5,6-bis(4-cyanophenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one | 1192648-74-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5,6-bis(4-cyanophenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one
• 英文别名: 4-[(8aR)-5-(4-cyanophenyl)-7-oxo-2,3,8,8a-tetrahydro-1H-indolizin-6-yl]benzonitrile
• CAS: 1192648-74-0
• 化学式: C₂₂H₁₇N₃O
• 分子量: 339.396
• InChiKey: NUXHZWUNTGTHAY-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,4’-二氰基二苯乙烯 、 5-isocyanatopent-1-ene 在 烟酸甲酯 、 chlorobis(ethylene)rhodium(I) dimer 、 O,O'-[(R)-3,3'-bis(trimethylsilyl)-1,1'-binaphthyl-2,2'-diyl]-N,N-dimethylphosphoramidite 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 5,6-bis(4-cyanophenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one 、 5,6-bis(4-cyanophenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one
  参考文献：
  名称：

  Excess Substrate is a Spectator Ligand in a Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of Alkenyl Isocyanates with Tolanes

  摘要：

  Excess substrate has been identified as an unintended spectator ligand affecting enantioselectivity in the [2 + 2 + 2] cycloaddition of alkenyl isocyanates with tolanes. Replacement of excess substrate with an exogenous additive affords products with consistent and higher ee's. The increase in enantioselectivity is the result of a change in composition of a proposed rhodium(III) intermediate on the catalytic cycle. The net result is a rational probe of a short-lived rhodium(III) intermediate and gives insight that may have applications in many rhodium-catalyzed reactions.

  DOI：

  10.1021/ol9020805

文献信息

• Excess Substrate is a Spectator Ligand in a Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of Alkenyl Isocyanates with Tolanes
  作者：Mark Emil Oinen、Robert T. Yu、Tomislav Rovis

  DOI：10.1021/ol9020805

  日期：2009.11.5

  Excess substrate has been identified as an unintended spectator ligand affecting enantioselectivity in the [2 + 2 + 2] cycloaddition of alkenyl isocyanates with tolanes. Replacement of excess substrate with an exogenous additive affords products with consistent and higher ee's. The increase in enantioselectivity is the result of a change in composition of a proposed rhodium(III) intermediate on the catalytic cycle. The net result is a rational probe of a short-lived rhodium(III) intermediate and gives insight that may have applications in many rhodium-catalyzed reactions.