N-(1-aza-1,3-heptadienyl)phthalimide | 651311-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(1-aza-1,3-heptadienyl)phthalimide
• 英文别名: 2-[(E)-[(E)-hex-2-enylidene]amino]isoindole-1,3-dione
• CAS: 651311-13-6
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: XVLSRNLWIBDJQF-ZMZMSIHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1-aza-1,3-heptadienyl)phthalimide 在 甲烷磺酸 、 四甲基乙二胺 、 copper(l) chloride 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 23.0h， 生成 (+/-)-(4R)-N-(phthalimido)-3,3-dichloro-4-[(1R)-(1-chlorobutyl)]-2-pyrrolidinone
  参考文献：
  名称：

  Hydro-de-halogenation and consecutive deprotection of chlorinated N-amido-pyrrolidin-2-ones with Raney-Ni: an effective approach to gabapentin

  摘要：

  The benzoylamino group was identified as a useful radical cyclization auxiliary that can be smoothly removed on hydro-dehalogenation of chlorinated N-substituted-pyrrolidin-2-ones with Raney-Ni. This methodology was successfully implemented in a new and appealing route to the anti-epileptic drug gabapentin. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2003.10.046
• 作为产物：
  描述：

  2-已烯醛 、 氨基邻苯二甲胺 以 二氯甲烷 为溶剂， 生成 N-(1-aza-1,3-heptadienyl)phthalimide
  参考文献：
  名称：

  Hydro-de-halogenation and consecutive deprotection of chlorinated N-amido-pyrrolidin-2-ones with Raney-Ni: an effective approach to gabapentin

  摘要：

  The benzoylamino group was identified as a useful radical cyclization auxiliary that can be smoothly removed on hydro-dehalogenation of chlorinated N-substituted-pyrrolidin-2-ones with Raney-Ni. This methodology was successfully implemented in a new and appealing route to the anti-epileptic drug gabapentin. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2003.10.046

文献信息

• Hydro-de-halogenation and consecutive deprotection of chlorinated N-amido-pyrrolidin-2-ones with Raney-Ni: an effective approach to gabapentin
  作者：Rita Cagnoli、Franco Ghelfi、Ugo M Pagnoni、Andrew F Parsons、Luisa Schenetti

  DOI：10.1016/j.tet.2003.10.046

  日期：2003.12

  The benzoylamino group was identified as a useful radical cyclization auxiliary that can be smoothly removed on hydro-dehalogenation of chlorinated N-substituted-pyrrolidin-2-ones with Raney-Ni. This methodology was successfully implemented in a new and appealing route to the anti-epileptic drug gabapentin. (C) 2003 Published by Elsevier Ltd.