4α,3β-(3'-oxocyclohexano)-5β-cholestane | 943341-76-2

• 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: 4α,3β-(3'-oxocyclohexano)-5β-cholestane
• 英文别名: 4alpha,3beta-(3'-Oxocyclohexano)-5beta-cholestane；(3R,3aR,5aS,5bS,7aS,11aS,11bR,13aS,13bS)-3a,5b-dimethyl-3-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,5a,6,7,7a,8,10,11,11a,11b,12,13,13a,13b-octadecahydrocyclopenta[a]chrysen-9-one
• CAS: 943341-76-2
• 化学式: C₃₁H₅₂O
• 分子量: 440.753
• InChiKey: UMOIFNKTUYALEM-HNBFZDDTSA-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：

  4α,3β-(3'-oxocyclohexano)-5β-cholestane 在 四氯化钛 、 zinc(II) chloride 作用下， 以 正己烷 为溶剂， 以47%的产率得到(4S,5R,8S,9S,12R,13R,16S,17S,20S,25S,26R,29S,30S,33R,34R,37S,38S,41S,46S,47R,50S,51S,54R,55R,58S,59S,62S)-13,17,34,38,55,59-hexamethyl-12,33,54-tris[(2R)-6-methylheptan-2-yl]hexadecacyclo[42.19.0.02,22.04,20.05,17.08,16.09,13.023,43.025,41.026,38.029,37.030,34.046,62.047,59.050,58.051,55]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 盐酸 、 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4α,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