Insight into the chemistry of cycloaddition between α-ketol oxylipin and epinephrine: isolation and structure elucidation of a new reaction product

被引：3

作者：

Kai, Kenji ^{[1
]}

Oba, Yukie ^{[2
]}

Akaike, Ryota ^{[2
]}

Murata, Ariaki ^{[1
]}

Nishikawa, Toshio ^{[3
]}

Watanabe, Naoharu ^{[1
]}

机构：

[1] Shizuoka Univ, Grad Sch Sci & Technol, Suruga Ku, Shizuoka 4228529, Japan

[2] Shizuoka Univ, Fac Agr, Suruga Ku, Shizuoka 4228529, Japan

[3] Nagoya Univ, Grad Sch Bioagr Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 18期

关键词：

Cycloaddition; Reaction mechanism; (12Z,15Z)-9-Hydroxy-10-oxooctadeca-12,15-dienoic acid; Oxylipin; Epinephrine; LEMNA-PAUCICOSTATA; LINOLENIC ACID; FN;

D O I：

10.1016/j.tetlet.2013.02.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alpha-ketol oxylipin (12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid (1) reacts with epinephrine (2) to afford unique cycloadducts, KE1 (3) and KE2 (4), both of which strongly induce flowering in Lemna paucicostata. Here we isolate compound 5 from the reaction mixture and identify it as a Michael-type adduct of 1 with adrenochrome (6), an oxidized form of 2. Compound 5 was gradually converted into KEs in aqueous solution, suggesting that the compound is an intermediate of KEs. From these results, we newly propose the reaction mechanism of the cycloaddition between 1 and 2. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2247 / 2250

页数：4

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