N,N-Diphenyl-1-naphthalenemethanamine | 135505-51-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-Diphenyl-1-naphthalenemethanamine
• 英文别名: N-(naphthalen-1-ylmethyl)-N-phenylaniline
• CAS: 135505-51-0
• 化学式: C₂₃H₁₉N
• 分子量: 309.411
• InChiKey: GQPLZSWTWMIHRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  494.2±24.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  (benzyloxy)benzene 、 [1]naphthylmethylen-aniline 在 sodium 、 N,N-二甲基甲酰胺 作用下， 反应 0.5h， 以74%的产率得到N,N-Diphenyl-1-naphthalenemethanamine
  参考文献：
  名称：

  Novel synthesis of N,N-diarylarylmethanamines from N-(arylmethylene)arenamines and (arylmethoxy)arenes

  摘要：

  Various N,N-diarylarylmethanamines were synthesized by the reaction of N-(arylmethylene)arenamines with (arylmethoxy)arenes in dimethylformamide solution in the presence of a strong base as a catalyst which is obtained in situ by reacting metallic sodium with this solvent. In general, the reaction may be depicted as the reduction of the imine and addition, on the original imino nitrogen atom, of the aryl group (of the aryloxy moiety) of the ether and presumably oxidation of the arylmethoxy group of the either to its corresponding aldehyde. Side reactions and a proposed reaction mechanism are discussed.

  DOI：

  10.1021/jo00020a032

文献信息

• Aromatic tertiary amines, enamines, deoxybenzoins and benzils
  申请人：——

  公开号：US05011998A1

  公开（公告）日：1991-04-30

  A novel synthesis of aromatic tertiary amines involves reacting an aromatic anil and an aromatic ether in a molar ratio of 1:1; adjusting the ratio to 2:1 produces novel enamines and by employing a two step process for enamine production, various unsymmetrically substituted enamines can be obtained which are readily hydrolyzed to corresponding deoxybenzoins which in turn are readily oxidized to benzils, the aromatic tertiary amines may be used to produce charge transport layers in xerography, while the benzils may be used to produce a variety of desired polymers.

  一种新颖的芳香族三级胺的合成方法涉及将芳香族苯胺和芳香族醚以1:1的摩尔比反应；将比例调整为2:1则产生新的烯胺，通过采用两步法制备烯胺，可以获得各种不对称取代的烯胺，这些烯胺容易水解成相应的脱氧苯并酮，进而容易氧化成苯并酮，这些芳香族三级胺可用于在静电复印中产生电荷传输层，而苯并酮可用于产生各种所需的聚合物。
• US5011998A
  申请人：——

  公开号：US5011998A

  公开（公告）日：1991-04-30
• US5117062A
  申请人：——

  公开号：US5117062A

  公开（公告）日：1992-05-26
• US5196606A
  申请人：——

  公开号：US5196606A

  公开（公告）日：1993-03-23
• Novel synthesis of N,N-diarylarylmethanamines from N-(arylmethylene)arenamines and (arylmethoxy)arenes
  作者：Martino Paventi、Allan S. Hay

  DOI：10.1021/jo00020a032

  日期：1991.9

  Various N,N-diarylarylmethanamines were synthesized by the reaction of N-(arylmethylene)arenamines with (arylmethoxy)arenes in dimethylformamide solution in the presence of a strong base as a catalyst which is obtained in situ by reacting metallic sodium with this solvent. In general, the reaction may be depicted as the reduction of the imine and addition, on the original imino nitrogen atom, of the aryl group (of the aryloxy moiety) of the ether and presumably oxidation of the arylmethoxy group of the either to its corresponding aldehyde. Side reactions and a proposed reaction mechanism are discussed.