Cactus alkaloids. XXVIII. .beta.-Phenethylamine and tetrahydroisoquinoline alkaloids from the Mexican cactus Dolichothele longimamma
Cactus alkaloids. XXVIII. .beta.-Phenethylamine and tetrahydroisoquinoline alkaloids from the Mexican cactus Dolichothele longimamma
复制标题
仙人掌生物碱。
DOI：
10.1021/jo00864a030
复制
发表时间：
1976
影响因子：
3.6
通讯作者：
J. McLaughlin
中科院分区：
文献类型：
--
作者：
R. L. Ranieri;J. McLaughlin
通过 PLC 从酚类馏分中分离出 10，为油状物：[a] D-36 (c 0.05)； NMR 2.42(s,3,1NMe)、3.77(s,3,1OMe)、5.90(br,2H,2OH)、6.52(s,1H)、6.29(s,1)、6.60(d,J=8Hz,2)、6.90(d,J=8Hz,2H);质谱m/e（相对强度）299（M+，1）、192（100）、107（9）。 10 的IR (CHCl3) 和NMR 谱与其对映异构体的真实样品相同。用乙醚重氮乙烷处理部分酚级分(20 mg)。 2天后以常规方式进行后处理，得到浅黄色油状的0,O'-二乙基-N-甲基乌药碱(11, 17 mg)。将其转化为草酸盐，从乙醇-乙醚中结晶为针状：mp 172-174；[]-114(c 0.05)(lit.11mp 173-174，[Ŧ]d-123)；质谱 m/e（相对强度）355（M+，1）、220（100）、135（11）。该化合物的红外光谱、混合物熔点、旋光度和 Rf 与真实样品相同。
From the phenolic fraction, 10 was isolated by PLC as an oil:[a] D-36 (c 0.05); NMR 2.42 (s, 3, 1 NMe), 3.77 (s, 3, 1 OMe), 5.90 (br, 2 H, 2 OH), 6.52 (s, 1 H), 6.29 (s, 1), 6.60 (d, J= 8 Hz, 2), 6.90 (d, J= 8 Hz, 2 H); mass spectrum m/e (rel intensity) 299 (M+, 1), 192 (100), 107 (9). The ir (CHC13) and NMR spectra of 10 were identical with those of an authentic sample of its en-antiomer.A portion of the phenolic fraction (20 mg) was treated with ethereal diazoethane. Work-up in the usual manner after 2 days yield-ed 0, O'-diethyl-N-methylcoclaurine (11, 17 mg) as a pale yellow oil. It was converted to the oxalate which crystallized from ethanol-ether as needles: mp 172-174;[]—114 (c 0.05)(lit. 11mp 173-174,[Ŧ] d—123); mass spectrum m/e (rel intensity) 355 (M+, 1), 220 (100), 135 (11). The ir spectrum, mixture melting point, op-tical rotation, and Rf of this compound were identical with those of an authentic sample.