benzylamine BH3 adduct | 4856-92-2

• 英文名称: benzylamine BH3 adduct
• 英文别名: benzylamine borane；benzylamine-borane
• CAS: 4856-92-2
• 化学式: C₇H₁₂BN
• 分子量: 120.99
• InChiKey: IAQCZRCRKKYKRQ-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：

  benzylamine BH3 adduct 在 盐酸 、 水 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 硼酸
  参考文献：
  名称：

  Bell, Kevin E.; Kelly, Henry C., Inorganic Chemistry, 1992, vol. 31, # 12, p. 2665 - 2667

  摘要：

  DOI：
• 作为产物：
  描述：

  苄胺 、 sodium tetrahydroborate 在 水 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以99%的产率得到benzylamine BH3 adduct
  参考文献：
  名称：

  胺硼烷具有硼烷不兼容的功能：在选择性胺保护和表面功能化中的应用

  摘要：

  描述了用便宜且容易获得的硼氢化钠，碳酸氢钠，水和所需的胺的胺-硼烷的第一种常规开瓶合成。甚至具有硼烷反应性官能团的胺，例如...

  DOI：

  10.1039/c6cc06031e

文献信息

• Direct preparation and structure determination of tertiary and secondary amine boranes from primary or secondary amine boranes
  作者：Amal Shibli、Hijazi Abu Ali、Israel Goldberg、Morris Srebnik

  DOI：10.1016/j.jorganchem.2005.01.059

  日期：2005.4

  New secondary and tertiary amine borane derivatives were prepared in a one-pot reaction starting from primary amine boranes. The reaction involves treatment of an amine borane with 2 equivalents of s-BuLi at −78 °C. In general, mixtures of mono and di metallated products were obtained. Alkyl iodides and benzyl chloride reacted with the lithiated amine, but aldehydes and ketones were reduced. Conversion

  一锅反应从伯胺硼烷开始制备新的仲胺和叔胺硼烷衍生物。该反应涉及在-78°C下用2当量的s -BuLi处理胺基硼烷。通常，获得单和双金属化产物的混合物。烷基碘和苄基氯与锂化的胺反应，但醛和酮被还原。如通过NMR确定的，转化率高，但是在色谱分离后获得中至低产率，这可能是由于在二氧化硅上的分解所致。获得了化合物3a，3b和3c的晶体结构。
• Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes
  作者：Yu-Qi Miao、Jia-Xin Kang、Yan-Na Ma、Xuenian Chen

  DOI：10.1039/d1gc01157j

  日期：——

  Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of

  在此，描述了使用容易获得的胺-硼烷和羧酸的光催化脱氧酰胺化方案。这种方法的特点是条件温和，收率中等至良好，易于放大，并具有多达62个带有各种取代基的官能化酰胺实例。该方法在几种药物分子的后期功能化中的应用也证明了该方法的综合耐用性。
• Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions
  作者：Hao Song、Yao Xiao、Zhuohua Zhang、Wanjin Xiong、Ren Wang、Liangcheng Guo、Taigang Zhou

  DOI：10.1021/acs.joc.1c02413

  日期：2022.1.7

  efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine–BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to

  报道了一种简单而有效的铜催化腈选择性转移氢化为伯胺-硼烷和仲胺与恶氮硼烷-BH 3 配合物的方法。通过切换溶剂和铜催化剂在温和条件下实现选择性控制。通过该策略以高选择性和高达 95% 的产率合成了 30 多种伯胺-硼烷和 40 种仲胺。该策略应用于以89% 的收率合成15 N 标记。
• Studies on aromatic amine boranes by 11B and 1H NMR
  作者：C. Camacho、M.A. Paz-Sandoval、R. Contreras

  DOI：10.1016/s0277-5387(00)84849-4

  日期：——

  Abstract 1 H and 11 B NMR spectroscopy was applied to mono- and bisborane adducts derived from aryl-, benzyl-, phenethyl- and phenylenediamines, but no simple relationship was established between the spectroscopic data and the nature of the NB bond. Comparative studies of the affinity of aromatic amines to BH 3 by equilibria reactions may be of great value in establishing a scale of relative basicity

  摘要1 H和11 B NMR光谱用于衍生自芳基，苄基，苯乙基和苯二胺的单和双硼烷加合物，但光谱数据与NB键的性质之间没有简单的关系。通过平衡反应对芳香胺对BH 3的亲和力进行比较研究可能对建立相对碱性的规模具有重要价值。
• Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids
  作者：P. Veeraraghavan Ramachandran、Henry J. Hamann、Shivani Choudhary

  DOI：10.1021/acs.orglett.0c03184

  日期：2020.11.6

  Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities

  胺-硼烷用作直接酰胺化的两用试剂，可活化脂肪族和芳香族羧酸，随后以高达99％的收率递送胺以提供相应的酰胺。气态或低沸点胺作为硼烷络合物的输送提供了优于现有方法的主要优势。利用含有硼烷不相容官能团的胺-硼烷可以制备官能化的酰胺。提出了通过三酰氧基硼烷-胺络合物的分子间机制。