ethyl 1,2,3,4,4a,6,7,8,9,9a-decahydropyrido[1,2-a]indole-10-carboxylate | 1193378-38-9

• 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: ethyl 1,2,3,4,4a,6,7,8,9,9a-decahydropyrido[1,2-a]indole-10-carboxylate
• 英文别名: ethyl (4aR,9aR)-1,2,3,4,4a,6,7,8,9,9a-decahydropyrido[1,2-a]indole-10-carboxylate
• CAS: 1193378-38-9
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: XGKQMUKCKUUGJF-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  trimethylsilyl (S)-piperidine-2-carboxylate 、 ethyl 8-oxooct-2-ynoate 以 甲苯 为溶剂， 反应 1.0h， 以79%的产率得到ethyl 1,2,3,4,4a,6,7,8,9,9a-decahydropyrido[1,2-a]indole-10-carboxylate
  参考文献：
  名称：

  An Efficient Synthetic Approach to Polycyclic 2,5-Dihydropyrroles from α-Silyloxy Ketones

  摘要：

  A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic gamma-sjlyloxy-beta-hydroxy-alpha-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.

  DOI：

  10.1021/jo901978y

文献信息

• An Efficient Synthetic Approach to Polycyclic 2,5-Dihydropyrroles from α-Silyloxy Ketones
  作者：Cristian Draghici、Qiufeng Huang、Matthias Brewer

  DOI：10.1021/jo901978y

  日期：2009.11.6

  A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic gamma-sjlyloxy-beta-hydroxy-alpha-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.