2-phenoxy-N-phenylacetamide | 18705-01-6

• 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-phenoxy-N-phenylacetamide
• 英文别名: N-phenylphenoxyacetamide；phenoxyacetanilide
• CAS: 18705-01-6
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: VDLGLFVMQUNFST-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  444.2±28.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-phenoxy-N-phenylacetamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以14%的产率得到二苯胺
  参考文献：
  名称：

  A Convenient Preparation of N-Alkyl and N-Arylamines by Smiles Rearrangement—Synthesis of Analogues of Diclofenac

  摘要：

  Smiles rearrangement of substituted aryloxyacetamides in which oxygen and-nitrogen are separated by COCH2 group has been successful even when the aryloxy ring carries weak or no electron withdrawing group. Earlier reports of such reactions involved either strong electron withdrawing groups or a special catalyst. The diphenylamines thus obtained gave analogues of diclofenac in only one case.

  DOI：

  10.1081/scc-120021996
• 作为产物：
  描述：

  苯氧乙酸 在 morpholinomethyl polystyrene HL 、 PS-Ph₃P resin 、 三氯乙腈 作用下， 以 二氯甲烷 为溶剂， 生成 2-phenoxy-N-phenylacetamide
  参考文献：
  名称：

  EFFICIENT PROCEDURE FOR THE PREPARATION OF AMIDES USING POLYMER-BOUND REAGENTS

  摘要：

  An effective method for the conversion of acids into amides is presented. The two-step procedure includes the preparation of acid chloride intermediates using Pol-Ph3P and subsequent treatment of these intermediates with amines and polymer-bound base. The amides were accessible in high yields and purities without further purification.

  DOI：

  10.1081/scc-100103528

文献信息

• Copper-catalyzed transformation of alkyl nitriles to <i>N</i>-arylacetamide using diaryliodonium salts
  作者：Romain Sallio、Pierre-Adrien Payard、Paweł Pakulski、Iryna Diachenko、Indira Fabre、Sabine Berteina-Raboin、Cyril Colas、Ilaria Ciofini、Laurence Grimaud、Isabelle Gillaizeau

  DOI：10.1039/d1ra02305e

  日期：——

  This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.

  这项工作报告了一种简单有效的方法，用于使用环保的二芳基碘鎓盐对烷基腈进行铜催化的氧化还原中性转化并生成N-芳基乙酰胺。该方法效率高、底物范围广、官能团耐受性好。
• Water-Soluble Acylating Agents: Preparation of 2-Acylthio-1-alkylpyridinium Salts and Acylation of Phenols, Acids, and/or Amines with These Salts in an Aqueous Phase
  作者：Tohru Sakakibara、Yukie Watabe、Masahide Yamada、Rokuro Sudoh

  DOI：10.1246/bcsj.61.247

  日期：1988.1

  Reaction of phenols, amines, and acids with 2-benzoylthio-1-methylpyridinium chloride prepared in situ from benzoyl chloride and 1-methyl-2(1H)-pyridinethione, afforded the corresponding benzoyl derivatives in good yields. In the reaction of p-nitrophenol, even a catalytic amount of 1-methyl-2(1H)-pyridinethione proved to be effective. Similar reactions of p-nitrophenol with isobutyryl chloride and acetyl

  苯甲酰氯和 1-甲基-2(1H)-吡啶硫酮原位制备的 2-苯甲酰硫基-1-甲基氯化吡啶鎓与苯酚、胺和酸反应，以良好的收率得到相应的苯甲酰衍生物。在对硝基苯酚的反应中，即使是催化量的 1-甲基-2(1H)-吡啶硫酮也被证明是有效的。在 1-甲基-2(1H)-吡啶硫酮存在下，对硝基苯酚与异丁酰氯和乙酰氯的类似反应分别以 63% 和 44% 的产率得到对硝基苯异丁酸酯和对硝基苯乙酸酯。2-苯甲酰硫基-、2-乙酰硫基-和2-异丁酰硫基-1-乙基吡啶鎓四氟硼酸盐通过用四氟硼酸三乙基氧鎓处理相应的2-酰基硫代吡啶鎓来制备。这些吡啶鎓盐还在水相中充当酰化剂。
• Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively
  作者：Hidefumi Nakatsuji、Mami Morimoto、Tomonori Misaki、Yoo Tanabe

