(1S,2S)-2-phenylspiro[cyclopentane-1,3'-indole] | 1429926-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1S,2S)-2-phenylspiro[cyclopentane-1,3'-indole]
• CAS: 1429926-44-2
• 化学式: C₁₈H₁₇N
• 分子量: 247.34
• InChiKey: VFCHDJCFJPWARI-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-phenylspiro[cyclopentane-1,3'-indole] 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以86%的产率得到(1S)-1-phenyl-2,3,4,9-tetrahydro-1H-carbazole
  参考文献：
  名称：

  A Combined Theoretical and Experimental Investigation into the Highly Stereoselective Migration of Spiroindolenines

  摘要：

  This paper describes a combined theoretical and experimental investigation into the acid-catalyzed migration of spiroindolenines to the corresponding fused cyclic products. It is suggested that the "three-center-two-electron"-type transition state is the crucial reason accounting for the highly stereoselective phenomenon. Further studies demonstrated that the electronic property of the migratory group as well as the ring size may have a major influence on the reaction profile of the migration process. Some predictions based on the computational results were supported by additional experiments.

  DOI：

  10.1021/jo400365e
• 作为产物：
  描述：

  4-(1H-indol-3-yl)-1-phenylbutan-1-one 在 lithium aluminium tetrahydride 、 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1S,2S)-2-phenylspiro[cyclopentane-1,3'-indole] 、
  参考文献：
  名称：

  A Combined Theoretical and Experimental Investigation into the Highly Stereoselective Migration of Spiroindolenines

  摘要：

  This paper describes a combined theoretical and experimental investigation into the acid-catalyzed migration of spiroindolenines to the corresponding fused cyclic products. It is suggested that the "three-center-two-electron"-type transition state is the crucial reason accounting for the highly stereoselective phenomenon. Further studies demonstrated that the electronic property of the migratory group as well as the ring size may have a major influence on the reaction profile of the migration process. Some predictions based on the computational results were supported by additional experiments.

  DOI：

  10.1021/jo400365e

文献信息

• A Combined Theoretical and Experimental Investigation into the Highly Stereoselective Migration of Spiroindolenines
  作者：Chao Zheng、Qing-Feng Wu、Shu-Li You

  DOI：10.1021/jo400365e

  日期：2013.5.3

  This paper describes a combined theoretical and experimental investigation into the acid-catalyzed migration of spiroindolenines to the corresponding fused cyclic products. It is suggested that the "three-center-two-electron"-type transition state is the crucial reason accounting for the highly stereoselective phenomenon. Further studies demonstrated that the electronic property of the migratory group as well as the ring size may have a major influence on the reaction profile of the migration process. Some predictions based on the computational results were supported by additional experiments.