[2-oxo-2-phenyl-1-(3-phenylureido)ethyl]phosphonic acid diethyl ester | 819047-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-oxo-2-phenyl-1-(3-phenylureido)ethyl]phosphonic acid diethyl ester
• 英文别名: 1-(1-Diethoxyphosphoryl-2-oxo-2-phenylethyl)-3-phenylurea
• CAS: 819047-08-0
• 化学式: C₁₉H₂₃N₂O₅P
• 分子量: 390.376
• InChiKey: ZDCZJDYGDNKHRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-oxo-2-phenyl-1-(3-phenylureido)ethyl]phosphonic acid diethyl ester 在 potassium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (3-benzyl-2-oxo-1,5-diphenyl-2,3-dihydro-1H-imidazol-4-yl)phosphonic acid diethyl ester
  参考文献：
  名称：

  N−H Insertion Reactions of Primary Ureas:  The Synthesis of Highly Substituted Imidazolones and Imidazoles from Diazocarbonyls

  摘要：

  Primary ureas have been used as substrates in rhodium-catalyzed N-H insertion reactions with an array of diazocarbonyls. The insertion reaction is efficient and gives excellent selectivity and yields. The products from the insertion reaction with diazoketones cyclize readily in the presence of acid to yield the corresponding imidazolones that can be further derivatized by N-alkylation with alkyl, allyl, and benzyl halides. Alternatively, the imidazolones were treated with phosphorus oxybromide to form the corresponding 2-bromoimidazoles that were further functionalized using a Suzuki coupling reaction.

  DOI：

  10.1021/jo048353u
• 作为产物：
  描述：

  苯基脲 、 diethyl (1-diazo-2-oxo-2-phenylethyl)phosphonate 在 rhodium(II) octanoate 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 0.5h， 以88%的产率得到[2-oxo-2-phenyl-1-(3-phenylureido)ethyl]phosphonic acid diethyl ester
  参考文献：
  名称：

  N−H Insertion Reactions of Primary Ureas:  The Synthesis of Highly Substituted Imidazolones and Imidazoles from Diazocarbonyls

  摘要：

  Primary ureas have been used as substrates in rhodium-catalyzed N-H insertion reactions with an array of diazocarbonyls. The insertion reaction is efficient and gives excellent selectivity and yields. The products from the insertion reaction with diazoketones cyclize readily in the presence of acid to yield the corresponding imidazolones that can be further derivatized by N-alkylation with alkyl, allyl, and benzyl halides. Alternatively, the imidazolones were treated with phosphorus oxybromide to form the corresponding 2-bromoimidazoles that were further functionalized using a Suzuki coupling reaction.

  DOI：

  10.1021/jo048353u

文献信息

• N−H Insertion Reactions of Primary Ureas:  The Synthesis of Highly Substituted Imidazolones and Imidazoles from Diazocarbonyls
  作者：Sang-Hyeup Lee、Kazuhiro Yoshida、Hana Matsushita、Bruce Clapham、Guido Koch、Jürg Zimmermann、Kim D. Janda

  DOI：10.1021/jo048353u

  日期：2004.12.1

  Primary ureas have been used as substrates in rhodium-catalyzed N-H insertion reactions with an array of diazocarbonyls. The insertion reaction is efficient and gives excellent selectivity and yields. The products from the insertion reaction with diazoketones cyclize readily in the presence of acid to yield the corresponding imidazolones that can be further derivatized by N-alkylation with alkyl, allyl, and benzyl halides. Alternatively, the imidazolones were treated with phosphorus oxybromide to form the corresponding 2-bromoimidazoles that were further functionalized using a Suzuki coupling reaction.