2α,3β-(3'-oxocyclohexano)-5β-cholestane | 3908-44-9

• 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: 2α,3β-(3'-oxocyclohexano)-5β-cholestane
• 英文别名: 2α,3β,3',4',5',6'-Hexahydro-benz<2,3>-5β-cholestan-4'-on；2alpha,3beta-(3'-Oxocyclohexano)-5beta-cholestane；(1S,2S,5R,6R,9S,10R,13R,15R,20S)-1,5-dimethyl-6-[(2R)-6-methylheptan-2-yl]pentacyclo[11.8.0.02,10.05,9.015,20]henicosan-17-one
• CAS: 3908-44-9
• 化学式: C₃₁H₅₂O
• 分子量: 440.753
• InChiKey: KWRBEYFEPOYBST-QIHVKESBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2α,3β-(3'-oxocyclohexano)-5β-cholestane 在 四氯化钛 、 zinc(II) chloride 作用下， 以 正己烷 为溶剂， 以18%的产率得到(4R,6S,7S,10R,11R,14S,15R,18R,20R,25R,27S,28S,31R,32R,35S,36R,39R,41R,46R,48S,49S,52R,53R,56S,57R,60R,62R)-6,10,27,31,48,52-hexamethyl-11,32,53-tris[(2R)-6-methylheptan-2-yl]hexadecacyclo[42.19.0.02,22.04,20.06,18.07,15.010,14.023,43.025,41.027,39.028,36.031,35.046,62.048,60.049,57.052,56]trihexaconta-1,22,43-triene
  参考文献：
  名称：

  The Supertristeroids:  Large, Chiral, Molecular Bowls Prepared by Trimerization of Pentacyclic Steroidal Ketones

  摘要：

  Robinson annulation of coprostanone (1) at the 2,3- and 3,4-positions gave two pentacyclic enones (7 and 10) that contain A/B-cis-fused ring junctions. Reduction of these enones gave the pentacyclic steroidal ketones 2 alpha,3 beta- (8) and 2 alpha,3 alpha-(3'-oxocyclohexano)-5 beta-cholestane (9) and 4 alpha,3 beta- (11) and 4 alpha,3 alpha-(3'-oxocyclohexano)-5 beta-cholestane (12). The structures of compounds 8, 9, and 11 were unambiguously established by X-ray analysis. TiCl4-promoted trimerization of compounds 8 and 11 gave the "supertristeroids" 4 and 5, respectively: large (C-93) chiral, hydrocarbon clefts with C-3-symmetric pockets approximately 12 angstrom in diameter.

  DOI：

  10.1021/jo070458k
• 作为产物：
  描述：

  在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 2α,3β-(3'-oxocyclohexano)-5β-cholestane
  参考文献：
  名称：

  The Supertristeroids:  Large, Chiral, Molecular Bowls Prepared by Trimerization of Pentacyclic Steroidal Ketones

  摘要：

  Robinson annulation of coprostanone (1) at the 2,3- and 3,4-positions gave two pentacyclic enones (7 and 10) that contain A/B-cis-fused ring junctions. Reduction of these enones gave the pentacyclic steroidal ketones 2 alpha,3 beta- (8) and 2 alpha,3 alpha-(3'-oxocyclohexano)-5 beta-cholestane (9) and 4 alpha,3 beta- (11) and 4 alpha,3 alpha-(3'-oxocyclohexano)-5 beta-cholestane (12). The structures of compounds 8, 9, and 11 were unambiguously established by X-ray analysis. TiCl4-promoted trimerization of compounds 8 and 11 gave the "supertristeroids" 4 and 5, respectively: large (C-93) chiral, hydrocarbon clefts with C-3-symmetric pockets approximately 12 angstrom in diameter.

  DOI：

  10.1021/jo070458k

文献信息

• Bloch,J.-C.; Ourisson,G., Bulletin de la Societe Chimique de France, 1964, p. 3018 - 3030
  作者：Bloch,J.-C.、Ourisson,G.

  DOI：——

  日期：——