3-(3',3',4'-trimethyl-2'-oxapent-4'-en-1'-yl)indolizine | 1293931-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 3-(3',3',4'-trimethyl-2'-oxapent-4'-en-1'-yl)indolizine
• 英文别名: 3-(2,3-Dimethylbut-3-en-2-yloxymethyl)indolizine
• CAS: 1293931-98-2
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: VDIJEASBNWAVDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  13.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (Z)-2-(4'-trimethylsilyl-but-1'-en-3'-ynyl)pyridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.25h， 生成 3-(3',3',4'-trimethyl-2'-oxapent-4'-en-1'-yl)indolizine
  参考文献：
  名称：

  Experimental and Computational Exploration of Indolizinyl Carbene Generation. A Route to Biindolizines

  摘要：

  In previous work, (E)-2-enynyl. pyridines were reported to yield indolizinyl singlet carbenes through base-catalyzed E/Z isomerization followed by a 5-exo-dig pseudocoarctate cyclization. We report herein that in the presence of ethyl acrylate these carbenes undergo stereoselective cis-cyclopropanation due mainly to electrostatic interactions in the transition state. The scope of this carbene generation scheme has been further explored through the preparation of a symmetric bis(pyridylenyl)alkyne which spontaneously furnished the biindolizine core in a one-pot reaction. Computational characterization of this transformation suggests a highly asynchronous double cydization.

  DOI：

  10.1021/jo200157q

文献信息

• Experimental and Computational Exploration of Indolizinyl Carbene Generation. A Route to Biindolizines
  作者：Inmaculada R. Lahoz、Carlos Silva López、Armando Navarro-Vázquez、María-Magdalena Cid

  DOI：10.1021/jo200157q

  日期：2011.5.6

  In previous work, (E)-2-enynyl. pyridines were reported to yield indolizinyl singlet carbenes through base-catalyzed E/Z isomerization followed by a 5-exo-dig pseudocoarctate cyclization. We report herein that in the presence of ethyl acrylate these carbenes undergo stereoselective cis-cyclopropanation due mainly to electrostatic interactions in the transition state. The scope of this carbene generation scheme has been further explored through the preparation of a symmetric bis(pyridylenyl)alkyne which spontaneously furnished the biindolizine core in a one-pot reaction. Computational characterization of this transformation suggests a highly asynchronous double cydization.