Method for synthesizing beta-iodobutyl lactone

A technology of iodobutenoic acid lactone and allenoic acid ester is applied in the field of synthesizing β-iodobutenoic acid lactone, can solve the problems of low hydrolysis yield, isomerization and the like, and achieves low cost and high reaction efficiency. Short time, high yield effect

Inactive Publication Date: 2005-12-21
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because 2,3-alkenoic acid is hydrolyzed by 2,3-alkenoic acid ester under acid or base catalysis, under this condition,

Method used

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  • Method for synthesizing beta-iodobutyl lactone
  • Method for synthesizing beta-iodobutyl lactone
  • Method for synthesizing beta-iodobutyl lactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add ethyl 2,3-heptadienoate (81.9mg, 0.53mmol), MeCN (4mL), water (0.27mL) into a 25mL egg-shaped flask, add iodine (254mg, 1.0mmol) under stirring, and continue to The reaction was stirred for 12 hours. Water (6 mL) was added to the reaction solution to quench, and saturated sodium thiosulfate eliminated excess iodine. Extract with ether, dry over anhydrous sodium sulfate, filter, concentrate, and perform flash column chromatography to obtain 94.9 mg of the product 3-iodo-γ-heptenolactone with a yield of 71%. The product was a white solid with a melting point of 57-58°C.

[0021] 1 H NMR (400MHz, CDCl 3 )δ6.45(s, 1H), 4.89-4.92(m, 1H), 1.67-1.98(m, 1H), 1.50-1.55(m, 1H), 1.35-1.42(m, 2H), 0.91(t, J=6Hz, 3H);

[0022] 13 C NMR (100MHz, CDCl 3 )δ171.1, 129.9, 125.5, 87.9, 34.6, 17.3, 13.7;

[0023] MS (70eV, EI) m / z (%): 253 (M + +1, 100);

[0024] IR(KBr)v(cm -1 ) 1738, 1582, 1296, 1168.

Embodiment 2

[0026] Add 2,3-heptadienoic acid ethyl ester (81.4mg, 0.52mmol), MeCN (4mL), water (0.27mL) in 25mL egg-shaped bottle, add iodine (381.8mg, 1.5mmol) under stirring, continue to The reaction was stirred at room temperature for 12 hours. The rest were the same as in Example 1, and 94.7 mg of the product 3-iodo-γ-heptenolactone was obtained with a yield of 71%. The product was a white solid with a melting point of 57-58°C.

Embodiment 3

[0028] Add 2,3-heptadienoic acid ethyl ester (81.3mg, 0.52mmol), MeCN (4mL), water (0.27mL) in 25mL egg-shaped bottle, add iodine (129.2mg, 0.5mmol) under stirring, continue to The reaction was stirred at room temperature for 12 hours. The rest were the same as in Example 1, and 88.2 mg of the product 3-iodo-γ-heptenolactone was obtained with a yield of 66%. The product was a white solid with a melting point of 57-58°C.

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Abstract

This invention involves a synthetic method to a kind of beta-iodo-butenolide and its synthesizing method in which synthesizes-beta-Iodo-butenolide through the iodolactonization of 2, 3- joint alkene diethylene glycol dinitrate with iodine in the water-organic agents mixed solvent. At room temperature, in mixing solvent of water and organic agent, iodine takes cyclization with 2,3-allenic ester, receive beta-Iodo-butenolide. This method has advantage of mild reacting condition, short response time, high producing rate, low costs and easy industrialization.

Description

technical field [0001] The invention relates to a method for synthesizing β-iodobutenolide, in particular to a method for synthesizing β-iodobutenolide through iodine-participated 2,3-alkenate cyclization reaction. Background technique [0002] Five-membered ring unsaturated lactone is one of the most common structural units in natural products, which has many important physiological activities. For example: anti-bacterial and anti-inflammatory, anti-fungal, anti-tumor, and regulation of seed germination and plant growth, etc., which have great development and utilization value in medicine and pesticides. β-iodobutenolide is an extremely important intermediate in the synthesis of the above-mentioned physiologically active compounds. The traditional synthetic method of β-iodobutenolide is synthesized by the iodocyclization reaction of 2,3-alkenoic acid, as reported in the literature Tetrahedron Lett.1985, 26, 4811; Tetrahedron 1999, 55, 12137 A method for preparing β-iodobu...

Claims

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Application Information

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IPC IPC(8): C07D307/58
Inventor 麻生明傅春玲
Owner ZHEJIANG UNIV
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