5,6-epoxy-β-sitosterol | 87303-93-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 5,6-epoxy-β-sitosterol
• 英文别名: sitosterol epoxide；5α,6α- and 5β,6β-Epoxystigmastan-3β-ol；(1S,2R,5S,11S,12S,15R,16R)-15-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-ol
• CAS: 87303-93-3
• 化学式: C₂₉H₅₀O₂
• 分子量: 430.715
• InChiKey: ZBNPKSZFWFSSQK-PZVPXVPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6-epoxy-β-sitosterol 在 chromium(VI) oxide 、 盐酸 、 三氟化硼乙醚 、 氢氟酸 、 magnesium sulfate 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 、 丙酮 、 苯 为溶剂， 反应 3.0h， 生成 6α-fluorostigmast-4-en-3-one
  参考文献：
  名称：

  Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach

  摘要：

  Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5 beta-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5 beta-cholestane skeleton, 1b with the 5 beta-androstane skeleton, Ic with a fluorine substituent instead of the chlorine and Id with a beta-D-galactopyranose instead of the beta-D-glucopyranose of the original pheromone. Their bioassay shows that la and Ic are active, while Ib and Id are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00018-1
• 作为产物：
  描述：

  植物甾醇 在 magnesium bis(monoperoxyphthalate)hexahydrate 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 5,6-epoxy-β-sitosterol
  参考文献：
  名称：

  Efficient trans-diaxial hydroxylation of Δ5-steroids

  摘要：

  A convenient, fast, and high-yielding process to synthesize 5 alpha,6 beta-dihydroxysteroids directly from the correspondent Delta(5)-steroids is reported. The reaction protocol consists in the conjugation of a readily available and stable oxidant, magnesium bis(monoperoxyphthalate) hexahydrate, with the non-toxic bismuth(III) triflate in acetone to afford the trans-diaxial hydroxylation product in a stepwise manner and in excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.089

文献信息

• Mori, Kenji; Fukamatsu, Kunio; Kido, Masaru, Liebigs Annalen der Chemie, 1993, # 6, p. 665 - 670
  作者：Mori, Kenji、Fukamatsu, Kunio、Kido, Masaru

  DOI：——

  日期：——