2-bromo-N-(α-naphthyl)benzylamine | 356531-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-N-(α-naphthyl)benzylamine
• 英文别名: N-(2-bromobenzyl)naphthalen-1-amine；N-[(2-bromophenyl)methyl]naphthalen-1-amine
• CAS: 356531-16-3
• 化学式: C₁₇H₁₄BrN
• 分子量: 312.209
• InChiKey: JVNOGVRLSASOEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  2-bromo-N-(α-naphthyl)benzylamine 在 C₁₈H₃₃P*BF₃*FH 、 palladium diacetate 、 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 mineral oil 为溶剂， 反应 22.5h， 生成 N-methyl-5,6-dihydrobenzo[c]phenanthridine
  参考文献：
  名称：

  Synthesis of N -methyl-5,6-dihydrobenzo[ c ]phenanthridine and its sp 3 C(6)–H bond functionalization via oxidative cross-dehydrogenative coupling reactions

  摘要：

  An expeditious route involving a Pd-catalyzed intramolecular biaryl-coupling for the synthesis of the N-methyl-5,6-dihydrobenzo[c]phenanthridine scaffold has been developed. For the first time, we herein report the sp(3) C(6)-H functionalization of this heterocyclic scaffold through DDQ-mediated cross-dehydrogenative coupling reactions with nitroalkanes, dialkyl malonates, alkynes, dialkyl phosphites, carbonyl compounds, pyrrole, and indoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.018
• 作为产物：
  描述：

  1-萘胺 、 邻溴苯甲醛 在 indium(III) chloride 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 为溶剂， 反应 17.25h， 以94%的产率得到2-bromo-N-(α-naphthyl)benzylamine
  参考文献：
  名称：

  Synthesis of N -methyl-5,6-dihydrobenzo[ c ]phenanthridine and its sp 3 C(6)–H bond functionalization via oxidative cross-dehydrogenative coupling reactions

  摘要：

  An expeditious route involving a Pd-catalyzed intramolecular biaryl-coupling for the synthesis of the N-methyl-5,6-dihydrobenzo[c]phenanthridine scaffold has been developed. For the first time, we herein report the sp(3) C(6)-H functionalization of this heterocyclic scaffold through DDQ-mediated cross-dehydrogenative coupling reactions with nitroalkanes, dialkyl malonates, alkynes, dialkyl phosphites, carbonyl compounds, pyrrole, and indoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.018

文献信息

• Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from <i>N</i>-(<i>ortho</i>-Halobenzyl)arylamines: Regiochemical and Mechanistic Analysis
  作者：María E. Budén、Viviana B. Dorn、Martina Gamba、Adriana B. Pierini、Roberto A. Rossi

  DOI：10.1021/jo9025918

  日期：2010.4.2

  The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(ortho-halobenzyl)arylamines has been found to proceed in very good to excellent yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of ortho-halobenzylchlorides with different arylamines. The reaction of the anions of a diverse set of N-(ortho-halobenzyl)arylamines was studied, and the methodology was extended to the synthesis of tri-spheridine, a natural product, in very good yield. In order to explain the regiochemical outcome or these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.
• Synthesis of N -methyl-5,6-dihydrobenzo[ c ]phenanthridine and its sp 3 C(6)–H bond functionalization via oxidative cross-dehydrogenative coupling reactions
  作者：Adriana Romo-Pérez、Luis D. Miranda、Abraham García

  DOI：10.1016/j.tetlet.2015.10.018

  日期：2015.12

  An expeditious route involving a Pd-catalyzed intramolecular biaryl-coupling for the synthesis of the N-methyl-5,6-dihydrobenzo[c]phenanthridine scaffold has been developed. For the first time, we herein report the sp(3) C(6)-H functionalization of this heterocyclic scaffold through DDQ-mediated cross-dehydrogenative coupling reactions with nitroalkanes, dialkyl malonates, alkynes, dialkyl phosphites, carbonyl compounds, pyrrole, and indoles. (C) 2015 Elsevier Ltd. All rights reserved.