3-Methoxy-6,7,11,12,15,16-hexahydro-cyclopenta[a]phenanthren-17-one | 21070-86-0

• 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: 3-Methoxy-6,7,11,12,15,16-hexahydro-cyclopenta[a]phenanthren-17-one
• 英文别名: 3-Methoxygona-1(10),2,4,8,13-pentaen-17-one；3-methoxy-6,7,11,12,15,16-hexahydrocyclopenta[a]phenanthren-17-one
• CAS: 21070-86-0
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: ZJDQUESRTUGPHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-Methoxy-13-(toluene-4-sulfinyl)-6,7,8,12,13,14,15,16-octahydro-cyclopenta[a]phenanthren-17-one 在 calcium carbonate 作用下， 以58%的产率得到3-Methoxy-6,7,8,12,15,16-hexahydro-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene: an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes

  摘要：

  The reactions of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene catalyzed by EtAlCl(2) yields adducts easily desulfinylated into optically pure perhydro-cyclopenta[a]phenanthrenes. The endo- (controlled by CO group) and regio- (controlled by the substituent at C-2 of diene) selectivities of the asymmetric Diels-Alder reaction are complete. The pi-facial selectivity is also very high and dependent on both the sulfinyl configuration and the amount of EtAlCL(2) used.

  DOI：

  10.1016/s0040-4039(00)78571-6

文献信息

• Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene: an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes
  作者：Inés Alonso、Juan C. Carretero、José L. García Ruano、Luisa M. Martín Cabrejas、Isabel López-Solera、Paul R. Raithby

  DOI：10.1016/s0040-4039(00)78571-6

  日期：1994.12

  The reactions of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene catalyzed by EtAlCl(2) yields adducts easily desulfinylated into optically pure perhydro-cyclopenta[a]phenanthrenes. The endo- (controlled by CO group) and regio- (controlled by the substituent at C-2 of diene) selectivities of the asymmetric Diels-Alder reaction are complete. The pi-facial selectivity is also very high and dependent on both the sulfinyl configuration and the amount of EtAlCL(2) used.