benzyl-4-hydroxymethylbenzylamine | 217298-63-0

• 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: benzyl-4-hydroxymethylbenzylamine
• 英文别名: (4-((benzylamino)methyl)phenyl)methanol；[4-[(Benzylamino)methyl]phenyl]methanol；[4-[(benzylamino)methyl]phenyl]methanol
• CAS: 217298-63-0
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: SLZFJBJFOLMXKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl-4-hydroxymethylbenzylamine 在 氯化亚砜 作用下， 生成 benzyl-4-chloromethylbenzylammonium chloride
  参考文献：
  名称：

  Ashton, Peter R.; Glink, Peter T.; Martinez-Diaz, M.-Victoria, Angewandte Chemie, 1996, vol. 108, # 17, p. 2058 - 2061

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 4-((benzylamino)methyl)benzoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 benzyl-4-hydroxymethylbenzylamine
  参考文献：
  名称：

  Ashton, Peter R.; Glink, Peter T.; Martinez-Diaz, M.-Victoria, Angewandte Chemie, 1996, vol. 108, # 17, p. 2058 - 2061

  摘要：

  DOI：

文献信息

• 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。
• Selective Self-Assembly and Acid–Base Controlled De-/Rethreading of Pseudorotaxanes Constructed Using Multiple Recognition Motifs
  作者：Peter R. Ashton、Roberto Ballardini、Vincenzo Balzani、Matthew C. T. Fyfe、M. Teresa Gandolfi、M.-Victoria Martínez-Díaz、Marco Morosini、Cesare Schiavo、Kazusato Shibata、J. Fraser Stoddart、Andrew J. P. White、David J. Williams

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2332::aid-chem2332>3.3.co;2-j

  日期：1998.11.2

  The selective self-assembly of a threadlike tetracation, containing two dialkylammonium (NH2+) centers and a 4,4'bipyridinium (bpym(2+)) unit, with an assortment of macrocyclic polyethers has been investigated. Spectroscopic studies, supported by X-ray crystallographic analyses, have demonstrated the formation of pseudorotaxanes between the thread and the macrocyclic polyethers. In particular, the macrocyclic polyethers dibenzo[24]crown-8 (DB24C8) and bis-p-phenylene[34]crown-10 (BPP34C10) associate selectively with the thread's NH2+ and bpym(2+) units, respectively, to generate novel multicomponent pseudorotaxane and pseudopolyrotaxane superarchitectures as a consequence of hydrogen-bonding and charge-transfer interactions. BPP34C10's preference for bpym(2+) units is shared by several of its dinaphtho-containing crown-l0 congeners, which self-assemble with the tetracationic thread to produce [2]pseudorotoxanes in which the bpym(2+) moiety is encircled by the macrocyclic polyether. The reversible acid - base controlled de/rethreading of [n]pseudorotaxanes based on the multifunctional tetracationic thread has also been studied by H-1 NMR, absorption, and fluorescence spectroscopies. Only one DB24CS macrocycle is ejected from a [3]pseudorotaxane-created from the tetracationic thread and two DB24C8 molecules-when both of its DB24CS-encircled NH; centers are deprotonated with base, leading to a [2]pseudorotaxane whose bpym(2+) unit is associated with the remaining DB24C8 macroring, The [3]pseudorotaxane is reestablished upon reprotonation of the thread with a stoichiometric amount of acid. Treatment of this species with an excess of acid causes protonation of the DB24C8 macrorings, which are completely dethreaded thereafter, Again, the dethreading process can be reversed upon neutralization of the surplus acid with base, Addition of dicyclohexano[24] crown-8 (DCy24C8) to a solution of the [3]pseudorotaxane induces the dethreading of one of the two DB24C8 macrocycles, so that a [4]pseudorotaxane is produced in which the tetracation's NH2+ and bpym(2+) units are encircled by DCy24C8 and DB24C8 macrorings, respectively Reversible acid- base de-/rethreading processes have also been observed for [2]pseudorotaxanes bearing the dinaphtho-containing crown-10s.