N-(benzotriazol-1-ylmethyl)-2-naphthylamine | 134627-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(benzotriazol-1-ylmethyl)-2-naphthylamine
• 英文别名: N-(1H-benzotriazol-1-ylmethyl)naphthalen-2-amine；N-(benzotriazol-1-ylmethyl)naphthalen-2-amine
• CAS: 134627-20-6
• 化学式: C₁₇H₁₄N₄
• mdl: MFCD00187823
• 分子量: 274.325
• InChiKey: BULIYNSZVODELS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(benzotriazol-1-ylmethyl)-2-naphthylamine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 3-(diphenylhydroxymethyl)-2-(methylamino)naphthalene
  参考文献：
  名称：

  Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. 17. Substitution of N-methyl-1- and N-methyl-2-naphthylamine and side-chain functionalization of o-toluidine

  摘要：

  N-Methyl-1-naphthylamine is readily converted into a range of 2-substituted derivatives in one-pot sequences, using carbon dioxide for NH protection. Similarly, N-methyl-2-naphthylamine yields 3-substituted derivatives in the first direct preparation of 2,3-disubstituted naphthalenes. The intermediate lithium carbamates are further lithiated by tert-butyllithium at the 2-position for N-methyl-1-naphthylamine and at the 3-position for N-methyl-2-naphthylamine and then reacted with an electrophile; the products undergo acid-catalyzed decarboxylation during workup. omicron-Toluidine is converted into its methyl-functionalized derivatives in a similar way, except that 2 equiv of tert-butyllithium are used for the further lithiation of the intermediate lithium carbamate.

  DOI：

  10.1021/jo00017a012
• 作为产物：
  描述：

  T406石油添加剂 、 聚合甲醛 、 2-萘胺 以 乙醇 、 水 为溶剂， 以98%的产率得到N-(benzotriazol-1-ylmethyl)-2-naphthylamine
  参考文献：
  名称：

  Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. 17. Substitution of N-methyl-1- and N-methyl-2-naphthylamine and side-chain functionalization of o-toluidine

  摘要：

  N-Methyl-1-naphthylamine is readily converted into a range of 2-substituted derivatives in one-pot sequences, using carbon dioxide for NH protection. Similarly, N-methyl-2-naphthylamine yields 3-substituted derivatives in the first direct preparation of 2,3-disubstituted naphthalenes. The intermediate lithium carbamates are further lithiated by tert-butyllithium at the 2-position for N-methyl-1-naphthylamine and at the 3-position for N-methyl-2-naphthylamine and then reacted with an electrophile; the products undergo acid-catalyzed decarboxylation during workup. omicron-Toluidine is converted into its methyl-functionalized derivatives in a similar way, except that 2 equiv of tert-butyllithium are used for the further lithiation of the intermediate lithium carbamate.

  DOI：

  10.1021/jo00017a012

文献信息

• Aerobic Oxidative Homocoupling of Aryl Amines Using Heterogeneous Rhodium Catalysts
  作者：Kenji Matsumoto、Kento Dougomori、Shohei Tachikawa、Takanori Ishii、Mitsuru Shindo

  DOI：10.1021/ol502197p

  日期：2014.9.19

  The first heterogeneous catalyzed oxidative coupling of aryl amines is reported. Aryl amines were dimerized at room temperature under air using a heterogeneous Rh/C catalyst in the presence of acids. By choosing a suitable acidic solvent, biaryl compounds and carbazoles were selectively prepared in good yields. This reaction is operationally simple and provides an efficient synthetic methodology for the preparation of biaryl diamines via oxidative C-H activation.
• Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. 17. Substitution of N-methyl-1- and N-methyl-2-naphthylamine and side-chain functionalization of o-toluidine
  作者：Alan R. Katritzky、Michael Black、Wei Qiang Fan

  DOI：10.1021/jo00017a012

  日期：1991.8

  N-Methyl-1-naphthylamine is readily converted into a range of 2-substituted derivatives in one-pot sequences, using carbon dioxide for NH protection. Similarly, N-methyl-2-naphthylamine yields 3-substituted derivatives in the first direct preparation of 2,3-disubstituted naphthalenes. The intermediate lithium carbamates are further lithiated by tert-butyllithium at the 2-position for N-methyl-1-naphthylamine and at the 3-position for N-methyl-2-naphthylamine and then reacted with an electrophile; the products undergo acid-catalyzed decarboxylation during workup. omicron-Toluidine is converted into its methyl-functionalized derivatives in a similar way, except that 2 equiv of tert-butyllithium are used for the further lithiation of the intermediate lithium carbamate.