4-氯-N-(2-羟乙基)苯甲酰胺 | 7400-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-N-(2-羟乙基)苯甲酰胺
• 英文名称: 4-chloro-N-(2-hydroxyethyl)benzamide
• 英文别名: N-(p-chlorobenzoyl)-glycinol
• CAS: 7400-54-6
• 化学式: C₉H₁₀ClNO₂
• mdl: MFCD00461164
• 分子量: 199.637
• InChiKey: GBARCMIFTACERW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯-N-(2-羟乙基)苯甲酰胺 在 4-二甲氨基吡啶 、 甲基磺酰氯 、 三乙胺 、 sodium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 吗氯贝胺
  参考文献：
  名称：

  Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide

  摘要：

  A convenient and user-friendly method to yield benzamides from primary and secondary amines and various benzylic alcohols in the presence of a cheap iron salt (FeCl2 center dot 4H(2)O) and tert-butylhydroperoxide (70% in water) as a stoichiometric oxidant is described. Control experiments indicated that this reaction might involve radical species. This method proved to be general, generating a family of 30 benzamides and was applied to the preparative synthesis of anti-anxiety drug moclobemide. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.06.001
• 作为产物：
  描述：

  4-氯苯甲醇 在 叔丁基过氧化氢 、 sodium tetrahydroborate 、 iron(II) chloride tetrahydrate 、 calcium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 4.5h， 生成 4-氯-N-(2-羟乙基)苯甲酰胺
  参考文献：
  名称：

  Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide

  摘要：

  A convenient and user-friendly method to yield benzamides from primary and secondary amines and various benzylic alcohols in the presence of a cheap iron salt (FeCl2 center dot 4H(2)O) and tert-butylhydroperoxide (70% in water) as a stoichiometric oxidant is described. Control experiments indicated that this reaction might involve radical species. This method proved to be general, generating a family of 30 benzamides and was applied to the preparative synthesis of anti-anxiety drug moclobemide. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.06.001

文献信息

• Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters
  作者：Nikolaos F. Nikitas、Mary K. Apostolopoulou、Elpida Skolia、Anna Tsoukaki、Christoforos G. Kokotos

  DOI：10.1002/chem.202100655

  日期：2021.5.20

  the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a

  已经开发了用于芳族醛活化的便宜，容易且无金属的光化学方案。利用噻吨酮-9-one作为光催化剂，使用廉价的家用灯作为光源，已活化了多种芳香醛，然后通过一锅法将其转化为酰胺，异羟肟酸和酯，产率高至高。该方法的适用性在抗抑郁和社交焦虑药物莫氯贝胺的合成中得到了强调。为了确定该反应的合理机制，已经进行了详细的机理研究。
• A Mild and Regioselective Route to Functionalized Quinazolines
  作者：Tracy M. M. Maiden、Stephen Swanson、Panayiotis A. Procopiou、Joseph P. A. Harrity

  DOI：10.1002/chem.201502891

  日期：2015.10.5

  A Rh‐catalyzed ortho‐amidation cyclocondensation sequence gave a range of 4‐aminoquinazolines in high yield. The method features a remarkably mild C(sp2)H activation step and can be exploited to rapidly access compounds with established biological activity.

  Rh催化的邻酰胺化环缩合序列可高产率地得到一系列的4-氨基喹唑啉。该方法具有非常温和的C（sp 2）H活化步骤，可用于快速访问具有确定生物学活性的化合物。
• [EN] NOVEL METHODS FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] NOUVELLES MÉTHODES DE TRAITEMENT DES MALADIES INFLAMMATOIRES
  申请人：CORTICAL PTY LTD

  公开号：WO2004089927A1

  公开（公告）日：2004-10-21

  Methods of inhibiting the cytokine or biological activity of Macrophage Migration Inhibitory Factor (MIF) comprising contacting MIF with a compound of formula (I) are provided. The invention also relates to methods of treating diseases or conditions where MIF cytokine or biological activity is implicated comprising administration of compounds of formula (I), either alone or as a part of combination therapy. Novel compounds of formula (I) are also provided for.

  提供了抑制巨噬细胞迁移抑制因子（MIF）细胞因子或生物活性的方法，包括将MIF与式（I）化合物接触。该发明还涉及治疗MIF细胞因子或生物活性参与的疾病或病况的方法，包括给予式（I）化合物的治疗，可以单独使用或作为联合疗法的一部分。还提供了式（I）的新化合物。
• Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4<i>H</i>-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines
  作者：María C. Mollo、Liliana R. Orelli

  DOI：10.1021/acs.orglett.6b03122

  日期：2016.12.2

  general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported

  提出了通过微波辅助多磷酸（PPA）酯促进的ω-氨基醇的环化反应合成5至7元环亚氨基醚的第一个通用程序。使用聚磷酸乙酯/ CHCl 3有效地制备了2-芳基-2-恶唑啉和5,6-二氢-4 H -1,3-恶嗪。在无溶剂条件下，多磷酸三甲基甲硅烷基酯可合成迄今未报道的4,5,6,7-四氢-1,3-氧杂氮杂pine。该方法具有良好的收率和优异的收率，并且反应时间短。在手性底物中研究了PPA酯的反应机理和作用。
• Design, synthesis and biological evaluation of lazabemide derivatives as inhibitors of monoamine oxidase
  作者：Shiyang Zhou、Guangying Chen、Gangliang Huang

  DOI：10.1016/j.bmc.2018.08.024

  日期：2018.9

  In the studied a series novel of lazabemide derivatives were designed, synthesized and evaluated as inhibitors of monoamine oxidase (MAO-A or MAO-B). These compounds used lazabemide as the lead compound, and the chemistry structures were modified by used the bioisostere and modification of compound with alkyl principle. The two types of inhibitors (inhibition of MAO-A and inhibition of MAO-B) were

  在研究中，设计，合成和评估了一系列新的lazabemide衍生物作为单胺氧化酶（MAO-A或MAO-B）的抑制剂。这些化合物以拉沙贝米为先导化合物，并通过对烷基进行化合物的生物等排和修饰，对化学结构进行了修饰。通过对MAO的抑制活性来筛选两种抑制剂（对MAO-A的抑制和对MAO-B的抑制）。体外实验表明，化合物3a，3d和3f具有抑制MAO-A生物学活性的强度，而化合物3i和3m具有强度抑制MAO-B的生物学活性。从体外抑制活性实验的数据可以看出，化合物3d为IC 50  ＝ 3.12±0.05μmol/ mL的MAO-A，化合物3m为IC 50  ＝ 5.04±0.06μmol/ mL。通过检测血浆和脑组织中5-HT，NE，DA的含量以及MAO-A和MAO-B的活性，进行体内抑制活性实验以评估化合物3a，3d，3f，3i和3m的抑制活性。。体内抑制活性评估结果表明，化合物3a，3d，3f