三(4-三氟甲基苄基)胺 | 1005788-49-7

• 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(4-三氟甲基苄基)胺
• 英文名称: tris(4-trifluoromethylbenzyl)amine
• 英文别名: Tris[4-(trifluoromethyl)benzyl]amine；1-[4-(trifluoromethyl)phenyl]-N,N-bis[[4-(trifluoromethyl)phenyl]methyl]methanamine
• CAS: 1005788-49-7
• 化学式: C₂₄H₁₈F₉N
• 分子量: 491.399
• InChiKey: MNOULCXHBSLAKH-UHFFFAOYSA-N

物化性质

• 沸点：
  422.5±40.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(1,3-dibenzyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)benzimidamide 、 三(4-三氟甲基苄基)胺 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 caesium carbonate 作用下， 以70 %的产率得到1,3-dibenzyl-7-phenyl-5-(4-(trifluoromethyl)phenyl)-5,6-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Oxidative C(sp³)−N Cleavage Cascade Cyclization of N‐Uracil Amidines and Tertiaryamines: Switchable Divergent Synthesis of Functionalized Pyrimidouracils and Dihydropyrimidouracils

  摘要：

  摘要 首次描述了通过氧化 C(sp3)-N 裂解级联环化反应，从 N-尿嘧啶脒和叔胺出发，分歧合成二氢嘧啶尿嘧啶和嘧啶尿嘧啶衍生物。通过选择不同的氧化条件，这种转化可以形成新的 C(sp3)-N 和 C(sp2)-N 键。这种方法的特点包括可调的产物选择性、优异的化学选择性、易得的起始材料、广泛的底物范围、对官能团的良好耐受性以及中等到较高的产率。

  DOI：

  10.1002/ejoc.202300653
• 作为产物：
  描述：

  4-(三氟甲基)苄醇 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 ammonium acetate 、 碳酸氢钠 作用下， 反应 17.5h， 以84%的产率得到三(4-三氟甲基苄基)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

• 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。
• Catalyst-Dependent Selective Hydrogenation of Nitriles: Selective Synthesis of Tertiary and Secondary Amines
  作者：Yasunari Monguchi、Masahiro Mizuno、Tomohiro Ichikawa、Yuki Fujita、Eri Murakami、Tomohiro Hattori、Tomohiro Maegawa、Yoshinari Sawama、Hironao Sajiki

  DOI：10.1021/acs.joc.7b01823

  日期：2017.10.20

  under ordinary hydrogen gas pressure to afford the corresponding tertiary amines. However, the use of rhodium on carbon (Rh/C) led to the highly selective generation of secondary amines. Hydrogenation of aromatic nitriles and cyclohexanecarbonitrile selectively produced secondary amines in the presence of either Pd/C or Rh/C.

  在钯/碳（Pd / C）作为催化剂的存在下，脂环腈在环己烷中的氢化在25-60°C的氢气压力下有效地进行，得到相应的叔胺。但是，使用碳载铑（Rh / C）可以高度选择性地生成仲胺。在Pd / C或Rh / C的存在下，芳族腈和环己烷腈的氢化选择性生成仲胺。
• 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.
• In-Water Dehydrative Alkylation of Ammonia and Amines with Alcohols by a Polymeric Bimetallic Catalyst
  作者：Hidetoshi Ohta、Yoshinari Yuyama、Yasuhiro Uozumi、Yoichi M. A. Yamada

  DOI：10.1021/ol201422s

  日期：2011.8.5

  An in-water dehydrative alkylation with a novel heteroblmetallic polymeric catalyst Is described. Thus, a boron iridium heteroblmetallic polymeric catalyst was prepared by ionic convolution of a poly(catechol borate) and an Iridium complex. The alkylation of ammonia and amines with alcohols, alkylating agents, was performed with 1 mol % Ir of the heterogeneous catalyst In water without the use of organic solvents under aerobic conditions to give the corresponding alkylated amines.