6-Chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid phenylamide | 155185-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-Chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid phenylamide
• 英文别名: 4-chloro-1,3-dimethyl-2,6-dioxo-N-phenylpyrimidine-5-carboxamide
• CAS: 155185-72-1
• 化学式: C₁₃H₁₂ClN₃O₃
• 分子量: 293.71
• InChiKey: LAGODTCJJFFSBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid phenylamide 在 sodium hydrogensulfide 作用下， 以 乙醇 为溶剂， 生成 6-Mercapto-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid phenylamide
  参考文献：
  名称：

  The synthesis of pyrimidineisothiazolones. The effect of temperature on the addition of aryl amines to functionalized pyrimidines.

  摘要：

  A new synthesis for the hither-to-unknown pyrimidine isothiazolones 1 and 2 is detailed. The low temperature selectivity of amine nucleophiles on 6-chloropyrimidine-5-acylbromides (12) for the acylbromide over the ring chloride provides a new procedure for the functionalization of 5-carboxypyrimidines.

  DOI：

  10.1016/s0040-4039(00)61393-x
• 作为产物：
  描述：

  苯胺 、 6-氯-5-甲酰基-1,3-二甲基尿嘧啶 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三乙胺 作用下， 生成 6-Chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid phenylamide 、 1,3-Dimethyl-2,4-dioxo-6-phenylamino-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid phenylamide
  参考文献：
  名称：

  The synthesis of pyrimidineisothiazolones. The effect of temperature on the addition of aryl amines to functionalized pyrimidines.

  摘要：

  A new synthesis for the hither-to-unknown pyrimidine isothiazolones 1 and 2 is detailed. The low temperature selectivity of amine nucleophiles on 6-chloropyrimidine-5-acylbromides (12) for the acylbromide over the ring chloride provides a new procedure for the functionalization of 5-carboxypyrimidines.

  DOI：

  10.1016/s0040-4039(00)61393-x

文献信息

• The synthesis of pyrimidineisothiazolones. The effect of temperature on the addition of aryl amines to functionalized pyrimidines.
  作者：Carl P. Decicco、David J. Nelson

  DOI：10.1016/s0040-4039(00)61393-x

  日期：1993.12

  A new synthesis for the hither-to-unknown pyrimidine isothiazolones 1 and 2 is detailed. The low temperature selectivity of amine nucleophiles on 6-chloropyrimidine-5-acylbromides (12) for the acylbromide over the ring chloride provides a new procedure for the functionalization of 5-carboxypyrimidines.