N,N-bis(3-chlorobenzyl)methylamine

• 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,N-bis(3-chlorobenzyl)methylamine
• 英文别名: bis-(3-chloro-benzyl)-methyl-amine；Bis-(3-chlor-benzyl)-methyl-amin；1-(3-chlorophenyl)-N-[(3-chlorophenyl)methyl]-N-methylmethanamine
• 化学式: C₁₅H₁₅Cl₂N
• 分子量: 280.197
• InChiKey: AXTDLSCKJFTPJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基-3-氰基苄胺 在 盐酸 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 N,N-bis(3-chlorobenzyl)methylamine 、 N-[(3-氰基苯基)甲基]-N-甲基亚硝酰胺
  参考文献：
  名称：

  Quantitative structure-activity relationship of the mutagenicity of substituted N-nitroso-N-benzylmethylamines: possible implications for carcinogenicity

  摘要：

  The relative mutagenicities of substituted N-nitroso-N-benzylmethylamines have been reexamined from a quantitative structure-activity relationship point of view. Most of the compounds were mutagenic toward Salmonella typhimurium TA 1535 with Aroclor-induced male hamster liver S9 activation. The dose-response data were subjected to a multiple linear regression equation calculated in a stepwise manner, which found that the differences in mutagenicities could be explained primarily by differences in the three-bond path molecular connectivity index, with smaller contributions from sigma and pi. Moreover, a polynomial regression analysis showed that the maximum mutagenicity could be explained by an optimal amount of electron withdrawal by the substituent which would cause a weakening, or activation, of the methylene C-H bond. The possible relevance of these observations to carcinogenesis is discussed.

  DOI：

  10.1021/jm00151a006

文献信息

• Reductive Aminomethylation Using Ammonium Formate and Methanol as N1 and C1 Source: Direct Synthesis of Mono- and Di-Methylated Amines
  作者：Ishani Borthakur、Srabani Nandi、Yuvraj Bilora、Biswajit Sadhu、Sabuj Kundu

  DOI：10.1021/acscatal.4c00346

  日期：2024.4.19

  single and dual reductive amination followed by N-methylation of aldehydes and ketones to synthesize N,N-dimethyl as well as N-methyl tertiary amines, respectively, utilizing ammonium formate and methanol as N1 and C1 sources is reported. The protocol was efficiently extended to a tandem reductive amination/N-methylation/cyclization of keto acids/esters leading to N-methyl lactams. A broad substrate

  Ir(III)配合物催化单还原胺化和双还原胺化，然后利用甲酸铵和甲醇作为N1和C1源，对醛和酮进行N-甲基化，分别合成N、N-二甲基和N-甲基叔胺：报道称。该方案被有效地扩展到酮酸/酯的串联还原胺化/ N-甲基化/环化，产生N-甲基内酰胺。还展示了广泛的底物范围、生物活性分子的合成。进行了控制实验、动力学研究和 DFT 计算，并在此基础上提出了合理的机制。
• v.Braun; Michaelis, Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
  作者：v.Braun、Michaelis

  DOI：——

  日期：——
• Quantitative structure-activity relationship of the mutagenicity of substituted N-nitroso-N-benzylmethylamines: possible implications for carcinogenicity
  作者：George M. Singer、A. W. Andrews、Shu Mei Guo

  DOI：10.1021/jm00151a006

  日期：1986.1

  The relative mutagenicities of substituted N-nitroso-N-benzylmethylamines have been reexamined from a quantitative structure-activity relationship point of view. Most of the compounds were mutagenic toward Salmonella typhimurium TA 1535 with Aroclor-induced male hamster liver S9 activation. The dose-response data were subjected to a multiple linear regression equation calculated in a stepwise manner, which found that the differences in mutagenicities could be explained primarily by differences in the three-bond path molecular connectivity index, with smaller contributions from sigma and pi. Moreover, a polynomial regression analysis showed that the maximum mutagenicity could be explained by an optimal amount of electron withdrawal by the substituent which would cause a weakening, or activation, of the methylene C-H bond. The possible relevance of these observations to carcinogenesis is discussed.