N-benzyl-4-(o-bromophenyl)butylamine | 169963-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-4-(o-bromophenyl)butylamine
• 英文别名: Benzenebutanamine, 2-bromo-N-(phenylmethyl)-；N-benzyl-4-(2-bromophenyl)butan-1-amine
• CAS: 169963-60-4
• 化学式: C₁₇H₂₀BrN
• 分子量: 318.257
• InChiKey: MLPMPKMVOCZTFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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-benzyl-4-(o-bromophenyl)butylamine 在 四(三苯基膦)钯 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以89%的产率得到1-benzyl-2,3,4,5-tetrahydro-1H-1-benzazepine
  参考文献：
  名称：

  分子内钯催化的芳基胺化和芳基酰胺化

  摘要：

  在用钯催化剂和合适的碱处理后，芳族卤化物进行分子内取代以形成五元，六元和七元环。以类似的方式，将具有侧基酰胺或磺酰胺的芳基卤化物环化以形成五元和六元环。

  DOI：

  10.1016/0040-4020(96)00266-9
• 作为产物：
  描述：

  邻碘溴苯 在 palladium diacetate titanium(IV) isopropylate 、 sodium tetrahydroborate 、 四丁基氯化铵 、 碳酸氢钠 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N-benzyl-4-(o-bromophenyl)butylamine
  参考文献：
  名称：

  Synthesis of 2-substituted 1-benzyl-2,3,4,5-tetrahydro-1-benzazepines by palladium catalysis. Observation of a competitive β-hydride elimination pathway

  摘要：

  A synthetic route to 1-benzyl-tetrahydro-1-benzazepine is reported, which also permits access to analogous structures with alkyl and aryl substituents at position-2 of the aliphatic ring. Palladium catalysis is utilized in two of the three steps, constructing the seven-membered rings effectively from 2-bromoiodobenzene. Competitive P-hydride elimination was observed in the attempted carbon-nitrogen bond formation with a sterically bulky substrate (when R = tert-butyl). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00676-2

文献信息

• Intramolecular palladium-catalyzed aryl amination and aryl amidation
  作者：John P. Wolfe、Roger A. Rennels、Stephen L. Buchwald

  DOI：10.1016/0040-4020(96)00266-9

  日期：1996.5

  treatment with a palladium catalyst and a suitable base, aromatic halides undergo intramolecular substitution to form five, six, and seven-membered rings. In a similar fashion aryl halides with pendant amides or sulfonamides are cyclized to form five and six-membered rings.

  在用钯催化剂和合适的碱处理后，芳族卤化物进行分子内取代以形成五元，六元和七元环。以类似的方式，将具有侧基酰胺或磺酰胺的芳基卤化物环化以形成五元和六元环。
• Guram, Anil S.; Rennels, Roger A.; Buchwald, Stephen L., Angewandte Chemie, 1995, vol. 107, # 12, p. 1456 - 1459
  作者：Guram, Anil S.、Rennels, Roger A.、Buchwald, Stephen L.

  DOI：——

  日期：——
• Synthesis of 2-substituted 1-benzyl-2,3,4,5-tetrahydro-1-benzazepines by palladium catalysis. Observation of a competitive β-hydride elimination pathway
  作者：Maryiam Qadir、Rachael E. Priestley、Thomas W.D.F. Rising、Thomas Gelbrich、Simon J. Coles、Michael B. Hursthouse、Peter W. Sheldrake、Neil Whittall、K.K.(Mimi) Hii

  DOI：10.1016/s0040-4039(03)00676-2

  日期：2003.4

  A synthetic route to 1-benzyl-tetrahydro-1-benzazepine is reported, which also permits access to analogous structures with alkyl and aryl substituents at position-2 of the aliphatic ring. Palladium catalysis is utilized in two of the three steps, constructing the seven-membered rings effectively from 2-bromoiodobenzene. Competitive P-hydride elimination was observed in the attempted carbon-nitrogen bond formation with a sterically bulky substrate (when R = tert-butyl). (C) 2003 Elsevier Science Ltd. All rights reserved.