Non-8-en-2-ynoic acid ((S)-1-phenyl-ethyl)-amide | 439807-49-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Non-8-en-2-ynoic acid ((S)-1-phenyl-ethyl)-amide
• 英文别名: N-[(1S)-1-phenylethyl]non-8-en-2-ynamide
• CAS: 439807-49-5
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: JWLXJXMYMXCXJT-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Non-8-en-2-ynoic acid ((S)-1-phenyl-ethyl)-amide 、 alkaline earth salt of/the/ methylsulfuric acid 在 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 14.5h， 生成 2-Hydroxy-3,3a,4,5,6,7-hexahydro-2H-indene-1-carboxylic acid ((S)-1-phenyl-ethyl)-amide
  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：

  (S)-(-)- α-甲基苄胺 、 8-nonen-2-ynoic acid 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 以79%的产率得到Non-8-en-2-ynoic acid ((S)-1-phenyl-ethyl)-amide
  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.