三(4-氯苄基)胺 | 36997-15-6

• 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(4-氯苄基)胺
• 英文名称: tris(4-chlorobenzyl)amine
• 英文别名: 1-(4-chlorophenyl)-N,N-bis[(4-chlorophenyl)methyl]methanamine
• CAS: 36997-15-6
• 化学式: C₂₁H₁₈Cl₃N
• 分子量: 390.74
• InChiKey: XEQVIBQVXBZKJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 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

• 作为反应物：
  描述：

  三(4-氯苄基)胺 在 ammonium hydroxide 、 1,3-二碘-5,5-二甲基海因 作用下， 反应 48.0h， 以85%的产率得到对氯苯甲腈
  参考文献：
  名称：

  在 NH3 水溶液中用 1,3-Diiodo-5,5-二甲基乙内酰脲氧化转化伯醇和伯胺、仲胺和叔胺为相应的腈类

  摘要：

  各种伯醇和伯胺、仲胺和叔胺在 60° 的氨水 (NH 3 ) 中通过 l,3-二碘-5,5-二甲基乙内酰脲 (DIH) 以良好的收率氧化并有效地转化为相应的腈C。

  DOI：

  10.1055/s-2007-967954
• 作为产物：
  描述：

  4-氯苯甲醇 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 ammonium acetate 、 碳酸氢钠 作用下， 反应 17.5h， 以77%的产率得到三(4-氯苄基)胺
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1055/s-0028-1087996

文献信息

• Highly Efficient Heterogeneous Gold-catalyzed Direct Synthesis of Tertiary and Secondary Amines from Alcohols and Urea
  作者：Lin He、Yue Qian、Ran-Sheng Ding、Yong-Mei Liu、He-Yong He、Kang-Nian Fan、Yong Cao

  DOI：10.1002/cssc.201100581

  日期：2012.4

  Urea, the white gold: The efficient synthesis of tertiary and secondary amines is achieved by heterogeneous gold‐catalyzed direct amination of stoichiometric alcohols with urea in good to excellent yields. Via a hydrogen autotransfer pathway, the reactions of primary alcohols with urea give tertiary amines exclusively, while secondary alcohols selectively afford secondary amines.

  尿素，白金：叔胺和仲胺的有效合成是通过金的多相催化尿素化学计量醇与胺的直接胺化而实现的，收率良好。通过氢自动转移途径，伯醇与尿素的反应仅产生叔胺，而仲醇选择性地提供仲胺。
• 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。
• Ruthenium-catalyzed Formation of Tertiary Amines from Nitriles and Alcohols
  作者：Saiwen Liu、Ru Chen、Guo-Jun Deng

  DOI：10.1246/cl.2011.489

  日期：2011.5.5

  A ruthenium-catalyzed tertiary-amine formation was developed using the borrowing hydrogen strategy. Various tertiary amines were obtained efficiently from nitriles and primary alcohols. Two possibl...

  使用借氢策略开发了钌催化的叔胺形成。从腈和伯醇中可以有效地获得各种叔胺。两种可能...
• Direct oxidative conversion of alcohols and amines to nitriles with molecular iodine and DIH in aq NH3
  作者：Shinpei Iida、Hideo Togo

  DOI：10.1016/j.tet.2007.05.106

  日期：2007.8

  Simple and high-yield procedures for the direct oxidative conversion of various primary alcohols, and primary, secondary, and tertiary amines to the corresponding nitriles were successfully carried out with molecular iodine in aq ammonia and 1,3-diiodo-5,5-dimethylhydantoin in aq NH3, respectively.

  用分子碘在氨水溶液和1,3-二碘-5,5-二甲基乙内酰脲中成功地进行了简单且高收率的方法，将各种伯醇以及伯，仲和叔胺直接氧化转化为相应的腈分别在NH 3水溶液中。
• One-Pot Synthesis of Symmetrical Tertiary and Secondary Amines from Carbonyl Compounds, Ammonium Carbonate and Carbon Monoxide as a Reductant
  作者：Karim Muratov、Oleg I. Afanasyev、Ekaterina Kuchuk、Sofiya Runikhina、Denis Chusov

  DOI：10.1002/ejoc.201901175

  日期：2019.10.17

  Rh‐catalyzed one‐step synthesis of tertiary and secondary amines from aldehydes and ketones, ammonium carbonate serving as nitrogen source, and carbon monoxide as a reducing agent has been developed. Aliphatic and aromatic aldehydes lead to the corresponding tertiary symmetrical amines in 69–83 % yields. Aromatic and aliphatic ketones lead to the corresponding secondary symmetrical amines which were

  已经开发了由醛和酮，碳酸铵作为氮源，一氧化碳作为还原剂的Rh催化一步和叔胺合成的叔胺和仲胺。脂肪醛和芳香醛可产生相应的叔对称胺，产率为69-83％。芳香族和脂肪族酮可产生相应的仲对称胺，产率为62-79％。