2-amino-3-(4-chlorophenyl)-3-methyl-5-(naphthalen-2-ylthio)-3H-pyrrole-4-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-3-(4-chlorophenyl)-3-methyl-5-(naphthalen-2-ylthio)-3H-pyrrole-4-carbonitrile
• 英文别名: 5-Amino-4-(4-chlorophenyl)-4-methyl-2-naphthalen-2-ylsulfanylpyrrole-3-carbonitrile；5-amino-4-(4-chlorophenyl)-4-methyl-2-naphthalen-2-ylsulfanylpyrrole-3-carbonitrile
• 化学式: C₂₂H₁₆ClN₃S
• 分子量: 389.908
• InChiKey: HZSXJFVKOOSDOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  62.17
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  对氯苯乙酮 、 2-萘硫醇 、 丙二腈 在 三乙胺 作用下， 以 水 为溶剂， 反应 3.0h， 以92%的产率得到2-amino-3-(4-chlorophenyl)-3-methyl-5-(naphthalen-2-ylthio)-3H-pyrrole-4-carbonitrile
  参考文献：
  名称：

  Exploitation of Dual Character of CN Moiety in the Synthesis of Uniquely Decorated 3H-Pyrroles: A Rare Observation

  摘要：

  This is the first report of an innovative, one-pot, organocatalyzed, multicomponent synthesis of 3H-pyrroles from ketones, thiols, and malononitrile in ecofriendly solvent water. The approach to 3H-pyrroles presented herein offers, for the first time, an unprecedented coupling which leads to the construction of the nitrogen containing ring without starting from any amine moiety. In this context, cyanide-based multicomponent reactions involving the dual nature of the CN moiety has blossomed in an unprecedented way.

  DOI：

  10.1021/ol402950a

文献信息

• Exploitation of Dual Character of CN Moiety in the Synthesis of Uniquely Decorated 3<i>H</i>-Pyrroles: A Rare Observation
  作者：Paramita Das、Suman Ray、Chhanda Mukhopadhyay

  DOI：10.1021/ol402950a

  日期：2013.11.15

  This is the first report of an innovative, one-pot, organocatalyzed, multicomponent synthesis of 3H-pyrroles from ketones, thiols, and malononitrile in ecofriendly solvent water. The approach to 3H-pyrroles presented herein offers, for the first time, an unprecedented coupling which leads to the construction of the nitrogen containing ring without starting from any amine moiety. In this context, cyanide-based multicomponent reactions involving the dual nature of the CN moiety has blossomed in an unprecedented way.