2-Acetyl-1-benzyl-7-chloro-5-(methylthio)imidazo<1,2-c>-pyrimidin-3-one | 155670-24-9

• 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-Acetyl-1-benzyl-7-chloro-5-(methylthio)imidazo<1,2-c>-pyrimidin-3-one
• 英文别名: (1Z)-1-(1-benzyl-7-chloro-5-methylsulfanyl-3-oxoimidazo[1,2-c]pyrimidin-4-ium-2-ylidene)ethanolate
• CAS: 155670-24-9
• 化学式: C₁₆H₁₄ClN₃O₂S
• 分子量: 347.825
• InChiKey: PIJHOLLRUVRRMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Acetyl-1-benzyl-7-chloro-5-(methylthio)imidazo<1,2-c>-pyrimidin-3-one 在 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.17h， 以94.4%的产率得到2-Acetyl-5-amino-1-benzyl-7-chloroimidazo<1,2-c>pyrimidin-3-one
  参考文献：
  名称：

  Cyclodehydration of 5-[(Carboxymethyl)amino]pyrimidines. Synthesis and Characterization of Novel Mesoionic Imidazo[1,2-c]pyrimidin-3-ones

  摘要：

  The cyclodehydration of 5-(carboxymethyl)amino-substituted pyrimidines using acid anhydrides has provided a general synthesis of novel mesoionic imidazo [1,2-c] pyrimidin-3-one compounds. The complete structural characterization and chemical reactivity studies of these compounds, including X-ray crystal structures for compounds 9c and 16a, were determined. Compounds lacking a blocking group at N-1 were found to undergo clean alkylation at this position, under basic reaction conditions, with substituted alkyl chlorides. Imidazo[1,2-c] pyrimidin-3-ones having a benzyl group at N-1 were found to undergo substitution reactions on the pyrimidine ring in the presence of basic nucleophiles. Thus, replacement of a 5-methylthio over a 7-chloro substituent was favored, whereas the 7-chloro group was substituted in compounds where a 6-amino substituent was present. Exposure of imidazo[1,2-c]pyrimidin-3-ones to aqueous acid results in the ring opening of the five-membered ring with subsequent loss of carbon dioxide or trifluoroacetate in an overall net reversion of the cyclodehydration reaction. Examination of the X-ray structures obtained for compounds 9c and 16a indicated that the five-membered ring was not aromatic, but rather a combination of a ring-opened valence tautomer and a charge-delocalized resonance hybrid structure.

  DOI：

  10.1021/jo00088a031
• 作为产物：
  描述：

  4,6-二氯-二甲硫基嘧啶 在 碳酸氢钠 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.92h， 生成 2-Acetyl-1-benzyl-7-chloro-5-(methylthio)imidazo<1,2-c>-pyrimidin-3-one
  参考文献：
  名称：

  Cyclodehydration of 5-[(Carboxymethyl)amino]pyrimidines. Synthesis and Characterization of Novel Mesoionic Imidazo[1,2-c]pyrimidin-3-ones

  摘要：

  The cyclodehydration of 5-(carboxymethyl)amino-substituted pyrimidines using acid anhydrides has provided a general synthesis of novel mesoionic imidazo [1,2-c] pyrimidin-3-one compounds. The complete structural characterization and chemical reactivity studies of these compounds, including X-ray crystal structures for compounds 9c and 16a, were determined. Compounds lacking a blocking group at N-1 were found to undergo clean alkylation at this position, under basic reaction conditions, with substituted alkyl chlorides. Imidazo[1,2-c] pyrimidin-3-ones having a benzyl group at N-1 were found to undergo substitution reactions on the pyrimidine ring in the presence of basic nucleophiles. Thus, replacement of a 5-methylthio over a 7-chloro substituent was favored, whereas the 7-chloro group was substituted in compounds where a 6-amino substituent was present. Exposure of imidazo[1,2-c]pyrimidin-3-ones to aqueous acid results in the ring opening of the five-membered ring with subsequent loss of carbon dioxide or trifluoroacetate in an overall net reversion of the cyclodehydration reaction. Examination of the X-ray structures obtained for compounds 9c and 16a indicated that the five-membered ring was not aromatic, but rather a combination of a ring-opened valence tautomer and a charge-delocalized resonance hybrid structure.

  DOI：

  10.1021/jo00088a031