(2R,3S,3aR,9bR)-tert-butyl 3-phenyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[g]indole-2-carboxylate | 1373520-38-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S,3aR,9bR)-tert-butyl 3-phenyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[g]indole-2-carboxylate
• 英文别名: tert-butyl (2R,3S,3aR,9bR)-3-phenyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[g]indole-2-carboxylate
• CAS: 1373520-38-7
• 化学式: C₂₃H₂₇NO₂
• 分子量: 349.473
• InChiKey: SHSRDUCVRDMUJC-MXEMCNAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,3aR,9bR)-tert-butyl 3-phenyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[g]indole-2-carboxylate 、 4-溴苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以94%的产率得到(2R,3S,3aR,9bR)-tert-butyl 1-(4-bromobenzoyl)-3-phenyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[g]indole-2-carboxylate
  参考文献：
  名称：

  Asymmetric Phase-Transfer-Catalyzed Conjugate Addition of Glycine Imine to Exocyclic α,β-Unsaturated Ketones: Construction of Polycyclic Imines Containing Three Stereocenters

  摘要：

  We developed a facile, one-pot, multistep transformation between glycine imine and exocyclic alpha,beta-unsaturated ketones in reactions catalyzed by chiral phase-transfer catalysts (PTC). A series of polycyclic imines containing three adjacent stereocenters were obtained in good to high yields with high diastereo- and enantioselectivities. Further transformation of the imines could afford N-fused polycyclic compounds with four adjacent stereocenters.

  DOI：

  10.1021/jo300500r
• 作为产物：
  描述：

  (E)-2-benzylidene-1-tetralone 在 C₇₀H₄₀F₂₄NO⁽¹⁺⁾*Br^(1-) 、 caesium carbonate 、 锌 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 103.5h， 生成 (2R,3S,3aR,9bR)-tert-butyl 3-phenyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[g]indole-2-carboxylate
  参考文献：
  名称：

  Asymmetric Phase-Transfer-Catalyzed Conjugate Addition of Glycine Imine to Exocyclic α,β-Unsaturated Ketones: Construction of Polycyclic Imines Containing Three Stereocenters

  摘要：

  We developed a facile, one-pot, multistep transformation between glycine imine and exocyclic alpha,beta-unsaturated ketones in reactions catalyzed by chiral phase-transfer catalysts (PTC). A series of polycyclic imines containing three adjacent stereocenters were obtained in good to high yields with high diastereo- and enantioselectivities. Further transformation of the imines could afford N-fused polycyclic compounds with four adjacent stereocenters.

  DOI：

  10.1021/jo300500r

文献信息

• Asymmetric Phase-Transfer-Catalyzed Conjugate Addition of Glycine Imine to Exocyclic α,β-Unsaturated Ketones: Construction of Polycyclic Imines Containing Three Stereocenters
  作者：Jing Nie、Ming-Qing Hua、Heng-Ying Xiong、Yan Zheng、Jun-An Ma

  DOI：10.1021/jo300500r

  日期：2012.5.4

  We developed a facile, one-pot, multistep transformation between glycine imine and exocyclic alpha,beta-unsaturated ketones in reactions catalyzed by chiral phase-transfer catalysts (PTC). A series of polycyclic imines containing three adjacent stereocenters were obtained in good to high yields with high diastereo- and enantioselectivities. Further transformation of the imines could afford N-fused polycyclic compounds with four adjacent stereocenters.