(3aR,9aR)-3a-benzyl-1-(4-chlorophenylsulfonyl)-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]indole | 1252671-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (3aR,9aR)-3a-benzyl-1-(4-chlorophenylsulfonyl)-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]indole
• 英文别名: (3aR,9aR)-3a-benzyl-1-(4-chlorophenyl)sulfonyl-3,4,9,9a-tetrahydro-2H-benzo[f]indole
• CAS: 1252671-14-9
• 化学式: C₂₅H₂₄ClNO₂S
• 分子量: 437.99
• InChiKey: XVPACLNXIRINIZ-JWQCQUIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-chloro-N-(3,3-dibenzylpent-4-enyl)benzenesulfonamide 在 manganese(IV) oxide 、 copper(II) bis(trifluoromethanesulfonate) 、 potassium carbonate 、 (R,R)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 作用下， 以 三氟甲苯 为溶剂， 反应 24.0h， 以99%的产率得到(3aR,9aR)-3a-benzyl-1-(4-chlorophenylsulfonyl)-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]indole
  参考文献：
  名称：

  Diastereo- and Enantioselective Copper-Catalyzed Intramolecular Carboamination of Alkenes for the Synthesis of Hexahydro-1H-benz[f]indoles

  摘要：

  A new method for the enantioselective synthesis of hexahydro-1H-benz[f]indoles is described. This copper-catalyzed enantioselective intramolecular alkene carboamination process can install vicinal tertiary and quaternary carbon stereocenters with high levels of diastereo- and enantioselectivity. The C-C bond-forming component of the reaction constitutes a C-H functionalization and no electronic activation of the aryl ring that undergoes addition is required. A known 5-HT1A receptor antagonist was synthesized efficiently using this method.

  DOI：

  10.1021/ol102233g

文献信息

• Diastereo- and Enantioselective Copper-Catalyzed Intramolecular Carboamination of Alkenes for the Synthesis of Hexahydro-1<i>H</i>-benz[<i>f</i>]indoles
  作者：Lei Miao、Imranul Haque、Maria R. Manzoni、Weng Siong Tham、Sherry R. Chemler

  DOI：10.1021/ol102233g

  日期：2010.11.5

  A new method for the enantioselective synthesis of hexahydro-1H-benz[f]indoles is described. This copper-catalyzed enantioselective intramolecular alkene carboamination process can install vicinal tertiary and quaternary carbon stereocenters with high levels of diastereo- and enantioselectivity. The C-C bond-forming component of the reaction constitutes a C-H functionalization and no electronic activation of the aryl ring that undergoes addition is required. A known 5-HT1A receptor antagonist was synthesized efficiently using this method.