N,N-diallyl-5,5-diphenylpent-4-enylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-diallyl-5,5-diphenylpent-4-enylamine
• 英文别名: 5,5-diphenyl-N,N-bis(prop-2-enyl)pent-4-en-1-amine
• 化学式: C₂₃H₂₇N
• 分子量: 317.474
• InChiKey: LIKBJKVLQXYMLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diallyl-5,5-diphenylpent-4-enylamine 在 水 、 sodium carbonate 、 TBPA+PF6- 作用下， 以 乙腈 为溶剂， 以82%的产率得到1,1-diallyl-2-(1-hydroxydiphenylmethyl)pyrrolidinium hexafluorophosphate
  参考文献：
  名称：

  Triarylaminium Salt Induced Oxidative Cyclizations of Tertiary Amines. Convenient Access to 2-Substituted Pyrrolidinium Salts

  摘要：

  [GRAPHICS]Although they are common intermediates, the application of aliphatic tertiary aminium radical cations to organic synthesis has so far been restricted to a deprotonation and related reactions. We report the very convenient oxidative generation and facile 5-exo cyclization of tertiary amimium radical cations to distonic 2-substituted pyrrolidinium radical cations. These can be further oxidized to 1,3-dications and trapped by nucleophiles as water, alcohols, or chloride ion. Preliminary mechanistic issues and implications will be presented.

  DOI：

  10.1021/ol990735c
• 作为产物：
  描述：

  5,5-diphenyl-4-pentenyl bromide 、 二烯丙基胺 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以97%的产率得到N,N-diallyl-5,5-diphenylpent-4-enylamine
  参考文献：
  名称：

  Triarylaminium Salt Induced Oxidative Cyclizations of Tertiary Amines. Convenient Access to 2-Substituted Pyrrolidinium Salts

  摘要：

  [GRAPHICS]Although they are common intermediates, the application of aliphatic tertiary aminium radical cations to organic synthesis has so far been restricted to a deprotonation and related reactions. We report the very convenient oxidative generation and facile 5-exo cyclization of tertiary amimium radical cations to distonic 2-substituted pyrrolidinium radical cations. These can be further oxidized to 1,3-dications and trapped by nucleophiles as water, alcohols, or chloride ion. Preliminary mechanistic issues and implications will be presented.

  DOI：

  10.1021/ol990735c

文献信息

• Triarylaminium Salt Induced Oxidative Cyclizations of Tertiary Amines. Convenient Access to 2-Substituted Pyrrolidinium Salts
  作者：Ullrich Jahn、Susanne Aussieker

  DOI：10.1021/ol990735c

  日期：1999.9.1

  [GRAPHICS]Although they are common intermediates, the application of aliphatic tertiary aminium radical cations to organic synthesis has so far been restricted to a deprotonation and related reactions. We report the very convenient oxidative generation and facile 5-exo cyclization of tertiary amimium radical cations to distonic 2-substituted pyrrolidinium radical cations. These can be further oxidized to 1,3-dications and trapped by nucleophiles as water, alcohols, or chloride ion. Preliminary mechanistic issues and implications will be presented.