4-(1-adamantyl)-2-(4-chlorophenyl)-1,3-thiazole | 883041-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1-adamantyl)-2-(4-chlorophenyl)-1,3-thiazole
• CAS: 883041-51-8
• 化学式: C₁₉H₂₀ClNS
• 分子量: 329.894
• InChiKey: WKCZMZGMFFFUOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(1-adamantyl)-1,2,3-thiadiazole 在 potassium tert-butylate 、 ammonium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 6.75h， 生成 4-(1-adamantyl)-2-(4-chlorophenyl)-1,3-thiazole
  参考文献：
  名称：

  New synthesis of 4-(1-adamantyl)-2-aryl-1,3-thiazoles from 4-(1-adamantyl)-1,2,3-thiadiazole

  摘要：

  Treatment of 4-(1-adamantyl)-1,2,3-thiadiazole with potassium tert-butoxide generated potassium 2-(1-adamantyl)ethynethiolate which reacted with aromatic carboxylic acid chlorides to give unstable S-[2-(1-adamantyl)ethynyl] arenecarbothioates whose acid hydrolysis afforded S-[ 2-(1-adamantyl)-2-oxoethyl] arenecarbothioates. The latter reacted with ammonium acetate in acetic acid yielding 4-(1-adamantyl)-2-aryl-1,3-thiadiazoles. Reactions of 4-(1-adamantyl)-2-(4-chloro-3-nitrophenyl)-1,3-thiadiazole with cyclic secondary amines gave the corresponding products of nucleophilic replacement of the chlorine atom in the aromatic ring.

  DOI：

  10.1134/s1070428011120165

文献信息

• New synthesis of 4-(1-adamantyl)-2-aryl-1,3-thiazoles from 4-(1-adamantyl)-1,2,3-thiadiazole
  作者：A. A. Shchipalkin、M. L. Petrov、V. A. Kuznetsov

  DOI：10.1134/s1070428011120165

  日期：2011.12

  Treatment of 4-(1-adamantyl)-1,2,3-thiadiazole with potassium tert-butoxide generated potassium 2-(1-adamantyl)ethynethiolate which reacted with aromatic carboxylic acid chlorides to give unstable S-[2-(1-adamantyl)ethynyl] arenecarbothioates whose acid hydrolysis afforded S-[ 2-(1-adamantyl)-2-oxoethyl] arenecarbothioates. The latter reacted with ammonium acetate in acetic acid yielding 4-(1-adamantyl)-2-aryl-1,3-thiadiazoles. Reactions of 4-(1-adamantyl)-2-(4-chloro-3-nitrophenyl)-1,3-thiadiazole with cyclic secondary amines gave the corresponding products of nucleophilic replacement of the chlorine atom in the aromatic ring.