5,5-Dimethyl-2-<(methoxycarbonyl-2-oxo)ethylidene>pyrrolidine | 140116-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5,5-Dimethyl-2-<(methoxycarbonyl-2-oxo)ethylidene>pyrrolidine
• 英文别名: 5,5-Dimethyl-2-[(methoxycarbonyl-2-oxo)ethylidene]pyrrolidine；methyl (2E)-2-(5,5-dimethylpyrrolidin-2-ylidene)-3-oxopropanoate
• CAS: 140116-98-9
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: ZZFUFDRYVBRSAK-BQYQJAHWSA-N

物化性质

• 沸点：
  315.8±42.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 、 丙炔酸甲酯 以 乙醚 为溶剂， 反应 12.0h， 以27%的产率得到5,5-Dimethyl-2-<(methoxycarbonyl-2-oxo)ethylidene>pyrrolidine
  参考文献：
  名称：

  Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes

  摘要：

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.

  DOI：

  10.1016/s0040-4020(01)88127-8

文献信息

• Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes
  作者：Hans Günter Aurich、Michael Franzke、Hans Peter Kesselheim、Markus Rohr

  DOI：10.1016/s0040-4020(01)88127-8

  日期：——

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.