and relates to a method for converting trans-vinylcyclopropane to cis-vinylcyclopropane. The method comprises the following steps: firstly synthesizing vinylcyclopropane stereoisomers according to the literature, adding the vinylcyclopropane stereoisomers and metal halide in organic solvent, stirring at the room temperature, and performing silica gel column chromatography for separation and other processes to realize the aim. For different substituents, the conversion rate ranges from 86% to 87%. The metal chloride used in the method is cheap and accessible, the reaction conditions are wild, the conversion rate is high, the operation is simple, and the technology and industrial production are easy to realize.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry and relates to a method for converting trans-vinyl cyclopropane to cis-vinyl cyclopropane. Background technique [0002] Stereoisomerism is ubiquitous in organic chemistry and has a great influence on the physical and chemical properties of compounds. For example, Thalidomide (commonly known as "thalidomide") has two stereoisomers. The dextrorotary form can act as a sedative and effectively inhibit the pregnancy reaction of pregnant women, while the levorotatory form can cause fetal malformation. Therefore, it is the ideal of many synthetic chemists and medicinal chemists to obtain compounds with single stereo configuration. Vinylcyclopropane structural units with a single stereo configuration widely exist in natural products, many of which have been proven to have good medicinal value, such as pyrethroids (Pyrethroids in Agrochemicals from Nature Products, 1995, 147-213.), an...

Claims

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Application Information

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IPC IPC(8): C07B35/08C07C235/82C07C231/16
Inventor 李燕张前倪志坤刘群
Owner NORTHEAST NORMAL UNIVERSITY
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