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Cyclopentane coumarin compound and preparation method thereof

A technology for coumarins and compounds is applied in the field of cyclopentane coumarin compounds and their preparation, and achieves the effects of fast reaction speed, easy separation and purification, and rich diversity

Pending Publication Date: 2021-07-02
SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, there are still few reports on the mild and efficient synthesis of cyclopentanecoumarins from simple raw materials

Method used

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  • Cyclopentane coumarin compound and preparation method thereof
  • Cyclopentane coumarin compound and preparation method thereof
  • Cyclopentane coumarin compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Put 28.5mg (0.1mmol) of compound 1a, 41.2mg (0.12mmol) of compound 2a and 1mL of tetrahydrofuran into a dry 15mL Shrek tube, add 3.0mg (0.02mmol) of 1,8-diazabicyclonedecyl Carb-7-ene mixed for cycloaddition reaction. In the reaction system, the molar ratio of Compound 1a to Compound 2a is 1:1.2, 1,8-diazabicycloundec-7-ene accounts for 20% of the molar percentage of Compound 1a, and stirred at 25°C After 12 hours, it was concentrated with a rotary evaporator, and purified through a silica gel column (dichloromethane:petroleum ether=2:1, v / v) to obtain 54.0 mg of product 3aa with a yield of 85%.

[0050]

Embodiment 2

[0052]Put 28.5mg (0.1mmol) of compound 1a, 41.2mg (0.12mmol) of compound 2a and 1mL of tetrahydrofuran into a dry 15mL Shrek tube, add 2.2mg (0.02mmol) of triethylenediamine (DABCO) and mix well for ring Addition reaction. In the reaction system, the molar ratio of compound 1a to compound 2a is 1:1.2, triethylenediamine (DABCO) accounts for 20% of the molar percentage of compound 1a, stirred at 25°C for 12 hours, and concentrated with a rotary evaporator, Purified on a silica gel column (dichloromethane:petroleum ether=2:1, v / v) to obtain 35.8 mg of product 3aa with a yield of 57%.

[0053]

[0054] Compared with Example 1, the catalyst is replaced by DABCO, and others are the same as Example 1.

Embodiment 3

[0056] Put 28.5mg (0.1mmol) of compound 1a, 41.2mg (0.12mmol) of compound 2a and 1mL of tetrahydrofuran into a dry 15mL Shrek tube, add 2.4mg (0.02mmol) of 4-dimethylaminopyridine (DMAP) and mix well Carry out a cycloaddition reaction. In the reaction system, the molar ratio of compound 1a to compound 2a is 1:1.2, 4-dimethylaminopyridine (DMAP) accounts for 20% of the molar percentage of compound 1a, stirred at 25° C. for 12 hours, and Concentrate and purify through a silica gel column (dichloromethane:petroleum ether=2:1, v / v) to obtain 39.0 mg of product 3aa with a yield of 62%.

[0057]

[0058] Compared with Example 1, the catalyst is replaced by DMAP, and others are the same as Example 1.

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Abstract

The invention discloses a cyclopentane coumarin compound and a preparation method thereof, and belongs to the field of synthesis of organic compounds. The cyclopentane coumarin compound is synthesized in one step by taking cyclic azadiene and a 3-acetyl coumarin derivative as reaction raw materials. The cyclopentane coumarin compound is obtained by carrying out cycloaddition reaction on cyclic aza-diene and a 3-acetylcoumarin derivative by taking an organic base as a catalyst and stirring at room temperature under the condition of nitrogen protection. Preliminary verification shows that the compound synthesized by the invention has the characteristic of resisting phytopathogen activity. The reaction is an atom economical reaction, the reaction condition is mild, the reaction rate is high, the operation is simple and convenient, the side reaction is few, the product is convenient to purify, the yield is high, and the large-scale preparation can be realized. The invention provides a simple and feasible novel method for synthesizing the cyclopentane and coumarin compound.

Description

technical field [0001] The invention relates to the field of organic compound synthesis, in particular to a cyclopentanecoumarin compound and a preparation method thereof. Background technique [0002] Coumarins and cyclopentanes widely exist in natural products and exhibit a series of biological and pharmaceutical activities (Med.Res.Rev.2003,23,322; Nat.Prod.Rep.2015,32,1472; Drugs , 2002,62,107), and the cyclopentanecoumarin derivatives formed by combining two types of skeletons also show certain activity, for example, the well-known aflatoxin is a derivative of this type of compound (Pharmac.Ther .1995,65,163.), In addition, Herbertenolide belongs to the sesquiterpenes of the phyllonane type. The sesquiterpenes of this family exhibit significant growth inhibitory activity against phytopathogenic fungi, and are expected to be developed as antifungal pesticides (J. Chem. Soc. Perkin Trans. 1, 1986, 701). Although there are many reports (Tetrahedron, 2001, 57, 9299; Org. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D419/04C07D419/14C07D417/04A01N43/88A01N43/80A01P3/00
CPCC07D419/04C07D419/14C07D417/04A01N43/88A01N43/80
Inventor 袁春浩林华伟邹楠葛燕青
Owner SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
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