Iriye R, Nakamura A, Takeshita M
Department of Bioscience and Biotechnology, Faculty of Agriculture, Shinshu University, Nagano, Japan.
Biosci Biotechnol Biochem. 1995 Mar;59(3):401-7. doi: 10.1271/bbb.59.401.
2-(2-Hydroxyalkylidene)cyclopentanones (1) and 5-(2-hydroxyoctylidene)-2-cyclopentenone (2) were synthesized by the aldol reaction of cyclopentanone-enolate (3)/cyclopentenone-enolate (19) with 2-bromoalkanals (4)/2-bromooctanal (4c) and subsequent treatment of the products with sodium acetate. The stereochemistry of the condensation, substitution and elimination was elucidated. The bio-antimutagenic activity of 1 increased as the 2-hydroxyalkylidene group increased in length up to = CHCH(OH)C8H17.
通过环戊酮烯醇盐（3）/环戊烯酮烯醇盐（19）与2-溴代醛（4）/2-溴代辛醛（4c）的羟醛反应，随后用乙酸钠处理产物，合成了2-（2-羟基亚烷基）环戊酮（1）和5-（2-羟基亚辛基）-2-环戊烯酮（2）。阐明了缩合、取代和消除反应的立体化学。随着2-羟基亚烷基的长度增加至= CHCH(OH)C8H17，1的生物抗诱变活性增强。
