(6aS,14aS,14bR)-6a-methyl-1,5,6,6a,13,14,14a,14b-octahydronaphtho[2,1-f]pyrrolo[2,1-a]isoquinolin-3(2H)-one | 1222922-89-5

• 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: (6aS,14aS,14bR)-6a-methyl-1,5,6,6a,13,14,14a,14b-octahydronaphtho[2,1-f]pyrrolo[2,1-a]isoquinolin-3(2H)-one
• 英文别名: (6aS,14aR,14bS)-6a-methyl-1,2,5,6,13,14,14a,14b-octahydrophenanthro[1,2-g]indolizin-3-one
• CAS: 1222922-89-5
• 化学式: C₂₁H₂₃NO
• 分子量: 305.42
• InChiKey: UCIHFZFGBBCWQK-IRFCIJBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-5-hydroxy-1-(3-methyl-6-(naphthalen-1-yl)hex-3-en-1-yl)pyrrolidin-2-one 在 盐酸 、 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-3,3-dimethyl-1-oxo-1-((R)-2-(pyren-4-yl)pyrrolidin-1-yl)butan-2-yl)thiourea 作用下， 以 乙醚 、 甲基叔丁基醚 为溶剂， 以75%的产率得到(6aS,14aS,14bR)-6a-methyl-1,5,6,6a,13,14,14a,14b-octahydronaphtho[2,1-f]pyrrolo[2,1-a]isoquinolin-3(2H)-one
  参考文献：
  名称：

  Enantioselective Thiourea-Catalyzed Cationic Polycyclizations

  摘要：

  A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation-Pi interactions are a principal determinant of enantioselectivity.

  DOI：

  10.1021/ja101256v

文献信息

• Enantioselective Thiourea-Catalyzed Cationic Polycyclizations
  作者：Robert R. Knowles、Song Lin、Eric N. Jacobsen

  DOI：10.1021/ja101256v

  日期：2010.4.14

  A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation-Pi interactions are a principal determinant of enantioselectivity.