N-(4-chlorophenyl)-N'-methyl-N'-propargylurea | 69921-31-9

• 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: N-(4-chlorophenyl)-N'-methyl-N'-propargylurea
• 英文别名: 3-(4-Chlorophenyl)-1-methyl-1-prop-2-ynylurea
• CAS: 69921-31-9
• 化学式: C₁₁H₁₁ClN₂O
• 分子量: 222.674
• InChiKey: ZJDAOAVSXGDIOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-N'-methyl-N'-propargylurea 在 N-氯代丁二酰亚胺 、 copper dichloride 作用下， 以 乙腈 为溶剂， 以12%的产率得到(E)-5-(chloromethylidene)-2-[(4-chlorophenyl)imino]-3-methyloxazolidine
  参考文献：
  名称：

  Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles

  摘要：

  A highly effective synthesis of haloalkylidene-substituted heterocycles by copper(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl, and CuBr2, respectively.

  DOI：

  10.1021/acs.joc.5b01227
• 作为产物：
  描述：

  N-甲基炔丙基胺 、 对氯苯异氰酸酯 以 四氢呋喃 为溶剂， 以98%的产率得到N-(4-chlorophenyl)-N'-methyl-N'-propargylurea
  参考文献：
  名称：

  Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles

  摘要：

  A highly effective synthesis of haloalkylidene-substituted heterocycles by copper(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl, and CuBr2, respectively.

  DOI：

  10.1021/acs.joc.5b01227