2,2-diphenyl-5-ethoxycarbonyl-3,4-dihydro-2H-pyrrole

• 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: 2,2-diphenyl-5-ethoxycarbonyl-3,4-dihydro-2H-pyrrole
• 英文别名: Ethyl 5,5-diphenyl-3,4-dihydropyrrole-2-carboxylate
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: NXNDHGKGPSRFEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-氨基环丙烷羧酸乙酯 在 3 A molecular sieve 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 28.0h， 生成 2,2-diphenyl-5-ethoxycarbonyl-3,4-dihydro-2H-pyrrole
  参考文献：
  名称：

  The N-Cyclopropylimine-1-pyrroline Photorearrangement as a Synthetic Tool:  Scope and Limitations

  摘要：

  [GRAPHICS]The scope and limitations of the photorearrangement of N-cyclopropylimines to 1-pyrrolines are presented. The influence on the reactivity of different substituents throughout the cyclopropane ring and at the iminic position of the N-cyclopropylimine structure is discussed. The observed effects are interpreted from computational studies. The principal findings relate to (1) the enhanced reactivity of 1-substituted compounds toward rearrangement, (2) the lack of reactivity of crowded cyclopropanes, and (3) the high chemoselectivity of the process.

  DOI：

  10.1021/jo050871x

文献信息

• The <i>N</i>-Cyclopropylimine-1-pyrroline Photorearrangement as a Synthetic Tool:  Scope and Limitations
  作者：Alberto Soldevilla、Diego Sampedro、Pedro J. Campos、Miguel A. Rodríguez

  DOI：10.1021/jo050871x

  日期：2005.8.1

  [GRAPHICS]The scope and limitations of the photorearrangement of N-cyclopropylimines to 1-pyrrolines are presented. The influence on the reactivity of different substituents throughout the cyclopropane ring and at the iminic position of the N-cyclopropylimine structure is discussed. The observed effects are interpreted from computational studies. The principal findings relate to (1) the enhanced reactivity of 1-substituted compounds toward rearrangement, (2) the lack of reactivity of crowded cyclopropanes, and (3) the high chemoselectivity of the process.