ethyl cyano[5-(4-cyanobenzoyl)-2-phenylthiazol-4-yl]acetate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl cyano[5-(4-cyanobenzoyl)-2-phenylthiazol-4-yl]acetate
• 英文别名: Ethyl 2-cyano-2-[5-(4-cyanobenzoyl)-2-phenyl-1,3-thiazol-4-yl]acetate；ethyl 2-cyano-2-[5-(4-cyanobenzoyl)-2-phenyl-1,3-thiazol-4-yl]acetate
• 化学式: C₂₂H₁₅N₃O₃S
• 分子量: 401.445
• InChiKey: MNNIKONBFNXZEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-溴-4'-氰基苯乙酮 、 6-Imino-4-methylsulfanyl-2-phenyl-6H-[1,3]thiazine-5-carboxylic acid ethyl ester; compound with perchloric acid 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以70%的产率得到ethyl cyano[5-(4-cyanobenzoyl)-2-phenylthiazol-4-yl]acetate
  参考文献：
  名称：

  A New Synthesis of Thiazole Derivatives via Ring Transformation of 6-Imino-6H- 1,3-thiazine Hydroperchlorates

  摘要：

  2-Arylthiazoles (8) with a cyanoacetate moiety in position 4 were synthesized by a new ring transformation reaction. Therefore 2-aryl-6-imino-6H-1,3-thiazinecarboxylic ester hydroperchlorates (3) were converted into 2-arylthiazoles (8) by reaction with acceptor substituted halomethanes (e.g. chloroacetonitrile, chloroacetic acid ester or phenacyl bromide). Using 2-(2-hydroxyphenyl)-6H-1,3-thiazinecarboxylic-acid ester hydroperchlorate (3c) as the starting compound the benzoxazine (11a) was obtained. Starting from 2-(4-chlorophenyl)-6H-1,3-thiazinecarboxylic-acid ester hydroperchlorate (3b) the thiazolo[5,4-c]pyridine (9e) was the final product.

  DOI：

  10.3987/com-04-10174

文献信息

• A New Synthesis of Thiazole Derivatives via Ring Transformation of 6-Imino-6H- 1,3-thiazine Hydroperchlorates
  作者：Detlef Briel

  DOI：10.3987/com-04-10174

  日期：——

  2-Arylthiazoles (8) with a cyanoacetate moiety in position 4 were synthesized by a new ring transformation reaction. Therefore 2-aryl-6-imino-6H-1,3-thiazinecarboxylic ester hydroperchlorates (3) were converted into 2-arylthiazoles (8) by reaction with acceptor substituted halomethanes (e.g. chloroacetonitrile, chloroacetic acid ester or phenacyl bromide). Using 2-(2-hydroxyphenyl)-6H-1,3-thiazinecarboxylic-acid ester hydroperchlorate (3c) as the starting compound the benzoxazine (11a) was obtained. Starting from 2-(4-chlorophenyl)-6H-1,3-thiazinecarboxylic-acid ester hydroperchlorate (3b) the thiazolo[5,4-c]pyridine (9e) was the final product.