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Synthesis method of cyclopropane compounds

A synthetic method and compound technology, applied in the field of organic synthesis, can solve the problems of environmental pollution, low yield, long reaction time, etc., and achieve the effect of high reaction efficiency, good repeatability, and short time

Active Publication Date: 2020-10-02
ASYMCHEM LIFE SCI TIANJIN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The main purpose of the present invention is to provide a synthetic method of cyclopropane compounds, to solve the problems of environmental pollution, long reaction time or low yield when synthesizing cyclopropane compounds in the prior art

Method used

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  • Synthesis method of cyclopropane compounds
  • Synthesis method of cyclopropane compounds
  • Synthesis method of cyclopropane compounds

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preparation example Construction

[0031] The synthesis method comprises: reacting olefin compound A and ethyl diazoacetate under the catalysis of a supported rhodium catalyst to obtain cyclopropane compounds; wherein the structural formula of olefin compound A is , R 1 , R 2 , R 3 , R 4 has the same definition as above.

[0032] The present invention catalyzes olefin compound A with supported rhodium catalyst React with ethyl diazoacetate to synthesize propane compounds. By adopting the synthesis method provided by the invention, the reaction efficiency is high, the time is short, the yield can even reach more than 90%, and the repeatability is good. Moreover, in the synthesis method, there is no need to use additives like copper halide or acetyl halide, and what is used is a supported rhodium catalyst, which has high environmental protection.

[0033] For olefin compound A For the different substituents in the present invention, whether it is H, furyl, ester group, C 1 ~C 4 Alkyl substituted ester...

Embodiment 1

[0043]

[0044] The rhodium supported catalyst (15 g) was packed into a column reactor (150 mL). Dissolve styrene (10.415g, 0.1mol) and EDA (5.705g, 0.3mol) in dichloromethane (10v), stir and clarify, then pump them into the columnar reactor at a speed of 10g / min with a back pressure of 1.0 MPa, retention time 15min, reaction temperature 25°C, outlet sampling GC. The reaction system was washed with water (10v) and separated. The organic phase was concentrated to obtain 18.2 g of reddish-brown liquid, with an isolated yield of 91%. 1 H NMR (500 MHz, Chloroform-d)δ 7.33 – 7.26 (m, 2H), 7.26 – 7.16 (m, 3H), 4.12 (qd, J = 8.0, 1.4 Hz, 2H), 2.71 (q, J = 6.9 Hz, 1H), 2.44 (q, J = 7.1 Hz, 1H), 1.88 (dt, J = 12.5, 7.0Hz, 1H), 1.77 (dt, J = 12.5, 7.0 Hz, 1H), 1.23 (t, J = 8.0 Hz, 3H).

Embodiment 2

[0046] The rhodium supported catalyst (15 g) was packed into a column reactor (150 mL). Dissolve styrene (10.415g, 0.1mol) and EDA (5.705g, 0.3mol) in ethyl acetate (10v) and stir to clarify, then pump them into the columnar reactor at a speed of 10g / min with a back pressure of 1.0 MPa, retention time 15min, reaction temperature 25°C, outlet sampling GC. The reaction system was washed with water (10v) and separated. The organic phase was concentrated to obtain 17.3 g of reddish-brown liquid, with an isolated yield of 81%. 1 H NMR (500 MHz, Chloroform-d)δ 7.33 – 7.26 (m, 2H), 7.26 – 7.16 (m, 3H), 4.12 (qd, J = 8.0, 1.4 Hz, 2H), 2.71 (q, J = 6.9 Hz, 1H), 2.44 (q, J = 7.1 Hz, 1H), 1.88 (dt, J = 12.5, 7.0Hz, 1H), 1.77 (dt, J = 12.5, 7.0 Hz, 1H), 1.23 (t, J = 8.0 Hz, 3H).

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Abstract

The invention provides a synthesis method of cyclopropane compounds. The cyclopropane compounds have a structure as shown in a general formula I which is described in the specification. The synthesismethod comprises the following step: reacting olefin compounds A with ethyl diazoacetate under the catalytic action of a supported rhodium catalyst to obtain the cyclopropane compounds, wherein the structural formula of the olefin compounds A is shown in the specification. The synthesis method provided by the invention has the advantages of high reaction efficiency, short time, yield even reaching90% or above, and good repeatability. In addition, copper halide or an acetyl halide similar additive is not needed in the synthesis method, and the supported rhodium catalyst is adopted, so that theenvironmental protection property is relatively high.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing cyclopropane compounds. Background technique [0002] The cyclopropyl structure widely exists in natural products and drug molecules with biological activity. At present, people have isolated different metabolites containing cyclopropane structure from organisms such as plants, fungi, and microorganisms, which cover various types of molecules such as terpenoids, fatty acids, pheromones, and amino acids. The research on introducing the cyclopropyl structure into drug molecules has also gradually emerged since the 1960s. The FDA of the United States has approved many drugs containing cyclopropyl groups, and the introduction of cyclopropyl groups meets the specific drug effects of the drugs. Medicinal chemistry has incorporated cyclopropyl into pharmaceutically active small molecule pharmacodynamic fragments. [0003] The synthetic routes of cyclopropana...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C231/12C07C253/30C07F7/18C07B37/10C07C69/743C07C69/757C07C233/58C07C255/46C07C69/753C07D307/54
CPCC07C67/343C07C231/12C07C253/30C07F7/1892C07B37/10C07D307/54C07C2601/02C07C69/743C07C69/757C07C233/58C07C255/46C07C69/753
Inventor 洪浩张恩选刘志清卢江平宋迪敬大江
Owner ASYMCHEM LIFE SCI TIANJIN
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