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Method for synthesizing caulerpin

A technology for synthesizing phycoerythrin and phycoerythrin, which is applied in organic chemistry and other fields, can solve the problems of low yield and achieve the effects of easy-to-obtain raw materials, mild reaction conditions, and easy synthesis

Inactive Publication Date: 2014-09-03
SHANGHAI MARITIME UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method starts from 2-(2'-indole)-methyl acetate, undergoes Vilsmeier formylation (Vilsmeier formylation) reaction, and the obtained intermediate is dimerized and condensed to generate fern phycoerythrin---the key point of this method very low yield

Method used

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  • Method for synthesizing caulerpin
  • Method for synthesizing caulerpin

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Step 1: Dimethyl 3-oxo-1,5-pentanedioate (17.4 g) was added dropwise to phenylhydrazine (10.8 g) under magnetic stirring at room temperature. Two drops of acetic acid were then added and stirring was continued for 3 hours. Concentrated sulfuric acid (20 ml) was added dropwise to the above reactant, stirred for 30 minutes, poured into crushed ice (200 g), and a pale yellow solid was precipitated, which was identified as 2-(3'-methoxycarbonyl)indole - methyl acetate (compound 4). 1 H NMR ( CDCl 3 , 400MHz ): δ 10.97 (bs, 1H), 8.08-8.04 (m, 1H), 7.49-7.46 ( m, 1H), 7.22-7.16 ( m, 2H ), 4.32 ( s, 2H ), 3.92 ( s, 3H ), 3.67 ( s, 3H ). 13 C NMR (CDCl 3 , 100MHz ): δ 171.39, 166.11, 138.56, 134.78, 126.36, 122.91, 121.92, 121.51, 111.17, 105.21, 52.46, 50.91, 32.10.

[0033] Step 2: Dissolve 2-(3'-methoxycarbonyl)indole-acetic acid methyl ester (2.5 g) in methanol (25 ml), add sodium methoxide (0.6 g), stir at room temperature for 3 days, acidify with concentrated hydroch...

Embodiment 2

[0036] Step 1: Dimethyl 3-oxo-1,5-pentanedioate (17.4 g) was added dropwise to phenylhydrazine (8.8 g) under magnetic stirring at room temperature. Then two drops of formic acid were added and stirring was continued for 1 hour. Concentrated sulfuric acid (20 ml) was added dropwise to the above reactant, stirred at 50°C for 30 minutes, poured into crushed ice (200 g), and a pale yellow solid was precipitated, which was identified as 2-(3'-methoxycarbonyl ) indole-methyl acetate.

[0037] Step 2: Dissolve 2-(3'-methoxycarbonyl)indole-acetic acid methyl ester (2.5 g) in methanol (25 ml), add sodium methoxide (0.3 g), stir at 65°C for 3 days, and use Acidify with concentrated hydrochloric acid to pH=5. Concentrate on a rotary evaporator, remove 3 / 4 volume of solvent, add water (5 ml) dropwise to the residue, and precipitate a light gray precipitate, which is identified as an intermediate ５ .

[0038] Step 3: Intermediates ５ (2 g) was dissolved in methanol (20 ml), and palladi...

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Abstract

The invention discloses a method for synthesizing caulerpin. In the method, the caulerpin is prepared from phenylhydrazine and 3-oxo-1,5-dimethyl glutarate by the following synthesis route. The method comprises the following steps: 1. carrying out Fischer indole reaction on phenylhydrazine 2 and 3-oxo-1,5-dimethyl glutarate 3 by using an acid catalyst to obtain methyl 2-(3'-methoxycarbonyl)indolyl-acetate 4; 2. carrying out Claisen ester condensation on the methyl 2-(3'-methoxycarbonyl)indolyl-acetate 4 by using an alkali catalyst to prepare an intermediate 5; and 3. carrying out catalytic hydrogenation or NaBH4 reduction on the intermediate 5, and dehydrating to obtain the caulerpin 1.Compared with the existing caulerpin synthesis route, the synthesis method disclosed by the invention has the advantage of cheap and accessible raw materials; the reaction conditions are mild, and every step can be performed at normal temperature; and the method is simple and convenient to operate, is easy for mass synthesis, and is applicable to industrial production.

Description

technical field [0001] The invention relates to a chemical method for synthesizing phycoerythrin. Background technique [0002] Caulerpin is a secondary metabolite extracted from seaweed, which has a variety of significant biological activities. [0003] [0004] (1) The application prospect of phycoerythrin as plant growth hormone [0005] Studies have shown that phycoerythrin can effectively promote the growth and development of soybean adventitious roots, and the effective concentration is very low. In the future, phycoerythrin may be used as a substitute for auxin and be widely used in agricultural production. (Wu Lunxiu, He Tingyu, Gu Wenxiang, Wang Jinxiang, Phycoerythrin promotes the formation of adventitious roots from soybean cuttings, Plant Physiology Communications, 2010, 46 (9), 895-901.) [0006] Phycoerythrin has both the properties of a growth promoter and a growth inhibitor similar to ethylene, so it can promote or inhibit growth, delay fruit ripening a...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 王军华任洪敏张希琴
Owner SHANGHAI MARITIME UNIVERSITY
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