2-(2,6-Dichloro-benzyl)-thiazole-4-carboxylic acid ethyl ester | 263015-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,6-Dichloro-benzyl)-thiazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-[(2,6-dichlorophenyl)methyl]-1,3-thiazole-4-carboxylate
• CAS: 263015-68-5
• 化学式: C₁₃H₁₁Cl₂NO₂S
• 分子量: 316.208
• InChiKey: YUOXEPMWIAGKQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,6-Dichloro-benzyl)-thiazole-4-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到2-(2,6-二氯苄基)-1,3-噻唑-4-羧酸
  参考文献：
  名称：

  A catch-and-release strategy for the combinatorial synthesis of 4-acylamino-1,3-thiazoles as potential CDK5 inhibitors

  摘要：

  Two-dimensional libraries of 4-acylamino-1,3-thiazoles 9 were prepared via Curtius rearrangement of 1,3-thiazole-4-carbonyl azides 6, trapping of the intermediate isocyanates with oxime resin, and thermal regeneration of the isocyanates from the washed resin in the presence of nucleophiles. Several compounds proved to be selective inhibitors of CDK5/p25 versus the closely homologous CDK2/cyclin A enzyme, with the best analogue (43) possessing over 100-fold selectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00726-1
• 作为产物：
  描述：

  3-溴丙酮酸乙酯 、 2-(2,6-二氯苯基)硫代乙酰胺 以30%的产率得到2-(2,6-Dichloro-benzyl)-thiazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  A catch-and-release strategy for the combinatorial synthesis of 4-acylamino-1,3-thiazoles as potential CDK5 inhibitors

  摘要：

  Two-dimensional libraries of 4-acylamino-1,3-thiazoles 9 were prepared via Curtius rearrangement of 1,3-thiazole-4-carbonyl azides 6, trapping of the intermediate isocyanates with oxime resin, and thermal regeneration of the isocyanates from the washed resin in the presence of nucleophiles. Several compounds proved to be selective inhibitors of CDK5/p25 versus the closely homologous CDK2/cyclin A enzyme, with the best analogue (43) possessing over 100-fold selectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00726-1