4-chloro-N-(chloromethyl)-N-methylbenzamide | 144175-29-1

• 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: 4-chloro-N-(chloromethyl)-N-methylbenzamide
• CAS: 144175-29-1
• 化学式: C₉H₉Cl₂NO
• 分子量: 218.083
• InChiKey: MCFQXIFYSNDOQU-UHFFFAOYSA-N

物化性质

• 沸点：
  340.0±27.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二苯基乙氧基膦 、 4-chloro-N-(chloromethyl)-N-methylbenzamide 以 甲苯 为溶剂， 反应 0.5h， 生成 N-(diphenyloxophosphinyl)methyl-N-methyl-4-chlorobenzamide
  参考文献：
  名称：

  Synthesis and Reactivity of Aliphatic and (Hetero) Aromatic N-Alkyl-N-(Diphenyloxophosphinyl) Methyl Carboxamides and Lactams

  摘要：

  A variety of aliphatic, aromatic and heteroaromatic N-alkyl-N-(diphenyloxophosphinyl)methyl carboxamides and lactams have been prepared by preliminar chloromethylation of the appropriate secondary amides and subsequent treatment with ethyl diphenylphosphinite.

  DOI：

  10.1080/00397919208019095
• 作为产物：
  描述：

  聚合甲醛 、 4-氯-N-甲基苯甲酰胺 在 三甲基氯硅烷 作用下， 反应 2.0h， 以100%的产率得到4-chloro-N-(chloromethyl)-N-methylbenzamide
  参考文献：
  名称：

  A new direct synthesis of tertiary N-acyloxymethylamide prodrugs of carboxylic acid drugs

  摘要：

  N-Alkyl-N-chloromethylamides 2, prepared from secondary amides, paraformaldehyde and chlorotrimethylsilane, react readily with carboxylate anions to generate the corresponding tertiary N-acyloxymethylamides 3 in good yield; the latter give rise to the parent carboxylic acids in aqueous media at pH 7.4 and 37 degrees C with half-lives between ca. 1 min and 42 h.

  DOI：

  10.1016/0040-4039(94)88238-x

文献信息

• Moreira Rui, Mendes Eduarda, Calheiros Teresa, Bacelo Maria J., Iley Jim, Tetrahedron Lett, 35 (1994) N 38, S 7107-7110
  作者：Moreira Rui, Mendes Eduarda, Calheiros Teresa, Bacelo Maria J., Iley Jim

  DOI：——

  日期：——
• A new direct synthesis of tertiary N-acyloxymethylamide prodrugs of carboxylic acid drugs
  作者：Rui Moreira、Eduarda Mendes、Teresa Calheiros、Maria J. Bacelo、Jim Iley

  DOI：10.1016/0040-4039(94)88238-x

  日期：1994.9

  N-Alkyl-N-chloromethylamides 2, prepared from secondary amides, paraformaldehyde and chlorotrimethylsilane, react readily with carboxylate anions to generate the corresponding tertiary N-acyloxymethylamides 3 in good yield; the latter give rise to the parent carboxylic acids in aqueous media at pH 7.4 and 37 degrees C with half-lives between ca. 1 min and 42 h.
• Synthesis and Reactivity of Aliphatic and (Hetero) Aromatic N-Alkyl-N-(Diphenyloxophosphinyl) Methyl Carboxamides and Lactams
  作者：Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1080/00397919208019095

  日期：1992.8

  A variety of aliphatic, aromatic and heteroaromatic N-alkyl-N-(diphenyloxophosphinyl)methyl carboxamides and lactams have been prepared by preliminar chloromethylation of the appropriate secondary amides and subsequent treatment with ethyl diphenylphosphinite.