4-acetyl-5-methyl-1-phenyl-1,2-dihydroimidazol-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-acetyl-5-methyl-1-phenyl-1,2-dihydroimidazol-2-one
• 英文别名: 2H-Imidazol-2-one, 4-acetyl-1,3-dihydro-5-methyl-1-phenyl-；5-acetyl-4-methyl-3-phenyl-1H-imidazol-2-one
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: XEHIDPDKABNSRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2Z)-3-偶氮基-4-氧代-2-戊烯-2-醇 在 rhodium(II) octanoate 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 3.5h， 生成 4-acetyl-5-methyl-1-phenyl-1,2-dihydroimidazol-2-one
  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.