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Synthesis of butenolides by reactions of 3‐alkenoic acids with diphenyl sulfoxide/oxalyl chloride
Flavour and Fragrance Journal ( IF 2.6 ) Pub Date : 2018-08-09 , DOI: 10.1002/ffj.3464
Rui Ding 1 , Yaxi Li 1 , Yongguo Liu 1 , Baoguo Sun 1 , Shaoxiang Yang 1 , Hongyu Tian 1
Affiliation  

Butenolides are of high interest as potential flavouring compounds. Efficient and general methods for the production of these compounds remain to be developed. A series of butenolides were prepared starting from 3‐alkenoic acids with diphenyl sulfoxide/oxalyl chloride, followed by treatment with bases. The 3‐alkenoic acids with alkyl substitutents on the double bond were converted into the corresponding 2‐butenolides with yields of greater than 77%, whereas those with aryl groups on the double bond produced the corresponding 3‐butenolides with yields of about 80%. The butenolides were produced by β eliminations of the corresponding chlorolactones, which were generated from the chlorolactonization of 3‐alkenoic acids. The chlorodiphenylsulfonium salt produced from the reaction between diphenyl sulfoxide and oxalyl chloride was supposed to be the chlorinating reagent for the chlorolactonization. This is a very simple and convenient method for the preparation of butenolides.

中文翻译:

3-链烯酸与二苯亚砜/草酰氯的反应合成丁烯内酯

丁烯内酯作为潜在的调味化合物备受关注。生产这些化合物的有效和通用方法仍有待开发。从3-链烯酸与二苯亚砜/草酰氯开始,制备一系列丁烯内酯,然后用碱处理。双键上带有烷基取代基的3-链烯酸被转化为相应的2-丁烯酸内酯,产率高于77%,而双键上带有芳基的3-烯酸产生了相应的3-丁烯内酯,产率约为80%。丁烯内酯是由β产生的消除了相应的氯代内酯,后者是由3-链烯酸的氯代内酯化作用产生的。由二苯基亚砜与草酰氯之间的反应产生的氯二苯基s盐被认为是用于氯内酯化的氯化试剂。这是制备丁烯内酯的非常简单方便的方法。
更新日期:2018-08-09
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