2-p-anisyl-1-naphthylamine | 131178-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-p-anisyl-1-naphthylamine
• 英文别名: 2-(4-Methoxyphenyl)naphthalen-1-amine
• CAS: 131178-71-7
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: FDJOKIBTMQNLFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-碘苯甲醚 、 potassium 1-naphthylamide 在 氨 作用下， 反应 3.0h， 以46%的产率得到2-p-anisyl-1-naphthylamine
  参考文献：
  名称：

  Regiochemistry of the coupling of aryl radicals with nucleophiles derived from the naphthyl system. Experimental and theoretical studies

  摘要：

  We here report the photostimulated reaction of unactivated aromatic halides with ambident nucleophiles derived from the naphthyl system such as 1- and 2-naphthylamide, 2-naphthoxide, 2-naphthalenethiolate, and 2-naphthaleneselenate ions, by the S(RN)1 mechanism of nucleophilic substitution. According to our experimental results, C-arylation in position 1 of the naphthyl moiety is the only reaction observed with 2-naphthoxide ions and it is favored over N-arylation with 1- and 2-naphthylamide ions. Heteroatom arylation is preferred over C-arylation with 2-naphthalenethiolate ions while it is the only observed reaction with 2-naphthaleneselenate ions. A theoretical study was carried out to explain the regiochemistry of the system. In competition experiments, 2-naphthalenethiolate ions proved to be 1.8 +/- 0.2 times more reactive than 2-naphthoxide ions for C-substitution toward p-anisyl radicals in liquid ammonia.

  DOI：

  10.1021/jo00002a019

文献信息

• PIERINI, ADRIANA B.;BAUMGARTNER, MARIA T.;ROSSI, ROBERTO A., J. ORG. CHEM., 56,(1991) N, C. 580-586
  作者：PIERINI, ADRIANA B.、BAUMGARTNER, MARIA T.、ROSSI, ROBERTO A.

  DOI：——

  日期：——
• Regiochemistry of the coupling of aryl radicals with nucleophiles derived from the naphthyl system. Experimental and theoretical studies
  作者：Adriana B. Pierini、Maria T. Baumgartner、Roberto A. Rossi

  DOI：10.1021/jo00002a019

  日期：1991.1

  We here report the photostimulated reaction of unactivated aromatic halides with ambident nucleophiles derived from the naphthyl system such as 1- and 2-naphthylamide, 2-naphthoxide, 2-naphthalenethiolate, and 2-naphthaleneselenate ions, by the S(RN)1 mechanism of nucleophilic substitution. According to our experimental results, C-arylation in position 1 of the naphthyl moiety is the only reaction observed with 2-naphthoxide ions and it is favored over N-arylation with 1- and 2-naphthylamide ions. Heteroatom arylation is preferred over C-arylation with 2-naphthalenethiolate ions while it is the only observed reaction with 2-naphthaleneselenate ions. A theoretical study was carried out to explain the regiochemistry of the system. In competition experiments, 2-naphthalenethiolate ions proved to be 1.8 +/- 0.2 times more reactive than 2-naphthoxide ions for C-substitution toward p-anisyl radicals in liquid ammonia.