4-hydroxy-(benzeneethanamine)-N-(phenylmethylene)

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-(benzeneethanamine)-N-(phenylmethylene)
• 英文别名: N-benzylidenetyramine；4-[2-(Benzylideneamino)ethyl]phenol
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: MXBLMHZZTHPSFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-(benzeneethanamine)-N-(phenylmethylene) 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4-[2-[Benzyl-[2-hydroxy-2-[3-(hydroxymethyl)-4-phenylmethoxyphenyl]ethyl]amino]ethyl]phenol
  参考文献：
  名称：

  A multivalent approach to the discovery of long-acting β2-adrenoceptor agonists for the treatment of asthma and COPD

  摘要：

  A multivalent approach was applied to the design of long-acting inhaled beta(2)-adrenoceptor agonists. A series of dimeric arylethanolamines based on the short acting beta(2)-adrenoceptor agonist albuterol were prepared, varying the nature and length of the linker between the basic nitrogens. None of the C-2-symmetric dimers demonstrated increased potency, however dimer 5j, derived from 4-phenethylamine, was found to have increased binding Potency in vitro relative to the parent monomer. Optimization of this structure led to the identification of 22 (milveterol) which demonstrates high potency in vitro and long duration of action in a guinea pig model of bronchoprotection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.072
• 作为产物：
  描述：

  对羟基苯乙胺 、 苯甲醛 反应 24.0h， 以72%的产率得到4-hydroxy-(benzeneethanamine)-N-(phenylmethylene)
  参考文献：
  名称：

  N-亚苄基苯胺的合成及分子间相互作用

  摘要：

  摘要 本文研究了N-亚苄基苯胺分子之间的合成和分子间相互作用。N-(4-硝基亚苄基)酪胺的晶体结构显示出在偶氮甲碱和酚羟基之间具有分子间OH⋯N氢键的锯齿形链中的分子组织。这些链通过 CH⋯O 氢键连接在一起以生成层，这些层通过 CH⋯O、π⋯π 和 NO2⋯π 相互作用连接。

  DOI：

  10.1016/j.molstruc.2016.08.035

文献信息

• Sodium borohydride on wet clay: Solvent-free reductive amination of carbonyl compounds using microwaves
  作者：Rajender S. Varma、Rajender Dahiya

  DOI：10.1016/s0040-4020(98)00326-3

  日期：1998.6

  A solvent-free reductive amination of carbonyl compounds by wet montmorillonite K 10 clay supported sodium borohydride is described; microwave irradiation facilitates the procedure.

  描述了通过湿蒙脱石K 10粘土负载的硼氢化钠对羰基化合物进行无溶剂还原胺化反应。微波辐射使该过程变得容易。
• Highly efficient iron phthalocyanine catalyzed oxidative synthesis of imines from alcohols and amines
  作者：Manju Bala、Praveen Kumar Verma、Neeraj Kumar、Upendra Sharma、Bikram Singh

  DOI：10.1139/cjc-2012-0399

  日期：2013.8

  An efficient iron phthalocyanine catalyzed method was developed for direct oxidative coupling of alcohols with amines to afford corresponding imines. The present protocol is applicable to various substituted aromatic and aliphatic alcohols and amines. The reaction is believed to proceed via activation of alcohols by iron phthalocyanines through Lewis acid–base interaction to form aldehydes, which by nucleophilic attack of amines are converted into the corresponding imines.

  开发了一种高效的铁酞菁催化方法，用于直接氧化偶联醇和胺，生成相应的亚胺。该方法适用于各种取代芳香族和脂肪族醇和胺。该反应被认为通过铁酞菁对醇的活化，通过路易斯酸碱相互作用形成醛，然后通过胺的亲核攻击转化为相应的亚胺。
• Synthesis and intermolecular interactions of N-benzylidenetyramines
  作者：Mauricio Maldonado、Adrián Pérez-Redondo、Rodolfo Quevedo

  DOI：10.1016/j.molstruc.2016.08.035

  日期：2017.1

  Abstract In this paper, the synthesis and intermolecular interactions between N-benzylidenetyramine molecules were investigated. The crystal structure of N-(4-nitrobenzylidene)tyramine shows a molecular organization in zigzag chains with intermolecular O-H⋯N hydrogen bonds between the azomethine and phenolic hydroxyl groups. Those chains are held together by C-H⋯O hydrogen bonds to generate layers

  摘要 本文研究了N-亚苄基苯胺分子之间的合成和分子间相互作用。N-(4-硝基亚苄基)酪胺的晶体结构显示出在偶氮甲碱和酚羟基之间具有分子间OH⋯N氢键的锯齿形链中的分子组织。这些链通过 CH⋯O 氢键连接在一起以生成层，这些层通过 CH⋯O、π⋯π 和 NO2⋯π 相互作用连接。
• 无定型低软化点邻苯二甲腈单体、邻苯二甲腈树脂及其制备方法与用途
  申请人：四川大学

  公开号：CN115557854A

  公开（公告）日：2023-01-03

  本发明公开了无定型低软化点邻苯二甲腈单体、邻苯二甲腈树脂及其制备方法与应用，无定型低软化点邻苯二甲腈单体的结构通式如下： 进一步以无定型低软化点邻苯二甲腈单体为原料，通过自固化制备得到邻苯二甲腈树脂。该无定型低软化点的邻苯二甲腈单体还可作为芳氰基单体的改性剂。本发明所述邻苯二甲腈单体呈现出无定型性，并具有较低的软化点，可实现优异的热加工和热机械加工，有望为芳杂环高性能聚合物的设计提供新的启示。
• N-Benzylazacyclophane synthesis via aromatic Mannich reaction
  作者：Christian Díaz-Oviedo、Rodolfo Quevedo

  DOI：10.1016/j.tetlet.2014.10.023

  日期：2014.11

  A new method for synthesizing phenolic N-benzylazacyclophanes starting from tyramine is presented here. Computational calculations showed that macrocyclization is favored by the formation of hydrogen bond-based templates; these templates are not affected by including benzyl groups in the nitrogen atom of the tyramine moiety. The results showed that N-benzyl groups with electron-donating substituents have more nucleophilic nitrogen atoms, thereby favoring macrocyclization, while electron-withdrawing groups favor polymerization. (C) 2014 Elsevier Ltd. All rights reserved.