三(3-溴苄基)胺 | 1005788-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 三(3-溴苄基)胺
• 英文名称: tris(3-bromobenzyl)amine
• 英文别名: 1-(3-bromophenyl)-N,N-bis[(3-bromophenyl)methyl]methanamine
• CAS: 1005788-48-6
• 化学式: C₂₁H₁₈Br₃N
• 分子量: 524.093
• InChiKey: BRUPPGAGJOXRSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-溴苯甲醇 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 乙酸铵 、 碳酸氢钠 作用下， 反应 17.0h， 以89%的产率得到三(3-溴苄基)胺
  参考文献：
  名称：

  通过cp *铱催化的铵盐与醇的多烷基化选择性合成仲胺和叔胺。

  摘要：

  通过Cp * Ir催化的铵盐与醇的无溶剂多烷基化反应已经实现了仲胺和叔胺的有效选择性合成：乙酸铵与醇的反应仅产生叔胺，而四氟硼酸铵的胺选择性地提供了仲胺。使用这种方法，在一锅中由四氟硼酸铵和二醇合成了五元​​和六元仲胺。

  DOI：

  10.1021/ol702522k

文献信息

• Selective Synthesis of Secondary and Tertiary Amines by Cp*Iridium-Catalyzed Multialkylation of Ammonium Salts with Alcohols
  作者：Ryohei Yamaguchi、Shoko Kawagoe、Chiho Asai、Ken-ichi Fujita

  DOI：10.1021/ol702522k

  日期：2008.1.1

  synthesis of secondary and tertiary amines has been achieved by means of Cp*Ir-catalyzed multialkylation of ammonium salts with alcohols without solvent: the reactions of ammonium acetate with alcohols gave tertiary amines exclusively, while those of ammonium tetrafluoroborate afforded secondary amines selectively. Using this method, secondary 5- and 6-membered cyclic amines were synthesized from ammonium

  通过Cp * Ir催化的铵盐与醇的无溶剂多烷基化反应已经实现了仲胺和叔胺的有效选择性合成：乙酸铵与醇的反应仅产生叔胺，而四氟硼酸铵的胺选择性地提供了仲胺。使用这种方法，在一锅中由四氟硼酸铵和二醇合成了五元​​和六元仲胺。
• A New Atom-Economical and Selective Synthesis of Secondary and Tertiary Alkylamines by Means of Cp*Iridium Complex Catalyzed Multiple N-Alkylation of Ammonium Salts with Alcohols without Solvent
  作者：Ryohei Yamaguchi、Ken-ichi Fujita、Zhu Mingwen、Shoko Kawagoe、Chiho Asai

  DOI：10.1055/s-0028-1087996

  日期：2009.4

  A new atom-economical and selective synthetic method for secondary and tertiary alkylamines has been achieved by means of (pentamethylcyclopentadienyl)iridium (Cp*Ir) complex catalyzed multiple N-alkylations of ammonium salts with primary and secondary alcohols without solvent.

  通过使用（五甲基环戊二烯基）铱（Cp*Ir）络合物催化，无需溶剂的情况下，实现了一项针对仲、叔烷基胺的新型原子经济性和选择性合成方法，即对铵盐进行多次N-烷基化反应，原料为伯、仲醇。
• Multialkylation of Aqueous Ammonia with Alcohols Catalyzed by Water-Soluble Cp*Ir−Ammine Complexes
  作者：Ryoko Kawahara、Ken-ichi Fujita、Ryohei Yamaguchi

  DOI：10.1021/ja107274w

  日期：2010.11.3

  Novel water-soluble Cp*Ir-ammine complexes have been synthesized, and a new and highly atom-economical system for the synthesis of organic amines using aqueous ammonia as a nitrogen source has been developed. With a water-soluble and air-stable Cp*Ir-ammine catalyst, [Cp*Ir(NH3)(3)][1](2), a variety of tertiary and secondary amines were synthesized by the multialkylation of aqueous ammonia with theoretical equivalents of primary and secondary alcohols. The catalyst could be recycled by a facile procedure maintaining high activity. A one-flask synthesis of quinolizidine starting with 1,5,9-nonanetriol was also demonstrated. This new catalytic system would provide a practical and environmentally benign methodology for the synthesis of various organic amines.