N-p-methoxyphenyl-DL-3-phenyllactamide

• 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: N-p-methoxyphenyl-DL-3-phenyllactamide
• 英文别名: 2-hydroxy-N-(4-methoxyphenyl)-3-phenylpropanamide
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: WEMZMCSCUIJNRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-亚苄基-4-甲氧基苯胺 在 palladium on activated charcoal 甲酸铵 、 三乙胺 作用下， 以 乙二醇 为溶剂， 生成 N-p-methoxyphenyl-DL-3-phenyllactamide
  参考文献：
  名称：

  Microwave-Assisted Rapid and Simplified Hydrogenation^1,

  摘要：

  Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 degrees C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 degrees C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of beta-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters, Cleavage of the beta-lactam ring by hydrogenolysis of the N-C-4 bond of 4-aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.

  DOI：

  10.1021/jo981516s

文献信息

• Synthesis of α-Hydroxycarboxylic Acid Anilides via Copper-Catalyzed C–N Coupling of α-Hydroxyamides with Aryl Halides
  作者：Qingle Zeng、Zhijie Li、Quan Wen、Lihong Zhou、Xingmei Deng

  DOI：10.1055/s-0035-1560473

  日期：——

  α-hydroxycarboxylic acid anilides via copper-catalyzed chemoselective C–N coupling reactions of α-hydroxyamides and aryl halides is described. This highly selective N-arylation process demonstrates wide substrate scope, cost savings and easy operation. In addition, the chirality of l-3-phenyllactamide is preserved during the reaction. The synthesis of highly important α-hydroxycarboxylic acid anilides via copper-catalyzed

  摘要 描述了通过铜催化的α-羟基酰胺与芳基卤化物的化学选择性C-N偶联反应合成高度重要的α-羟基羧酸酐。这种高度选择性的N型芳构化工艺证明了广泛的基板范围，节省了成本并且易于操作。另外，手性升-3- phenyllactamide在反应过程中被保留。 描述了通过铜催化的α-羟基酰胺与芳基卤化物的化学选择性C-N偶联反应合成高度重要的α-羟基羧酸酐。这种高度选择性的N型芳构化工艺证明了广泛的基板范围，节省了成本并且易于操作。另外，手性升-3- phenyllactamide在反应过程中被保留。
• Microwave-Assisted Rapid and Simplified Hydrogenation¹^,
  作者：Bimal K. Banik、Khaled J. Barakat、Dilip R. Wagle、Maghar S. Manhas、Ajay K. Bose

  DOI：10.1021/jo981516s

  日期：1999.8.1

  Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 degrees C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 degrees C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of beta-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters, Cleavage of the beta-lactam ring by hydrogenolysis of the N-C-4 bond of 4-aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.