2-ethoxybenzylamine hydrochloride | 90642-62-9

• 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: 2-ethoxybenzylamine hydrochloride
• 英文别名: (2-ethoxyphenyl)methanamine hydrochloride；(2-ethoxyphenyl)methanamine hydrpochloride；2-Aethoxy-benzylamin; Hydrochlorid；(2-ethoxyphenyl)methanamine;hydrochloride
• CAS: 90642-62-9
• 化学式: C₉H₁₃NO*ClH
• mdl: MFCD07783702
• 分子量: 187.669
• InChiKey: CRFNBYQJSHZZHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  35.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙氧基苯甲酰胺 在 [(aNHC)KN(SiMe₃)₂]₂ 、 频那醇硼烷 、 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲苯 、 乙醚 、 水 为溶剂， 反应 13.0h， 以77%的产率得到2-ethoxybenzylamine hydrochloride
  参考文献：
  名称：

  使用基于NHC的异常钾络合物实现无过渡金属的伯酰胺催化还原：将亲核性与Lewis酸性活化相结合

  摘要：

  异常的基于N-杂环卡宾（aNHC）的钾络合物用作无过渡金属的催化剂，用于在环境条件下将伯酰胺还原为相应的伯胺。仅催化剂的2mol％负载显示出广泛的底物范围，包括具有优异的官能团耐受性的芳族，脂族和杂环伯酰胺。该方法适用于手性酰胺的还原，并用于克级的药学上有价值的前体的合成。在机理研究过程中，通过光谱技术分离和表征了几种中间体，并且通过单晶XRD表征了一种催化中间体。定义明确的催化剂和可分离的中间体，以及一些化学计量的原位实验 NMR实验和DFT研究帮助我们勾画出了该还原过程的机理途径，从而揭示了催化剂的双重作用，包括aNHC的亲核活化以及K离子的Lewis酸性活化。

  DOI：

  10.1039/c9sc05953a

文献信息

• Ligand–metal cooperativity in quinonoid based nickel(<scp>ii</scp>) and cobalt(<scp>ii</scp>) complexes for catalytic hydrosilylative reduction of nitriles to amines: electron transfer and mechanistic insight
  作者：Krishnendu Paramanik、Nilaj Bandopadhyay、Gayetri Sarkar、Souvik Chatterjee、Suvojit Roy、Subhra Jyoti Panda、Chandra Shekhar Purohit、Bhaskar Biswas、Hari Sankar Das

  DOI：10.1039/d3dt00090g

  日期：——

  realistically designed two complexes based on nickel(II) and cobalt(II) with a redox-active imino-o-benzoquinonato ligand. The compounds were characterized by a suite of spectroscopic methods, cyclic voltammetry and single-crystal X-ray diffraction. Both complexes showed excellent catalytic activity in transforming various organonitriles into the corresponding primary amines selectively using the inexpensive

  通过使用廉价的硅烷聚甲基氢硅氧烷 (PMHS) 催化还原腈来可持续生产特殊胺，有望取代适用性有限且涉及使用昂贵金属催化剂的传统合成路线。晚期 3d 金属配合物的使用为合理设计廉价催化剂提供了一个极好的平台，通过金属-配体协同作用精确控制其电子和结构特征。在这种情况下，我们实际设计了两种基于镍 ( II ) 和钴 ( II ) 的配合物，具有氧化还原活性的亚氨基-o-苯并醌配体。这些化合物通过一系列光谱方法、循环伏安法和单晶 X 射线衍射进行了表征。两种配合物在使用廉价的 PMHS 选择性地将各种有机腈转化为相应的伯胺方面表现出优异的催化活性。通过各种控制实验和光谱研究评估配合物的催化性能，并通过详细的计算计算揭示了非无辜的亚氨基-o-苯并醌配体和金属( II )离子协同性在控制关键反应活性和选择性方面的关键作用催化还原过程中的金属氢化物中间体。
• Catalytic fate of structurally characterized manganese(<scp>iii</scp>)–salen complexes towards efficient transformation of primary amides to amines or nitriles using hydrosilane
  作者：Nilaj Bandopadhyay、Krishnendu Paramanik、Gayetri Sarkar、Souvik Chatterjee、Suvojit Roy、Subhra Jyoti Panda、Chandra Shekhar Purohit、Bhaskar Biswas、Hari Sankar Das

  DOI：10.1039/d3nj01183f

  日期：——

  A convenient and selective hydrosilylative transformation of chemically inert primary amides (26 examples) into the corresponding primary amines with key functional group tolerance has been developed by using simple well-defined O,N,N,O donor salen-based earth abundant manganese(III) complexes under mild conditions. On a slight modification of the reaction condition by adding the blocking agent secondary

  通过使用简单的定义明确的 O、N、N、O 供体基于沙仑的地球丰富的锰 ( III) 复合物在温和条件下。通过添加封端剂仲酰胺稍微改变反应条件，伯酰胺向胺的转化在中间腈态停止（9 个例子）。同样的催化剂也有能力使用廉价的硅烷如聚甲基氢硅氧烷 (PMHS) 将腈还原为胺（15 个例子）。还进行了机理研究和 DFT 计算，以了解反应机理和化学选择性。在这种催化转化中，锰催化剂激活伯酰胺，整个还原过程通过伯酰胺脱水为相应的腈，然后还原为相应的伯胺。
• Synthesis of 2,6-disubstituted benzylamine derivatives as reversible selective inhibitors of copper amine oxidases
  作者：Francesco Lucchesini、Marco Pocci、Silvana Alfei、Vincenzo Bertini、Franca Buffoni

  DOI：10.1016/j.bmc.2014.01.037

  日期：2014.3

  In order to obtain substrate-like inhibitors of copper amine oxidases (CAOs), a class of enzymes involved in important cellular processes as well as in crosslinking of elastin and collagen and removal of biogenic primary amines, we synthesized a set of benzylamine derivatives properly substituted at positions 2 and 6 and studied their biological activity towards some members of CAOs.With benzylamines 6, 7, 8 containing linear alkoxy groups we obtained reversible inhibitors of benzylamine oxidase (BAO), very active and selective toward diamine oxidase (DAO), lysyl oxidase (LO) and monoamine oxidase B (MAO B) characterized by a certain toxicity consequent to the crossing of the brain barrier. Poorly toxic, up to very active, reversible inhibitors of BAO, very selective toward DAO, LO and MAO B, were obtained with benzylamines 10, 11, 12 containing hydrophilic x-hydroxyalkoxy groups. With benzylamines 13, 14, 15, containing linear alkyl groups endowed with steric, but not conjugative effects for the absence of properly positioned oxygen atoms, we synthesized moderately active inhibitors of BAO reversible and selective toward DAO, LO and MAO B.The cross examination of the entire biological data brought us to the conclusion that the bioactive synthesized compounds most likely exert their physiological role of reversible inhibitors in consequence of the formation of a plurality of hydrogen bonds or hydrophobic non-covalent interactions with proper sites in the protein. Accordingly, the reported inhibitors may be considered as a set of research tools for general biological studies and the formation of enzyme complexes useful for X-ray structure determinations aimed at the design of more sophisticated inhibitors to always better modulate the protein activity without important side effects. (C) 2014 Elsevier Ltd. All rights reserved.