5-(4-chlorophenyl)-2-cyclohexyl-3-(3-nitrophenyl)-1H-pyrrole | 1192372-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(4-chlorophenyl)-2-cyclohexyl-3-(3-nitrophenyl)-1H-pyrrole
• CAS: 1192372-37-4
• 化学式: C₂₂H₂₁ClN₂O₂
• 分子量: 380.874
• InChiKey: IGSNVVXNYNVADA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(对氯苯基)-3-(间硝基苯基)-2-丙烯-1-酮 、 2-amino-2-cyclohexylacetonitrile 在 四氯化钛 、 三乙胺 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.55h， 以34%的产率得到5-(4-chlorophenyl)-2-cyclohexyl-3-(3-nitrophenyl)-1H-pyrrole
  参考文献：
  名称：

  Cyclocondensation of α-Aminonitriles and Enones: A Short Access to 3,4-Dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-Trisubstituted Pyrroles

  摘要：

  The reaction of alpha,beta-unsaturated carbonyl compounds with aminoacetonitrile hydrochloride furnishes 3,5-disubstituted 3,4-dihydro-2H-pyrrole-2-carbonitriles in a one-pot reaction sequence. While these products can serve as starting materials for the preparation of polysubstituted pyrrolizidines, they are kinetically stable against the base-induced elimination of HCN. In contrast, their 2-substituted analogues obtained from alpha-substituted alpha-aminonitriles can be readily converted to the corresponding 2,3,5-trisubstituted pyrroles under microwave irradiation. The key step presumably involves the thermal electrocyclization of it stabilized 2-azapentadienyl anion Formed by condensation of the reactants and subsequent deprotonation.

  DOI：

  10.1021/jo901759u

文献信息

• Cyclocondensation of α-Aminonitriles and Enones: A Short Access to 3,4-Dihydro-2<i>H</i>-pyrrole 2-carbonitriles and 2,3,5-Trisubstituted Pyrroles
  作者：Ines Bergner、Christine Wiebe、Nino Meyer、Till Opatz

  DOI：10.1021/jo901759u

  日期：2009.11.6

  The reaction of alpha,beta-unsaturated carbonyl compounds with aminoacetonitrile hydrochloride furnishes 3,5-disubstituted 3,4-dihydro-2H-pyrrole-2-carbonitriles in a one-pot reaction sequence. While these products can serve as starting materials for the preparation of polysubstituted pyrrolizidines, they are kinetically stable against the base-induced elimination of HCN. In contrast, their 2-substituted analogues obtained from alpha-substituted alpha-aminonitriles can be readily converted to the corresponding 2,3,5-trisubstituted pyrroles under microwave irradiation. The key step presumably involves the thermal electrocyclization of it stabilized 2-azapentadienyl anion Formed by condensation of the reactants and subsequent deprotonation.