(2-hydroxy-3,3a,4,5,6,7-hexahydro-2H-inden-1-yl)-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone | 439807-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2-hydroxy-3,3a,4,5,6,7-hexahydro-2H-inden-1-yl)-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone
• CAS: 439807-54-2
• 化学式: C₁₆H₂₅NO₃
• 分子量: 279.379
• InChiKey: CPNJNGUMNYFRHO-LXVYMNJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-hydroxy-3,3a,4,5,6,7-hexahydro-2H-inden-1-yl)-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.0h， 以73%的产率得到[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-(4,5,6,7-tetrahydro-2H-inden-1-yl)methanone
  参考文献：
  名称：

  An intramolecular Pauson–Khand approach to the synthesis of chiral cyclopentadienes

  摘要：

  A procedure for the synthesis of chirally-substituted cyclopentadienes has been developed by employing the intramolecular Pauson-Khand reaction of chiral amides derived from 8-nonen-2-ynoic acid. Hydride-mediated reduction of the resulting cyclopentenone adducts followed by acid-catalysed dehydration leads to the formation of the corresponding cyclopentadienes in good overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02328-0
• 作为产物：
  描述：

  8-nonen-2-ynoic acid 在 sodium tetrahydroborate 、 N-羟基丁二酰亚胺 、 cerium(III) chloride 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 13.5h， 生成 (2-hydroxy-3,3a,4,5,6,7-hexahydro-2H-inden-1-yl)-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone
  参考文献：
  名称：

  An intramolecular Pauson–Khand approach to the synthesis of chiral cyclopentadienes

  摘要：

  A procedure for the synthesis of chirally-substituted cyclopentadienes has been developed by employing the intramolecular Pauson-Khand reaction of chiral amides derived from 8-nonen-2-ynoic acid. Hydride-mediated reduction of the resulting cyclopentenone adducts followed by acid-catalysed dehydration leads to the formation of the corresponding cyclopentadienes in good overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02328-0

文献信息

• An intramolecular Pauson–Khand approach to the synthesis of chiral cyclopentadienes
  作者：Ramon Rios、Albert Moyano、Miquel A Pericàs

  DOI：10.1016/s0040-4039(01)02328-0

  日期：2002.2

  A procedure for the synthesis of chirally-substituted cyclopentadienes has been developed by employing the intramolecular Pauson-Khand reaction of chiral amides derived from 8-nonen-2-ynoic acid. Hydride-mediated reduction of the resulting cyclopentenone adducts followed by acid-catalysed dehydration leads to the formation of the corresponding cyclopentadienes in good overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.