dimethyl (3S,4S)-4-ethylspiro[cyclopentane-3,3'-indole]-1,1-dicarboxylate | 1443529-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: dimethyl (3S,4S)-4-ethylspiro[cyclopentane-3,3'-indole]-1,1-dicarboxylate
• CAS: 1443529-03-0
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: KDCDHSCTNITWPK-SGTLLEGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 正丙胺 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 caesium carbonate 、 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 、 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以75%的产率得到
  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