Methyl 2-{[(2-chloroethyl)amino]carbonyl}hydrazinecarboxylate | 680860-16-6

• 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: Methyl 2-{[(2-chloroethyl)amino]carbonyl}hydrazinecarboxylate
• 英文别名: methyl N-(2-chloroethylcarbamoylamino)carbamate
• CAS: 680860-16-6
• 化学式: C₅H₁₀ClN₃O₃
• mdl: MFCD20542189
• 分子量: 195.606
• InChiKey: AMOAIVFLCYHJSD-UHFFFAOYSA-N

物化性质

• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-{[(2-chloroethyl)amino]carbonyl}hydrazinecarboxylate 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以74%的产率得到methyl (2-chloroethylamino)carbonyldiazenecarboxylate
  参考文献：
  名称：

  Electrophilic Amination of 4-Fluorophenol with Diazenes:  A Complete Removal of the Fluorine Atom

  摘要：

  The electrophilic amination of 2-fluorophenol, 4-fluorophenol, and 2-chlorophenol was observed to occur as a result of their treatment with diazenes 1-4 under mild reaction conditions in the presence of ZrCl4. The products originating from the 2-fluorophenol or 2-chlorophenol can be considered as "normal" products of amination. On the other hand, the 2-chloro-4-amino-substituted phenols obtained from the 4-fluorophenol seem to be formed in a process that involves an ipso amination, the complete removal of the fluorine atom, and the introduction of the chlorine atom.

  DOI：

  10.1021/jo035856b
• 作为产物：
  描述：

  氯乙基异氰酸酯 、 肼基甲酸甲酯 以 乙腈 为溶剂， 生成 Methyl 2-{[(2-chloroethyl)amino]carbonyl}hydrazinecarboxylate
  参考文献：
  名称：

  Diazenedicarboxamides as inhibitors of d-alanine-d-alanine ligase (Ddl)

  摘要：

  D-Alanine-D-alanine ligase (Ddl) catalyzes the biosynthesis of an essential bacterial peptidoglycan precursor D-alanyl-D-alanine and it represents an important target for development of new antibacterial drugs. A series of semicarbazides, aminocarbonyldiazenecarboxylates, diazenedicarboxamides, and hydrazinedicarboxamides was synthesized and screened for inhibition of DdlB from Escherichia coli. Compounds with good inhibitory activity were identified, enabling us to deduce initial structure-activity relationships. Thirteen diazenedicarboxamides were better inhibitors than D-cycloserine and some of them also possess antibacterial activity, which makes them a promising starting point for further development. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.015