4-(1-adamantyl)-1,2,3-thiadiazole | 895325-89-0

• 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)-1,2,3-thiadiazole
• 英文别名: 4-(1-adamantyl)thiadiazole
• CAS: 895325-89-0
• 化学式: C₁₂H₁₆N₂S
• mdl: MFCD07180950
• 分子量: 220.338
• InChiKey: YWPMUERIBFGRJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1-adamantyl)-1,2,3-thiadiazole 在 甲醇 、 sodium 作用下， 反应 1.0h， 生成 O-methyl (1-adamantyl)thioacetate
  参考文献：
  名称：

  New method for the preparation of N,N-dimethyl-(thioacetamides) from 4-substituted 1,2,3-thiadiazoles

  摘要：

  DOI：

  10.1134/s1070428007120226
• 作为产物：
  描述：

  1-金刚烷甲酮 在 盐酸 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-(1-adamantyl)-1,2,3-thiadiazole
  参考文献：
  名称：

  4-(1-Adamantyl)-1,2,3-thiadiazole as a source of adamantylethynyl sulfides

  摘要：

  DOI：

  10.1134/s1070428007040276

文献信息

• Alkali metal 2-(1-adamantyl)ethynethiolates: Synthesis and reactions with electrophilic reagents
  作者：M. L. Petrov、A. A. Shchipalkin、V. A. Kuznetsov、B. N. Viktorov

  DOI：10.1134/s1070428010080166

  日期：2010.8

  Treatment of ethyl 2-[1-(1-admantyl)ethylidene]hydrazine-1-carboxylate with thionyl chloride gave 4-(1-adamantyl)-1,2,3-thiadiazole which readily underwent decomposition by the action of strong bases with formation of alkali metal 2-(1-adamantyl)ethynethiolates. The latter were brought into reactions with proton donors and benzyl halides.
• Reaction of potassium 2-(1-adamantyl)ethynethiolate with nitrilimines
  作者：M. L. Petrov、A. A. Shchipalkin、V. A. Kuznetsov

  DOI：10.1134/s1070428011110248

  日期：2011.11
• 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.
• New convenient method for preparation of amides of 1-adamantylthioacetic acids
  作者：A. A. Shchipalkin、M. L. Petrov、V. A. Kuznetsov

  DOI：10.1134/s107042801108015x

  日期：2011.8

  The reaction of 4-(1-adamantyl)-1,2,3-thiadiazole with potassium tert-butylate followed by treating with acetyl chloride and amine results in the formation of 1-adamantylthioacetic acid amides in moderate or good yields.
• New method of preparation of 1-adamantylthioacetic acids dialkylamides from 4-(1-adamantyl)-1,2,3-thiadiazole
  作者：M. L. Petrov、A. A. Shchipalkin、V. A. Kuznetsov

  DOI：10.1134/s1070428008050254

  日期：2008.5