tris(2-bromobenzyl)amine

• 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: tris(2-bromobenzyl)amine
• 英文别名: 1-(2-bromophenyl)-N,N-bis[(2-bromophenyl)methyl]methanamine
• 化学式: C₂₁H₁₈Br₃N
• 分子量: 524.093
• InChiKey: IMRMEYYSPHLBKW-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

• 作为反应物：
  描述：

  tris(2-bromobenzyl)amine 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 生成 三苄胺
  参考文献：
  名称：

  Synthesis and structural studies of tris-2-chlorobenzylamine and tris-2-bromobenzylamine

  摘要：

  三-2-氯和 2-溴三苄胺分别由氨水和乙醇中的 2-氯苄基氯和 2-溴苄基溴制备而成。重结晶得到了每种产物的无色立方体。晶体结构均为空间群 P $$\bar 1$$$，且结构相同。三-2-氯化合物 1 的 a = 7.4226(5)埃，b = 9.0825(7)埃，c = 14.529(1)埃，α = 78.279(1)∘，β = 82.389(1)∘，γ = 84.661(1)∘，V = 948.41(12)埃3，Z = 2，d calc = 1.368 Mg/m3。三-2-溴类似物 2 的 a = 7.6569(11)埃、b = 9.0922(13)埃、c = 14.614(2)埃、α = 79.286(2)∘、β = 81.777(2)∘、γ = 85.401(2)∘、V = 987.9(2)埃3（Z = 2）、d calc = 1.762 Mg/m3。在-78∘C 的四氢呋喃中使用正丁基锂进行的锂-卤素交换实验表明，三-2-氯化合物没有发生交换，但三-2-溴类似物发生了交换，在淬火和升温后生成了三苄胺。

  DOI：

  10.1007/s10870-005-2954-5
• 作为产物：
  描述：

  2-溴溴苄 在 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以97%的产率得到tris(2-bromobenzyl)amine
  参考文献：
  名称：

  Synthesis and structural studies of tris-2-chlorobenzylamine and tris-2-bromobenzylamine

  摘要：

  三-2-氯和 2-溴三苄胺分别由氨水和乙醇中的 2-氯苄基氯和 2-溴苄基溴制备而成。重结晶得到了每种产物的无色立方体。晶体结构均为空间群 P $$\bar 1$$$，且结构相同。三-2-氯化合物 1 的 a = 7.4226(5)埃，b = 9.0825(7)埃，c = 14.529(1)埃，α = 78.279(1)∘，β = 82.389(1)∘，γ = 84.661(1)∘，V = 948.41(12)埃3，Z = 2，d calc = 1.368 Mg/m3。三-2-溴类似物 2 的 a = 7.6569(11)埃、b = 9.0922(13)埃、c = 14.614(2)埃、α = 79.286(2)∘、β = 81.777(2)∘、γ = 85.401(2)∘、V = 987.9(2)埃3（Z = 2）、d calc = 1.762 Mg/m3。在-78∘C 的四氢呋喃中使用正丁基锂进行的锂-卤素交换实验表明，三-2-氯化合物没有发生交换，但三-2-溴类似物发生了交换，在淬火和升温后生成了三苄胺。

  DOI：

  10.1007/s10870-005-2954-5

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。
• Synthesis and Catalytic Activity of Atrane‐type Hard and Soft Lewis Superacids with a Silyl, Germyl, or Stannyl Cationic Center
  作者：Daiki Tanaka、Akihito Konishi、Makoto Yasuda

  DOI：10.1002/asia.202100873

  日期：2021.10.18

  group 14 center are synthesized and characterized; all act as hard and soft Lewis superacids (LSAs) with high catalytic activity. The framework stabilizes the localized positive charge, facilitating highly coordinated states of 1E+. Hard and soft LSAs have potential roles in organic synthesis.

  合成并表征了具有阳离子基团14中心的莠去烷型分子1E +；所有这些都充当具有高催化活性的硬和软路易斯超强酸 (LSA)。该框架稳定了局部正电荷，促进了1 E + 的高度协调状态。硬和软 LSA 在有机合成中具有潜在作用。
• Synthesis, structure and properties of trivalent and pentavalent tricarbabismatranes
  作者：Shigeru Shimada、Shuang-Feng Yin、Yoong-Kee Choe

  DOI：10.1039/d2cc00751g

  日期：——

  were synthesized by the reaction of N(CH22-LiC6H4})3 with BiCl3 and subsequent reaction with XeF2, respectively. The trivalent bismatrane was easily oxidized by air, while the pentavalent bismatrane difluoride was relatively stable to air. A similar pentavalent bismatrance dichloride was prone to C–Cl bond reductive elimination even at room temperature.

  通过N(CH 2 2-LiC 6 H 4 }) 3与BiCl 3的反应以及随后与XeF 2的反应，分别合成了第一个三价和五价三碳比斯马烷。三价双氟双胍易被空气氧化，而五价双氟双氟醚对空气相对稳定。即使在室温下，类似的五价双氯化物也易于发生 C-Cl 键还原消除。
• 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.
• Jackson; Whithe, American Chemical Journal, 1880, vol. 2, p. 317,319
  作者：Jackson、Whithe

  DOI：——

  日期：——