(8R,13S,14S)-3-Methoxy-13-((S)-toluene-4-sulfinyl)-6,7,8,12,13,14,15,16-octahydro-cyclopenta[a]phenanthren-17-one | 160855-30-1

• 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: (8R,13S,14S)-3-Methoxy-13-((S)-toluene-4-sulfinyl)-6,7,8,12,13,14,15,16-octahydro-cyclopenta[a]phenanthren-17-one
• 英文别名: (8R,13S,14S)-3-methoxy-13-[(S)-(4-methylphenyl)sulfinyl]-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 160855-30-1
• 化学式: C₂₅H₂₆O₃S
• 分子量: 406.546
• InChiKey: IHOBXNOWRQTHOG-TYIRCOKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8R,13S,14S)-3-Methoxy-13-((S)-toluene-4-sulfinyl)-6,7,8,12,13,14,15,16-octahydro-cyclopenta[a]phenanthren-17-one 在 aluminum amalgam 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以52%的产率得到(8R,13R,14S)-3-Methoxy-6,7,8,12,13,14,15,16-octahydro-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
• 作为产物：
  描述：

  7-甲氧基-4-乙烯基-1,2-二氢萘 、 (S)-(+)-2-(p-tolylsulfinyl)-2-cyclopentenone 在 二氯乙基铝 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到(8R,13S,14S)-3-Methoxy-13-((S)-toluene-4-sulfinyl)-6,7,8,12,13,14,15,16-octahydro-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