3β-hydroxy-5,6α-cyclopropano-5α-cholestane | 35339-47-0

• 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-5,6α-cyclopropano-5α-cholestane
• 英文别名: 5α,6α-cyclopropa<5,6>cholestan-3β-ol；3β-Hydroxy-5α,6-cyclopropano-5α-cholestan；3β-Hydroxy-5,6α-cyclopropano-5α-cholestan；3β-Hydroxy-5,7β-cyclo-B-homo-5β-cholestan；(1S,2R,5S,7R,9R,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: 35339-47-0
• 化学式: C₂₈H₄₈O
• 分子量: 400.689
• InChiKey: QGHUEYAIOHJWEJ-GMYIAEGMSA-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-5,6α-cyclopropano-5α-cholestane 在 Mycobacterium sp. (NRRL B-3805) 、 Nutrient broth-dextrose medium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 264.0h， 生成 雄烯二酮
  参考文献：
  名称：

  Microbial transformation of 3-hydroxy-5,6-cyclopropanocholestanes - An alternative route to 6-methylsteroids

  摘要：

  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.

  DOI：

  10.1016/s0039-128x(00)00170-7
• 作为产物：
  描述：

  3β-acetoxycholest-5-en-7-ol 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 锌铜偶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.33h， 生成 3β-hydroxy-5,6α-cyclopropano-5α-cholestane
  参考文献：
  名称：

  Brown, Linda; Lyall, William J. S.; Suckling, Colin J., Journal of the Chemical Society. Perkin transactions I, 1987, p. 595 - 600

  摘要：

  DOI：

文献信息

• The Effect of Some 3-Oxygen Functions on the Simmons–Smith Methylenation of 5,6-Unsaturated Steroids
  作者：J. F. Templeton、C. W. Wie

  DOI：10.1139/v71-608

  日期：1971.11.15

  The effect of 3α- and 3β-hydroxy, 3α- and 3β-acetoxy, 3-ethylene acetal, and 3α-methoxy derivatives of 5-cholestene on the addition of the Simmons–Smith reagent to the steroidal 5,6-double bond has been investigated. Reaction occurred only with epi-cholesterol to yield chiefly 3α-hydroxy-5,6α-cyclopropano-5α-cholestane. The 3α-ethyl ether, 3α-acetate, and a dialkoxymethane have been identified as byproducts

  5-胆甾烯的 3α-和 3β-羟基、3α-和 3β-乙酰氧基、3-乙缩醛和 3α-甲氧基衍生物对 Simmons-Smith 试剂加成到甾体 5,6-双键的影响有被调查。仅与表胆固醇发生反应，主要生成 3α-羟基-5,6α-环丙烷-5α-胆甾烷。3α-乙醚、3α-乙酸酯和二烷氧基甲烷已被鉴定为副产物。给出了 pmr 和质谱数据。
• Mass Spectra of some 5,6α-Cyclopropano-5α-cholestane Derivatives
  作者：J. F. Templeton、C. W. Wie

  DOI：10.1139/v74-081

  日期：1974.2.1

  The mass spectra of the epimeric 3-substituted hydroxy and ethoxy derivatives of 5,6α-cyclopropano-5α-cholestane have been reported and on the basis of deuterium-labelled compounds the nature of some high molecular weight fragments are discussed. Together with the characteristic fragment ions of steroidal derivatives ions related to the presence of the 5,6α-cyclopropane ring occur at m/e 247, 301, 302, and 329.

  报道了5,6α-环丙烷-5α-胆甾烷的外消旋3-取代羟基和乙氧基衍生物的质谱，并基于氘标记化合物讨论了一些高分子量碎片的性质。除了类固醇衍生物的特征碎片离子外，与5,6α-环丙烷环存在相关的离子出现在m/e 247、301、302和329处。
• Kohout,L., Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 2760 - 2767
  作者：Kohout,L.

  DOI：——

  日期：——
• Kohout,L.; Fajkos,J., Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 913 - 928
  作者：Kohout,L.、Fajkos,J.

  DOI：——

  日期：——
• Kohout,L.; Fajkos,J., Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 3490 - 3500
  作者：Kohout,L.、Fajkos,J.

  DOI：——

  日期：——