3-(3-chloro-4-cyanophenyl)-2-thioxotetrahydropyrimidin-4(1H)-one | 1417455-80-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(3-chloro-4-cyanophenyl)-2-thioxotetrahydropyrimidin-4(1H)-one
• 英文别名: 2-Chloro-4-(6-oxo-2-sulfanylidene-1,3-diazinan-1-yl)benzonitrile；2-chloro-4-(6-oxo-2-sulfanylidene-1,3-diazinan-1-yl)benzonitrile
• CAS: 1417455-80-1
• 化学式: C₁₁H₈ClN₃OS
• 分子量: 265.723
• InChiKey: WHUNQABIPREYMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-4-异硫氰酰基苯氰 在 N,N'-羰基二咪唑 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.05h， 生成 3-(3-chloro-4-cyanophenyl)-2-thioxotetrahydropyrimidin-4(1H)-one
  参考文献：
  名称：

  A Facile Synthesis and Chemoselective Reactions of Dihydrothiouracils

  摘要：

  A highly efficient procedure was devised for the synthesis of 3-(3-arylthioureido)propanoic/butanoic acid and its cyclization to (3-aryl/3-aryl-6-methyl)-2-thioxotetrahydropyrimidin-4(1H)-one derivatives. Carbonyl diimidazole proved to be a very effective coupling reagent for the cyclization. Studies carried out to examine the ambident nature of the thioamide moiety towards substitution reactions demonstrated the preference for alkylation at sulfur, and acylation and 1,4-addition at nitrogen.

  DOI：

  10.1055/s-0032-1317133

文献信息

• A Facile Synthesis and Chemoselective Reactions of Dihydrothiouracils
  作者：Vipin Nair、Varun Kumar、Gopal Khatik、Anang Pal、Mohan Praneeth、Sanjay Bhattarai

  DOI：10.1055/s-0032-1317133

  日期：——

  A highly efficient procedure was devised for the synthesis of 3-(3-arylthioureido)propanoic/butanoic acid and its cyclization to (3-aryl/3-aryl-6-methyl)-2-thioxotetrahydropyrimidin-4(1H)-one derivatives. Carbonyl diimidazole proved to be a very effective coupling reagent for the cyclization. Studies carried out to examine the ambident nature of the thioamide moiety towards substitution reactions demonstrated the preference for alkylation at sulfur, and acylation and 1,4-addition at nitrogen.