(E)-N-(1-cyclopentylethyl)-N-(hex-3-en-1-yl)aniline

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-N-(1-cyclopentylethyl)-N-(hex-3-en-1-yl)aniline
• 英文别名: N-(1-cyclopentylethyl)-N-[(E)-hex-3-enyl]aniline
• 化学式: C₁₉H₂₉N
• 分子量: 271.446
• InChiKey: ADBGZYYMGXEFRP-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-((E)-hex-3-enyl)-N-phenylethanethioamide 、 Cyclopentylmagnesium chloride 在 titanium(IV) isopropylate 、 氨 作用下， 以 乙醚 、 甲基叔丁基醚 、 水 为溶剂， 反应 1.0h， 以32%的产率得到(E)-N-(hex-3-en-1-yl)aniline
  参考文献：
  名称：

  Ti-mediated intramolecular cyclopropanation of N-alkenyl thioamides: scope and mechanistic study

  摘要：

  Although thioamides generally undergo a reductive alkylation process when they are treated with a Grignard reagent in the presence of Ti(OiPr)(4), substrates fitted with a but-3-enyl substitution at the nitrogen atom are shown to be converted into bicyclic aminocyclopropanes. These reactions are compared with the similar cyclisations of the corresponding carboxylic amide substrates. A mechanistic study is provided. Coincidently, new reagent systems are identified for the mediation of the same transformation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.006

文献信息

• Studies on the intramolecular Kulinkovich–de Meijere reaction of disubstituted alkenes bearing carboxylic amide groups
  作者：Nouara Ouhamou、Yvan Six

  DOI：10.1039/b306719j

  日期：——

  1,2-Disubstituted olefins bearing an acetamide group were found to undergo intramolecular Kulinkovich–de Meijere cyclopropanation in moderate yield but almost complete diastereoselectivity.

  研究发现，含有乙酰胺基团的 1,2-二取代烯烃可发生分子内 Kulinkovichâde Meijere 环丙烷化反应，产率中等，但几乎具有完全的非对映选择性。
• Ti-mediated intramolecular cyclopropanation of N-alkenyl thioamides: scope and mechanistic study
  作者：Fabien Hermant、Emmanuel Nicolas、Yvan Six

  DOI：10.1016/j.tet.2014.04.006

  日期：2014.6

  Although thioamides generally undergo a reductive alkylation process when they are treated with a Grignard reagent in the presence of Ti(OiPr)(4), substrates fitted with a but-3-enyl substitution at the nitrogen atom are shown to be converted into bicyclic aminocyclopropanes. These reactions are compared with the similar cyclisations of the corresponding carboxylic amide substrates. A mechanistic study is provided. Coincidently, new reagent systems are identified for the mediation of the same transformation. (C) 2014 Elsevier Ltd. All rights reserved.