bis(4-hydroxymethylbenzyl)amine | 228546-60-9

• 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: bis(4-hydroxymethylbenzyl)amine
• 英文别名: ((azanediylbis(methylene))bis(4,1-phenylene))dimethanol；[4-[[[4-(Hydroxymethyl)phenyl]methylamino]methyl]phenyl]methanol
• CAS: 228546-60-9
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: JHMBEYDZFHRYHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  454.2±40.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(4-hydroxymethylbenzyl)amine 在 氢溴酸 作用下， 生成
  参考文献：
  名称：

  Triphenylphosphonium-Stoppered [2]Rotaxanes

  摘要：

  [GRAPHICS]The template directed syntheses of two [2]rotaxanes, one carrying one and the other two triphenylphosphonium stoppers, have been achieved using a threading-followed-by-stoppering approach. Either one or two benzylic bromide functions-located at the para positions of dibenzylammonium-based ions, which become encircled by dibenzo[24]crown-8 macrocycles during the initial thermodynamically controlled phases that mark the recognition events-serve as sites for nucleophilic attack by triphenylphosphine during the subsequent kinetic stages that lead to the formation of the two [2]rotaxanes.

  DOI：

  10.1021/ol990049d
• 作为产物：
  描述：

  methyl (N)-4-(((4-(methoxycarbonyl)benzyl)imino)methyl)benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 bis(4-hydroxymethylbenzyl)amine
  参考文献：
  名称：

  定向一锅法合成冠状含轮主链型聚轮烷，并控制轮烷化比。

  摘要：

  通过两种方法（A和B）成功地完成了具有冠醚轮的主链型聚轮烷的定向合成。方法A涉及直接对聚（仲铵盐）进行轮式穿线，然后用大基团封端，而方法B利用假[2]轮烷单体的加聚以促进结构的控制，即轮烷化率。

  DOI：

  10.1039/c4cc06943a

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 Synthesis of Secondary Amines from Nitriles by a User‐Friendly Cobalt Catalyst
  作者：Dipesh M. Sharma、Benudhar Punji

  DOI：10.1002/adsc.201900586

  日期：2019.9.3

  Selective hydrogenation/reductive amination of nitriles to secondary amines catalyzed by an inexpensive and user‐friendly cobalt complex, (Xantphos)CoCl2, is reported. The use of (Xantphos)CoCl2 and ammonia borane (NH3−BH3) combination affords the selective reduction of nitriles to symmetrical secondary amines, whereas the employment of (Xantphos)CoCl2 and dimethylamine borane (Me2NH−BH3) along with

  据报道，廉价和用户友好的钴络合物（Xantphos）CoCl 2催化腈选择性加氢/还原胺化成仲胺。使用（Xantphos）CoCl 2和氨硼烷（NH 3 -BH 3）组合可以将腈选择性还原为对称的仲胺，而使用（Xantphos）CoCl 2和二甲胺硼烷（Me 2 NH-BH 3）与外部胺一起产生不对称的仲胺和叔胺。该方法的一般适用性通过43种对称和不对称的仲胺和叔胺的合成来证明，这些仲胺和叔胺具有多种功能。
• Chemical On/Off Switching of Mechanically Planar Chirality and Chiral Anion Recognition in a [2]Rotaxane Molecular Shuttle
  作者：Stefano Corra、Christiaan de Vet、Jessica Groppi、Marcello La Rosa、Serena Silvi、Massimo Baroncini、Alberto Credi

  DOI：10.1021/jacs.9b00941

  日期：2019.6.12

  acid–base triggered molecular shuttling process to switch an appropriately designed rotaxane between prochiral and mechanically planar chiral forms. The mechanically planar enantiomers and their interconversion, arising from ring shuttling, have been characterized by NMR spectroscopy. We also show that the supramolecular interaction of the positively charged rotaxane with optically active anions causes an

  我们利用可逆的酸碱触发分子穿梭过程在前手性和机械平面手性形式之间切换适当设计的轮烷。由环穿梭引起的机械平面对映异构体及其相互转化已通过核磁共振光谱表征。我们还表明，带正电的轮烷与光学活性阴离子的超分子相互作用导致两种对映体共构象的数量不平衡。这一结果代表了手性分子识别的一个前所未有的例子，可以揭示对映选择性传感和催化的创新方法。
• Continuous hydrogenation reactions in a tube reactor packed with Pd/C
  作者：Nungruethai Yoswathananont、Kohei Nitta、Yumi Nishiuchi、Masaaki Sato

  DOI：10.1039/b410014j

  日期：——

  hydrogen gas through a tube reactor packed with Pd/C catalyst brings about a highly reactive and efficient hydrogenation system, which converts 4-cyanobenzaldehyde to the benzyl alcohol derivatives at 25 degrees C, and at 90 degrees C, the cyano group becomes reduced to give the corresponding amine and toluene derivatives within 2 min.

  底物溶液和氢气连续不断地流过装有Pd / C催化剂的管式反应器，产生了高反应性和高效的加氢系统，该系统可在25°C和90°C的温度下将4-氰基苯甲醛转化为苯甲醇衍生物，氰基在2分钟内还原为相应的胺和甲苯衍生物。
• Effect of Steric Barrier on the Shuttling of Rotaxane Having Crown Ether Wheel
  作者：Nobuhiro Kihara、Yoshifumi Koike、Toshikazu Takata

  DOI：10.1246/cl.2007.208

  日期：2007.2

  Rotaxanes comprising dibenzo-24-crown-8 and a symmetrical ammonium salt were desymmetrized by N-acylation. The shuttling behavior was investigated in detail. For the N,N-di-n-alkyl-type axle, the propionyl group was necessary to stop shuttling, whereas the acetyl group was bulky enough for the N,N-dibenzyl-type axle. According to the ΔS‡ term of the shuttling, the N-formyl and N-acetyl rotaxanes with an N,N-di-n-alkyl-type axle showed similar shuttling frequencies at room temperature.

  通过N-酰化使包含二苯并-24-冠-8和对称铵盐的轮烷去对称化。详细研究了穿梭行为。对于 N,N-二正烷基型轴，丙酰基是停止穿梭所必需的，而乙酰基对于 N,N-二苄基型轴来说足够大。根据穿梭的ΔS‡项，具有N,N-二正烷基型轴的N-甲酰基和N-乙酰基轮烷在室温下表现出相似的穿梭频率。