2-(methylamino)-3-<(4-methylphenyl)hydroxymethyl>naphthalene | 134627-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(methylamino)-3-<(4-methylphenyl)hydroxymethyl>naphthalene
• 英文别名: [3-(Methylamino)naphthalen-2-yl]-(4-methylphenyl)methanol
• CAS: 134627-27-3
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: KYURPZAIOJIONT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(benzotriazol-1-ylmethyl)-2-naphthylamine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 2-(methylamino)-3-<(4-methylphenyl)hydroxymethyl>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

文献信息

• 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.