alpha-(Chloroacetyl)-4-(4-chlorophenyl)-2-thiazoleacetonitrile | 428512-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: alpha-(Chloroacetyl)-4-(4-chlorophenyl)-2-thiazoleacetonitrile
• 英文别名: 4-chloro-2-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-3-oxobutanenitrile
• CAS: 428512-63-4
• 化学式: C₁₃H₈Cl₂N₂OS
• 分子量: 311.191
• InChiKey: ALRPORUQKILROG-UHFFFAOYSA-N

物化性质

• 沸点：
  442.2±45.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  alpha-(Chloroacetyl)-4-(4-chlorophenyl)-2-thiazoleacetonitrile 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-{5-Amino-4-[4-(4-chloro-phenyl)-thiazol-2-yl]-3-oxo-2,3-dihydro-pyrrol-1-yl}-benzoic acid (4-dimethylamino-phenylcarbamoyl)-methyl ester
  参考文献：
  名称：

  Chemoselective Alkylation of 3- and 4-(5-Amino-4-hetaryl-2,3-dihydro-3-oxopyrrol-1-yl)benzoic Acids

  摘要：

  Alkylation of 3- and 4-(5-amino-4-hetaryl-2,3-dihydro-3-oxopyrrol-1-yl)benzoic acids with phenacyl bromides or chloroacetanilides in DMF in the presence of triethylamine occurs at the carboxy group with high selectivity and yields the corresponding phenacyl and arylcarbamoylmethyl esters. The initial pyrrolyl-benzoic acids were synthesized by reaction of 3- and 4-aminobenzoic acids with 4-chloro-2-hetaryl-3-oxo-butyronitriles.

  DOI：

  10.1023/b:rujo.0000034973.29561.7c
• 作为产物：
  描述：

  氯乙酰氯 、 2-[4-(4-氟苯基)-1,3-噻唑-2-基]乙腈 在 吡啶 作用下， 生成 alpha-(Chloroacetyl)-4-(4-chlorophenyl)-2-thiazoleacetonitrile
  参考文献：
  名称：

  摘要：

  Reactions of 2-(4-aryl-1,3-thiazol-2-yl)-3-oxo-4-chlorobutyronitriles with primary aromatic amines result in nucleophilic substitution of the chlorine atom by amino group, followed by intramolecular addition of the secondary amino group to the cyano group. The products are 5-amino-1-aryl-4-(4-aryl-1,3-thiazol-2-yl)2,3-dihydro-1H-pyrrol-3-ones which are structurally related to the known antiischemic drugs.

  DOI：

  10.1023/a:1013196008180

文献信息

• ——
  作者：Yu. M. Volovenko、T. A. Volovnenko、A. V. Tverdokhlebov、I. G. Ryabokon'

  DOI：10.1023/a:1013196008180

  日期：——

  Reactions of 2-(4-aryl-1,3-thiazol-2-yl)-3-oxo-4-chlorobutyronitriles with primary aromatic amines result in nucleophilic substitution of the chlorine atom by amino group, followed by intramolecular addition of the secondary amino group to the cyano group. The products are 5-amino-1-aryl-4-(4-aryl-1,3-thiazol-2-yl)2,3-dihydro-1H-pyrrol-3-ones which are structurally related to the known antiischemic drugs.
• Chemoselective Alkylation of 3- and 4-(5-Amino-4-hetaryl-2,3-dihydro-3-oxopyrrol-1-yl)benzoic Acids
  作者：E. V. Resnyanskaya、A. V. Tverdokhlebov、Yu. M. Volovenko、T. V. Shokol

  DOI：10.1023/b:rujo.0000034973.29561.7c

  日期：2004.3

  Alkylation of 3- and 4-(5-amino-4-hetaryl-2,3-dihydro-3-oxopyrrol-1-yl)benzoic acids with phenacyl bromides or chloroacetanilides in DMF in the presence of triethylamine occurs at the carboxy group with high selectivity and yields the corresponding phenacyl and arylcarbamoylmethyl esters. The initial pyrrolyl-benzoic acids were synthesized by reaction of 3- and 4-aminobenzoic acids with 4-chloro-2-hetaryl-3-oxo-butyronitriles.