indoline-borane | 1104738-20-6

• 英文名称: indoline-borane
• 英文别名: (indoline)BH3
• CAS: 1104738-20-6
• 化学式: C₈H₁₂BN
• 分子量: 133.001
• InChiKey: MMCCEQCPJAOGAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  indoline-borane 以 neat (no solvent) 为溶剂， 生成 1-borylindoline
  参考文献：
  名称：

  The dehydrogenation of combined organic and inorganic hydrogen-storage carriers

  摘要：

  通过将以内热方式释放 H2 的载体与以放热方式释放 H2 的载体结合起来，可以创建一个热平衡的 H2 储存系统。在这里，我们描述了两种 H2 载体的组合，其中两种载体都通过脱氢而不是水解来释放 H2。测试的内热载体是杂环有机液体，而放热载体是胺硼烷化合物。我们探讨了两种载体化学结合在一起或仅仅物理混合在一起的方案。在这两种方案中，放热载体通过化学作用影响内热载体的杂环或通过降低异相脱氢催化剂的活性来抑制内热载体。

  DOI：

  10.1139/v10-026
• 作为产物：
  描述：

  吲哚啉 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以85%的产率得到indoline-borane
  参考文献：
  名称：

  Production of H₂ from Combined Endothermic and Exothermic Hydrogen Carriers

  摘要：

  One of the major limitations to the use of fuel cell systems in vehicular transportation is the lack of hydrogen storage systems that have the required hydrogen storage density and moderate enthalpy of dehydrogenation. Organic liquid H-2 carriers that release H-2 endothermically are easier to handle with existing infrastructure because they are liquids, but they have low storage densities and their endothermicity consumes energy in the vehicle. On the other hand, inorganic solid H-2 carriers that release H-2 exothermically have greater storage densities but are unpumpable solids. This paper explores combinations of an endothermic carrier and an exothermic carrier, where the exothermic carrier provides some or all of the necessary heat required for dehydrogenation to the endothermic system, and the endothermic carrier serves as a solvent for the exothermic carrier. The two carriers can be either physically mixed or actually bonded to each other. To test the latter strategy, a number of chemically bound N-heterocycle:BH3 adducts were synthesized and in turn tested for their ability to release H-2 by tandem hydrolysis of the BH3 moiety and dehydrogenation of the heterocycle. To test the strategy of physically mixing two carriers, the hydrolysis of a variety of amine-boranes (H3N:BH3, Me2HN:BH3, Et3N:BH3) and the catalytic dehydrogenation of indoline were carried out together.

  DOI：

  10.1021/ja806721s

文献信息

• Reductive amination of ketones/aldehydes with amines using BH₃N(C₂H₅)₃ as a reductant
  作者：Qizhuang Zou、Fei Liu、Tianxiang Zhao、Xingbang Hu

  DOI：10.1039/d1cc02618f

  日期：——

  first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination.

  在此，我们报告了使用 BH 3 N(C 2 H 5 ) 3作为催化剂和还原剂在温和条件下用胺有效还原胺化酮/醛的第一个例子，以优异的产率提供各种叔胺和仲胺。机理研究表明，BH 3 N(C 2 H 5 ) 3具有促进亚胺和亚胺形成以及在还原胺化中作为还原剂的双重作用。
• Revisiting the reduction of indoles by hydroboranes: A combined experimental and computational study
  作者：Arumugam Jayaraman、Henry Powell-Davies、Frédéric-Georges Fontaine

  DOI：10.1016/j.tet.2019.02.048

  日期：2019.4

  A combined experimental and density functional computational study was used to probe the mechanism for the reduction of indoles using simple borane BH3·DMS (DMS = dimethyl sulfide). Experimental and computational studies all steer to the formation of the reduced species 1-BH2-indolines as the resting state for this reaction, as opposed to the historically presumed formation of the unreduced 1-BH2-indoles

  结合实验和密度泛函计算研究，使用简单的硼烷BH 3 ·DMS（DMS =二甲基硫醚）探讨了吲哚还原的机理。实验和计算研究都转向形成还原态的1-BH 2-二氢吲哚，作为该反应的静止状态，这与在质子添加之前未还原的1-BH 2-吲哚的历史推测形成相反。源形成最终的产品indolines。此外，观察到分子H 2生成并在反应中消耗。计算提出硼氢化然后原基去硼酸盐化是形成实验观察到的主要中间体1-BH 2二氢吲哚的非常合理的机理。对于反应中的H 2消耗，计算表明通过双（3-吲哚基）硼烷中间体可进行H 2的沮丧的Lewis对型杂化裂解。