Biphenyltetrols and Dibenzofuranones from Oxidative Coupling of Resorcinols with 4-Alkylpyrocatechols: New Ciues to the Mechanism of Insect Cuticle Sclerotization
作者:Merle Miessner、Orlando Crescenzi、Alessandra Napolitano、Giuseppe Prota、Svend Olav Andersen、Martin G. Peter
DOI:10.1002/hlca.19910740607
日期:1991.9.18
Oxidation of 4-alkylpyrocatechols 2 by means of an insect diphenoloxidase (laccase) or K3 [Fe(CN)6] yields, in the presence of resorcinols 1 (R2 H), complex mixtures of products from which biphenyltetrols 3 (R3 H) and dibenzofuranones 5 and 6 were isolated. It is suggested that similar homo-coupling products are formed from pyrocatechols 2b and 2c in insects during cuticle sclerotization.
在间苯二酚1(R 2 H)的存在下,通过昆虫二酚氧化酶(漆酶)或K 3 [Fe(CN)6 ]氧化4-烷基邻苯二酚2会生成复杂的产物混合物,其中联苯四酚3(R 3 H)和二苯并呋喃酮5和6被分离。建议在角质层硬化过程中由邻苯二酚2b和2c在昆虫中形成相似的均偶联产物。