3β-hydroxy-5,6β-cyclopropano-5β-cholestane | 38037-44-4

• 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: 3β-hydroxy-5,6β-cyclopropano-5β-cholestane
• 英文别名: 3β-Hydroxy-5,7α-cyclo-B-homo-5α-cholestan；5,7α-Cyclo-B-homo-5α-cholestan-3β-ol；(1S,2R,5S,7S,9S,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]pentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-ol
• CAS: 38037-44-4
• 化学式: C₂₈H₄₈O
• 分子量: 400.689
• InChiKey: QGHUEYAIOHJWEJ-KKUGEXSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-5,6β-cyclopropano-5β-cholestane 在 吡啶 、 potassium acetate 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 生成 5,7α-Cyclo-B-homo-5α-cholest-3-en
  参考文献：
  名称：

  Kohout,L.; Fajkos,J., Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 913 - 928

  摘要：

  DOI：
• 作为产物：
  描述：

  Methanesulfonic acid (3S,5S,6S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopropa[5,6]cyclopenta[a]phenanthren-3-yl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 3β-hydroxy-5,6β-cyclopropano-5β-cholestane
  参考文献：
  名称：

  Kohout,L.; Fajkos,J., Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 913 - 928

  摘要：

  DOI：

文献信息

• Simmons-Smith methylenation of the 5,6-double bond in 19-hydroxylated steroids
  作者：Jan Fajkoš、Jiří Joska

  DOI：10.1135/cccc19790251

  日期：——

  Simmons-Smith methylenation of 5-cholestene-3β,19-diol 3-monoacetate has been studied and structure of the products established by spectral and chemical means.

  对5-胆甾烯-3β,19-二醇3-单乙酸酯进行了Simmons-Smith亚甲基化反应的研究，并通过光谱和化学手段确定了产物的结构。
• Sheikh,Y.M. et al., Journal of the Chemical Society. Perkin transactions I, 1974, p. 909 - 914
  作者：Sheikh,Y.M. et al.

  DOI：——

  日期：——
• Microbial transformation of 3-hydroxy-5,6-cyclopropanocholestanes - An alternative route to 6-methylsteroids
  作者：Jiann-Long Yan、Shoei-Sheng Lee、K.C. Wang

  DOI：10.1016/s0039-128x(00)00170-7

  日期：2000.12

  Incubation of 3 beta -hydroxy-5,6 beta alpha cyclopropano-5 alpha -cholestane (4), 3 beta -hydroxy-5,6 beta -cyclopropano-5 beta -cholestane (5), and 3 beta -hydroxy-5,6 alpha -cyclopropano-5 alpha -cholest-7-ene (6) with Mycobacterium sp. (NRRL B-3805) gave a mixture of side chain cleaved 17-keto steroids as the major products in 52, 57, and 69% yields, respectively. Among these 17-keto steroids, the cyclopropyl ring eliminated product, androst-4-ene-3,17-dione (9), was isolated in 6, 4, and 8% yields, respectively. A cyclopropyl ring migration product, 6 alpha ,7 alpha -cyclopro-panoandrost-4-ene-3,17-dione (16), was isolated from the incubation mixture of 6 in 4% yield, also 10% yield of 16 was obtained when 5,6 alpha -cyclopropano-5 alpha -androst-7-ene-3, 17-dione (12) was incubated. The cyclopropyl ring opening and subsequent reduction followed by oxidation of the two major biotransformation products, 5,6 beta -cyclopropano-5 beta -androsta-3, 17-dione (10) and 5,6 alpha -cyclopropano-5 alpha -androsta-3,17-dione (7), gave 6 beta- and 6 alpha -methylandrost-4-ene-3,17-dione in 60, and 45% yields, respectively. (C) 2000 Elsevier Science Inc. All rights reserved.
• Kohout,L.; Fajkos,J., Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 3490 - 3500
  作者：Kohout,L.、Fajkos,J.

  DOI：——

  日期：——