N-((4-甲基苯甲酰基)氧基)苯甲酰胺 | 51860-35-6

• 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: N-((4-甲基苯甲酰基)氧基)苯甲酰胺
• 英文名称: N-((4-methylbenzoyl)oxy)benzamide
• 英文别名: N-(4-methylbenzoyloxy)benzamide；N-benzoyl-O-p-toluoyl-hydroxylamine；N-Benzoyl-O-p-toluoyl-hydroxylamin；O-p-Toluyl-N-benzoyl-hydroxylamin；Benzhydroxamsaeure-p-toluat；Benz-p-tolhydroxamsaeure
• CAS: 51860-35-6
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: IYHLMMYWPIAQKU-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-((4-甲基苯甲酰基)氧基)苯甲酰胺 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium pivalate 、 potassium hydroxide 、 三甲基乙酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 (E)-2-styrylbenzoic acid
  参考文献：
  名称：

  Rh(III)-Catalyzed Directed C−H Olefination Using an Oxidizing Directing Group: Mild, Efficient, and Versatile

  摘要：

  An efficient Rh(III)-catalyzed oxidative olefination by directed C-H bond activation of N-methoxybenzamides is reported. In this mild, practical, selective, and high-yielding process, the N-O bond acts as an internal oxidant. In addition, simply changing the substituent of the directing/oxidizing group results in the selective formation of valuable tetrahydroisoquinolinone products.

  DOI：

  10.1021/ja109676d
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 苯 作用下， 生成 N-((4-甲基苯甲酰基)氧基)苯甲酰胺
  参考文献：
  名称：

  Lossen, Justus Liebigs Annalen der Chemie, 1894, vol. 281, p. 225

  摘要：

  DOI：

文献信息

• Facile synthesis of <i>O</i>-acylhydroxamates <i>via</i> reaction of oxime chlorides with carboxylic acids
  作者：Kai-Kai Wang、Yan-Li Li、Ying-Chao Zhao、Shan-Shan Zhang、Rongxiang Chen、Aili Sun

  DOI：10.1039/d1ra06860a

  日期：——

  A simple and efficient method for the synthesis of O-acylhydroxamate derivatives from oxime chlorides and carboxylic acids was developed. The reaction affords clean and facile access to diverse O-acylhydroxamates in high yields (up to 85%). The chemical structure of a typical product was confirmed using single-crystal X-ray structure analysis.

  开发了一种从肟氯化物和羧酸合成 O-酰基异羟肟酸酯衍生物的简单有效的方法。该反应能够以高产率（高达 85%）清洁、简便地获得多种 O-酰基异羟肟酸酯。使用单晶 X 射线结构分析确认了典型产品的化学结构。
• Catalyst-Controlled Regioselective Synthesis of α-Amino Oxime Esters from <i>N</i> -(Acyloxy)amides and 2<i>H</i> -Azirines
  作者：Feifei Wu、Wanzhi Chen、Miaochang Liu、Huayue Wu

  DOI：10.1002/ejoc.201801195

  日期：2018.11.1

  Palladium‐ and rhodium‐catalyzed selective reactions of 2H‐azirines and N‐(acyloxy)amides leading to α‐amino oxime esters were described. The regioselectivity is catalyst‐controlled, and two different α‐amino oxime esters were chemoselectively obtained in high yields.

  描述了钯和铑催化的2 H-叠氮基和N-（酰氧基）酰胺生成α-氨基肟酯的选择性反应。区域选择性是由催化剂控制的，并且以高收率通过化学选择获得了两种不同的α-氨基肟酯。
• <i>N</i>-Amidation by Copper-Mediated Cross-Coupling of Organostannanes or Boronic Acids with <i>O</i>-Acetyl Hydroxamic Acids
  作者：Zhihui Zhang、Ying Yu、Lanny S. Liebeskind

  DOI：10.1021/ol8009682

  日期：2008.7.17

  A general nonoxidative N-amidation of organostannanes and boronic acids has been developed. Under nonbasic conditions a wide variety of aryl, alkenyl, and heteroaryl organostannanes and boronic acids couple efficiently with O-acetyl hydroxamic acids in the presence of Cu(I) sources.