  DOI：10.1016/j.tet.2007.08.117

  日期：2007.11

  practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an

  我们开发了两种有效的实用方法，分别用于酰氯与醇，胺，硫醇之间的酯化，酰胺形成和硫酯化。本发明的温和而稳固的反应是通过两种单独的方法进行的，两者都是通过组合廉价且容易获得的胺，N-甲基咪唑和N，N，N '，N'-四甲基乙二胺（TMEDA）。方法A使用等摩尔量的K 2 CO 3催化N-甲基咪唑和TMEDA ，而方法B使用等摩尔量的N-甲基咪唑和TMEDA。其主要特征如下。（i）就反应性而言，方法B在酯化和硫代酯化方面优于方法A，而经济高效的方法A在酰胺形成方面优于方法B。（ii）酰氯与较少亲核和立体拥挤的胺（如2,6-二氯苯胺）之间的酰胺形成过程顺利进行。（iii）该方案适用于成功合成两种农用化学品，溴丁酸酯和杀虫剂。
• An Environmentally Benign, Catalyst‐Free N−C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides
  作者：Vishal Kumar、Sanjeev Dhawan、Pankaj Sanjay Girase、Parvesh Singh、Rajshekhar Karpoormath

  DOI：10.1002/ejoc.202101114

  日期：2021.11.8

  An unprecedented methodology for the synthesis of a variety of organic amides through the coupling of wide range of unactivated primary, secondary, and tertiary diversified amides, with different amines is reported. The acid-promoted reaction is proposed to proceed through carbonyl activation and is accompanied by broad substrate scope with high tolerance for functional groups.

  报道了一种通过将各种未活化的伯、仲和叔多样化酰胺与不同胺偶联来合成各种有机酰胺的前所未有的方法。酸促进反应被提议通过羰基活化进行，并且伴随着广泛的底物范围和对官能团的高耐受性。
• The catalytic activity of titania nanostructures in the synthesis of amides under solvent-free conditions
  作者：Sangaraiah Nagarajan、Park Ran、Poovan Shanmugavelan、Murugan Sathishkumar、Alagusundaram Ponnuswamy、Kee Suk Nahm、G. Gnana kumar

  DOI：10.1039/c2nj40119c

  日期：——

  Different shapes and phases of titania nanostructures with the uniform size distribution were synthesized by hydrothermal sol–gel technique. The influence of annealing temperature on the crystalline character, size and phase of the prepared nanomaterials were evidenced from the diffraction analysis. Infrared spectroscopic analysis ensured the structural confirmation of the sulfated titania nanostructures. Catalytic activity of the synthesized nanometric materials in direct amidation of aromatic and aliphatic carboxylic acids with aromatic amines was evaluated. Among the materials studied, sulfated titania nanotubes with the anatase phase exhibited excellent catalytic activity. The employed solvent-free protocol is greener and eradicates the drawbacks associated with the hazardous solvents employed in the prevailing solution phase methodologies.

  利用水热溶胶-凝胶技术合成了具有均匀尺寸分布的不同形状和相态的二氧化钛纳米结构。通过衍射分析证实了退火温度对制备的纳米材料的晶体特性、尺寸和相态的影响。红外光谱分析确保了硫酸化二氧化钛纳米结构的结构确认。评估了合成的纳米级材料在芳香和脂肪族羧酸与芳香胺直接酰胺化反应中的催化活性。在研究的材料中，具有锐钛矿相的硫酸化二氧化钛纳米管表现出优异的催化活性。所采用的无溶剂方案更环保，并克服了当前溶液相方法中使用的危险溶剂的缺点。