4-(2-Bromophenyl)-3-phenoxy-1-prop-2-enylazetidin-2-one | 243455-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4-(2-Bromophenyl)-3-phenoxy-1-prop-2-enylazetidin-2-one
• 英文别名: 4-(2-bromophenyl)-3-phenoxy-1-prop-2-enylazetidin-2-one
• CAS: 243455-68-7
• 化学式: C₁₈H₁₆BrNO₂
• 分子量: 358.235
• InChiKey: MBEYCCISQWZPER-UHFFFAOYSA-N

物化性质

• 沸点：
  486.5±45.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-Bromophenyl)-3-phenoxy-1-prop-2-enylazetidin-2-one 在 palladium on activated charcoal 甲酸铵 作用下， 以 乙二醇 为溶剂， 生成 3-phenoxy-4-phenyl-1-propyl-azetidin-2-one 、 2-phenoxy-3-phenyl-N-propylpropanamide
  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
• 作为产物：
  描述：

  邻溴苯甲醛 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-(2-Bromophenyl)-3-phenoxy-1-prop-2-enylazetidin-2-one
  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

• Ng, Sze Sze; Banik, Indrani; Okawa, Atsushi, Journal of Chemical Research - Part S, 2001, # 3, p. 118 - 119
  作者：Ng, Sze Sze、Banik, Indrani、Okawa, Atsushi、Becker, Frederick F.、Banik, Bimal K.

  DOI：——

  日期：——
• 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.