2,4,5-trichlorophenyl N-methylcarbamate | 3942-57-2

• 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: 2,4,5-trichlorophenyl N-methylcarbamate
• 英文别名: methyl-carbamic acid-(2,4,5-trichloro-phenyl ester)；Methyl-carbamidsaeure-(2,4,5-trichlor-phenylester)；2,4,5-Trichlorophenyl methylcarbamate；(2,4,5-trichlorophenyl) N-methylcarbamate
• CAS: 3942-57-2
• 化学式: C₈H₆Cl₃NO₂
• 分子量: 254.5
• InChiKey: NFKDYWQXMAXPKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,5-trichlorophenyl N-methylcarbamate 在 吡啶 、 亚硝酰氯 作用下， 反应 2.0h， 以94%的产率得到N-methyl N-nitrosocarbamate de trichloro-2,4,5 phenyle
  参考文献：
  名称：

  Activated N-nitrosocarbamates for regioselective synthesis of N-nitrosoureas

  摘要：

  A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N-nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed. N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N-nitrosoureas. As an interesting example, N,N'-bis[(2-chloroethyl)nitrosocarbamoyl]cystamine, a new attractive oncostatic derivative, has been prepared. The cytotoxic activity of these various compounds were tested on L1210 leukemia.

  DOI：

  10.1021/jm00344a017
• 作为产物：
  描述：

  2,4,5-三氯苯酚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 59.0h， 生成 2,4,5-trichlorophenyl N-methylcarbamate
  参考文献：
  名称：

  A Convenient Method for the Synthesis of ActivatedN-Methylcarbamates

  摘要：

  报道了一种高效制备活性N-甲基氨基甲酸酯的方法。由相应氯甲酸酯5a-e制备了N-（甲基氨基甲酰氧基）琥珀酰亚胺（3a）、芳基N-甲基氨基甲酸酯3b-d和2,2,2-三氟-1-（三氟甲基）乙基N-甲基氨基甲酸酯（3e），产率为70-80%。这些氯甲酸酯是通过三氯甲基氯甲酸酯（1）或双（三氯甲基）碳酸酯（2）与羟基化合物4a-e的缩合反应，以高产率制备的结晶固体。

  DOI：

  10.1055/s-1993-25809

文献信息

• Insecticide Structure and Activity, Insecticidal Activity of Carbamate Cholinesterase Inhibitors
  作者：M. J. Kolbezen、R. L. Metcalf、T. R. Fukuto

  DOI：10.1021/jf60037a003

  日期：1954.8
• US3938986A
  申请人：——

  公开号：US3938986A

  公开（公告）日：1976-02-17
• Activated N-nitrosocarbamates for regioselective synthesis of N-nitrosoureas
  作者：Jean Martinez、Joel Oiry、Jean Louis Imbach、Francois Winternitz

  DOI：10.1021/jm00344a017

  日期：1982.2

  A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N-nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed. N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N-nitrosoureas. As an interesting example, N,N'-bis[(2-chloroethyl)nitrosocarbamoyl]cystamine, a new attractive oncostatic derivative, has been prepared. The cytotoxic activity of these various compounds were tested on L1210 leukemia.
• A Convenient Method for the Synthesis of Activated<i>N</i>-Methylcarbamates
  作者：Takeo Konakahara、Tomokazu Ozaki、Kenji Sato、Barry Gold

  DOI：10.1055/s-1993-25809

  日期：——

  An investigation of methods to efficiently prepare activated N-methylcarbamates is reported. N-(Methylcarbamoyloxy)succinimide (3a), aryl N-methylcarbamates 3b-d and 2,2,2-trifluoro-1-(trifluoromethyl)ethyl N-methylcarbamate (3e) have been prepared in 70-80% yields from the corresponding chloroformates 5a-e, which were prepared as crystalline solids by the condensation of trichloromethyl chloroformate (1) or bis(trichloromethyl) carbonate (2) with hydroxy compounds 4a-e in high yields.

  报道了一种高效制备活性N-甲基氨基甲酸酯的方法。由相应氯甲酸酯5a-e制备了N-（甲基氨基甲酰氧基）琥珀酰亚胺（3a）、芳基N-甲基氨基甲酸酯3b-d和2,2,2-三氟-1-（三氟甲基）乙基N-甲基氨基甲酸酯（3e），产率为70-80%。这些氯甲酸酯是通过三氯甲基氯甲酸酯（1）或双（三氯甲基）碳酸酯（2）与羟基化合物4a-e的缩合反应，以高产率制备的结晶固体。