3-氯-N-(1-苯乙基)苯甲酰胺 | 220306-62-7

• 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: 3-氯-N-(1-苯乙基)苯甲酰胺
• 英文名称: 3-chloro-N-(1-phenylethyl)benzamide
• CAS: 220306-62-7
• 化学式: C₁₅H₁₄ClNO
• 分子量: 259.735
• InChiKey: HHMRKSWBHLXSPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  α-苯乙胺 在 叔丁基过氧化氢 、 manganese(IV) oxide 、 N-氯代丁二酰亚胺 作用下， 以 水 、 乙腈 为溶剂， 反应 51.0h， 生成 3-氯-N-(1-苯乙基)苯甲酰胺
  参考文献：
  名称：

  MnO₂ Promoted Sequential C–O and C–N Bond Formation via C–H Activation of Methylarenes: A New Approach to Amides

  摘要：

  A novel and efficient approach for the synthesis of amides has been developed through manganese dioxide promoted nondirected C-H activation of methylarenes under mild reaction conditions employing N-chloroamines as effective coupling partners.

  DOI：

  10.1021/ol4023886

文献信息

• Iron/Caffeine as a Catalytic System for Microwave-Promoted Benzamide Formation
  作者：Xavier Bantreil、Pauline Navals、Jean Martinez、Frédéric Lamaty

  DOI：10.1002/ejoc.201403173

  日期：2015.1

  activation for this reaction. The benzamides were directly formed from alcohols and amine hydrochloride salts in short reaction times with yields up to 84 % and TOFs (turnover frequencies) up to 33.6 h–1. Among the examined transition metals, only nontoxic and inexpensive FeCl2·4H2O together with caffeine as a stabilizing ligand provided a uniquely efficient catalytic system for the transformation. Natural

  酰胺键是许多药物和聚合物中的基本单元。醇和胺的催化氧化是用有限的不需要的废物形成酰胺的有效方法。在此，我们展示了微波活化对该反应的有益效果。苯甲酰胺在很短的反应时间内由醇和胺盐酸盐直接形成，产率高达 84%，TOF（周转频率）高达 33.6 h–1。在所研究的过渡金属中，只有无毒且廉价的 FeCl2·4H2O 与作为稳定配体的咖啡因一起为转化提供了独特的高效催化体系。在酰胺化条件下也评估了咖啡因的天然来源。
• Anti-infective compounds
  申请人：Brodin Priscille

  公开号：US20110178077A1

  公开（公告）日：2011-07-21

  The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.

  本发明涉及小分子化合物及其在治疗细菌感染，特别是结核病方面的用途。
• Brønsted acid sites in the Beta zeolite induced highly efficient amidation of styrene in the aqueous phase
  作者：Jiteng Liu、Xueqin Jia、Lei Zhang、Wenqian Fu

  DOI：10.1039/d3nj05870k

  日期：——

  an environmentally friendly catalyst system is a highly attractive strategy for organic synthesis. In this work, a H-form mesoporous Beta (H-MBeta) zeolite with an irregular spherical particle shape was synthesized and was found to realize the direct amidation of styrene and nitriles for the synthesis of N-alkylated amides in the aqueous phase. This strong acidic H-MBeta catalyst exhibited superior activity

  开发环境友好的催化剂体系对于有机合成来说是一个极具吸引力的策略。本工作合成了一种具有不规则球形颗粒形状的H型介孔β（H-MBeta）沸石，并发现其可以实现苯乙烯和腈的直接酰胺化，从而在水相中合成N-烷基化酰胺。与酸脱铝法获得的H-MBeta-0.3和H-MBeta-1.0沸石相比，这种强酸性H-MBeta催化剂表现出优异的活性和产物选择性。这归因于H-MBeta沸石中存在丰富的强布朗斯台德酸位点，可以通过与质子氢相互作用的CC键诱导苯乙烯的吸附和活化，有利于关键中间碳正离子的形成。
• Iron‐Based Deep Eutectic Solvents: Key Players for Amide and Sulfonamide Synthesis and Alcohol Oxidation
  作者：Luciana Cicco、Sara Urselli、Claudia Favia、Filippo Maria Perna、Paola Vitale、Vito Capriati

  DOI：10.1002/ejoc.202400300

  日期：2024.6.24

  Selective and sustainable oxidation of secondary alcohols to their corresponding carbonyl compounds, alongside their applications as selective mono-alkylating reagents for both amide and arylsulfonamide derivatives, is achieved under aerobic and mild (40 °C) conditions in reusable Fe-based Lewis acidic deep eutectic solvents.

  在有氧和温和 (40°C) 条件下，在可重复使用的铁基路​​易斯酸性低共熔物中，实现了仲醇选择性和可持续氧化为其相应的羰基化合物，以及它们作为酰胺和芳基磺酰胺衍生物的选择性单烷基化试剂的应用溶剂。
• Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide
  作者：Xavier Bantreil、Nasreddine Kanfar、Nicolas Gehin、Ethan Golliard、Pauline Ohlmann、Jean Martinez、Frédéric Lamaty

  DOI：10.1016/j.tet.2014.06.001

  日期：2014.8

  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.