(2S)-2-[benzyl(prop-2-enyl)amino]-3-(1H-indol-3-yl)-N,N-dimethylpropanamide | 252954-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2S)-2-[benzyl(prop-2-enyl)amino]-3-(1H-indol-3-yl)-N,N-dimethylpropanamide
• CAS: 252954-41-9
• 化学式: C₂₃H₂₇N₃O
• 分子量: 361.487
• InChiKey: BGXFLILUSPGXKM-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-[benzyl(prop-2-enyl)amino]-3-(1H-indol-3-yl)-N,N-dimethylpropanamide 在 三异丙氧基氯化钛 、 Cyclopentylmagnesium chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 2.0h， 生成 (1R,2S,5S)-3-benzyl-2-(1H-indol-3-ylmethyl)-3-aza-bicyclo[3.1.0]hex-1-yl-dimethylamine 、 (1S,2S,5R)-3-benzyl-2-(1H-indol-3-ylmethyl)-3-aza-bicyclo[3.1.0]hex-1-yl-dimethylamine
  参考文献：
  名称：

  Synthesis of Bicyclic Cyclopropylamines by Intramolecular Cyclopropanation of N-Allylamino Acid Dimethylamides

  摘要：

  [GRAPHICS]Cyclopropylamines and substituted cyclopropylamines are important building blocks or substituents in a variety of biologically active compounds, Here, we report the facile syntheses of cyclopropylamines by Ti(ll) mediated intramolecular coupling of a terminal olefinic moiety and the N,N dimethylcarboxamide moiety of amino acid derivatives. The products have novel and strained bicyclic structures. The yields were good (78-83%) for all three substrates with diastereomeric ratios of about 3:1.

  DOI：

  10.1021/ol9910520
• 作为产物：
  描述：

  methyl N-benzyl-L-tryptophanate 在 三甲基铝 、 碳酸氢钠 作用下， 生成 (2S)-2-[benzyl(prop-2-enyl)amino]-3-(1H-indol-3-yl)-N,N-dimethylpropanamide
  参考文献：
  名称：

  Synthesis of Bicyclic Cyclopropylamines by Intramolecular Cyclopropanation of N-Allylamino Acid Dimethylamides

  摘要：

  [GRAPHICS]Cyclopropylamines and substituted cyclopropylamines are important building blocks or substituents in a variety of biologically active compounds, Here, we report the facile syntheses of cyclopropylamines by Ti(ll) mediated intramolecular coupling of a terminal olefinic moiety and the N,N dimethylcarboxamide moiety of amino acid derivatives. The products have novel and strained bicyclic structures. The yields were good (78-83%) for all three substrates with diastereomeric ratios of about 3:1.

  DOI：

  10.1021/ol9910520

文献信息

• Synthesis of Bicyclic Cyclopropylamines by Intramolecular Cyclopropanation of <i>N</i>-Allylamino Acid Dimethylamides
  作者：Bin Cao、Dong Xiao、Madeleine M. Joullié

  DOI：10.1021/ol9910520

  日期：1999.12.1

  [GRAPHICS]Cyclopropylamines and substituted cyclopropylamines are important building blocks or substituents in a variety of biologically active compounds, Here, we report the facile syntheses of cyclopropylamines by Ti(ll) mediated intramolecular coupling of a terminal olefinic moiety and the N,N dimethylcarboxamide moiety of amino acid derivatives. The products have novel and strained bicyclic structures. The yields were good (78-83%) for all three substrates with diastereomeric ratios of about 3:1.