N-Ethyl(2-methyl-1-naphthyl)amine | 60632-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-Ethyl(2-methyl-1-naphthyl)amine
• 英文别名: 2-methyl-N-ethyl-α-naphthylamine；ethyl-(2-methyl-[1]naphthyl)-amine；Aethyl-(2-methyl-[1]naphthyl)-amin；1-Aethylamino-2-methyl-naphthalin；2-methyl-N-ethyl-alpha-naphthylamine；N-ethyl-2-methylnaphthalen-1-amine
• CAS: 60632-35-1
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: PUIGMKSCFCFVHK-UHFFFAOYSA-N

物化性质

• 沸点：
  108-109 °C(Press: 0.3 Torr)
• 密度：
  1.032 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Ethyl(2-methyl-1-naphthyl)amine 、 碘甲烷 在 甲基锂 作用下， 生成 N-Ethyl-N-methyl(2-methyl-1-naphthyl)amine
  参考文献：
  名称：

  Conformational studies by dynamic NMR. 40. Conformational atropoisomerism in highly hindered naphthylamines

  摘要：

  N,N-Dialkyl-1-naphthylamines substituted by alkyl groups R (R = Me, Et, i-Pr, t-Bu) in position 2 display anisochronous NMR signals owing to their twisted conformational arrangement. These conformers are enantiomerically related (conformational atropoisomers), and variable temperature NMR measurements allowed the enantiomerization barriers to be determined. The barriers increase with the increasing dimension of the substituents (covering the range 15.7-23.0 kcal mol-1), and the observed trend was reproduced by Molecular Mechanics calculations. The calculations also gave indications upon the structure of the conformers that correspond to energy minima. The final choice among the possible conformations could be achieved by comparing the computed interprotonic distances with the results of NOE experiments.

  DOI：

  10.1021/jo00005a017
• 作为产物：
  描述：

  2-甲基-二硝基萘酚 在 钯 甲基锂 、 氢气 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 N-Ethyl(2-methyl-1-naphthyl)amine
  参考文献：
  名称：

  Conformational studies by dynamic NMR. 40. Conformational atropoisomerism in highly hindered naphthylamines

  摘要：

  N,N-Dialkyl-1-naphthylamines substituted by alkyl groups R (R = Me, Et, i-Pr, t-Bu) in position 2 display anisochronous NMR signals owing to their twisted conformational arrangement. These conformers are enantiomerically related (conformational atropoisomers), and variable temperature NMR measurements allowed the enantiomerization barriers to be determined. The barriers increase with the increasing dimension of the substituents (covering the range 15.7-23.0 kcal mol-1), and the observed trend was reproduced by Molecular Mechanics calculations. The calculations also gave indications upon the structure of the conformers that correspond to energy minima. The final choice among the possible conformations could be achieved by comparing the computed interprotonic distances with the results of NOE experiments.

  DOI：

  10.1021/jo00005a017

文献信息

• Manufacture of arylamines
  申请人：BASF Aktiengesellschaft

  公开号：US04067903A1

  公开（公告）日：1978-01-10

  Arylamines are manufactured by reacting alcohols with amines in the presence of phosphorus-III compounds. The arylamines I manufactured by the process of the invention are intermediates for the manufacture of crop protection agents, optical brighteners, especially amino-coumarin derivatives, and dyes, especially of the xanthene, pyronine, rhodamine, oxazine, azo, triphenylmethane and diphenylmethane series.

  芳胺是通过在磷-III化合物存在下，将醇与胺反应制造而成的。根据本发明的工艺制造的芳胺是制造农作物保护剂、光亮剂（尤其是氨基香豆素衍生物）、染料（尤其是苯胺、吡啶胺、罗丹明、噁唑胺、偶氮、三苯甲烷和二苯甲烷系列）的中间体。
• Restricted Rotation in Aryl Amines. III. Preparation and Resolution of N-Succinyl-1-methylamino-2-methylnaphthalene and N-Succinyl-1-methylamino-4-chloro-2-methylnaphthalene¹
  作者：Roger Adams、A. A. Albert

  DOI：10.1021/ja01258a066

  日期：1942.6
• US4067903A
  申请人：——

  公开号：US4067903A

  公开（公告）日：1978-01-10