1,3-dibenzyl-4-methyl-1H-imidazol-2(3H)-one | 21035-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-dibenzyl-4-methyl-1H-imidazol-2(3H)-one
• 英文别名: 1,3-dibenzyl-4-methyl-1,3-dihydroimidazol-2-one；1,3-Dibenzyl-4-methyl-4-imidazolin-2-on；1,3-Dibenzyl-4-methylimidazol-2-one
• CAS: 21035-78-9
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: MBOXPLBDHGLGKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4-dibenzyl-2,4-diazabicyclo[3.1.0]hexan-3-one 在 硫酸 作用下， 以 水 为溶剂， 反应 1.0h， 以85%的产率得到1,3-dibenzyl-4-methyl-1H-imidazol-2(3H)-one
  参考文献：
  名称：

  2,4-二氮杂双环[3.1.0]hexan-3-ones的合成、反应和重排

  摘要：

  Copper-mediated cyclopropanation of 1,3-dialkyl-1,3-dihydroimidazol-2-ones with diazomethane and methyl diazoacetate yields 2,4-diazabicyclo[3.1.0]hexan-3-ones and the first diaza[4.3.1]propellane. The bicyclic system survives elevated temperatures and in strongly basic and acidic solutions, but drastic conditions cleave the (C-1) (C-6) bond affording 1,3-dihydroimidazol-2-ones. Catalytic hydrogenation removes N-benzyl groups and opens the (C-1) (C-6) bond. Lithium aluminium hydride reduces 2,4-dibenzyl-2,4-diazabicyclo[3.1.0]hexan-3-one to a bicyclic aminal. Acid-induced cleavage of its imidazolidine ring is followed by unexpected transformations that probably procede via an acyclic intermediate, which comprises an azomethine ylide and an iminium moiety. 1,3-Cyclization involving both functional groups leads to N,N'-dibenzyl-trans-1,2-cyclopropanediamine, while 1,5-cyclization gives rise to the formation of N-benzylpyrrole along with N-benzylamine.

  DOI：

  10.3987/com-12-12543

文献信息

• Schwartz reagent mediated synthesis of thiazolones and imidazolones from thiazolidine-2,4-diones and imidazolidine-2,4-diones
  作者：Srinivasa Reddy Dandepally、Radouane Elgoummadi、Alfred L. Williams

  DOI：10.1016/j.tetlet.2012.12.015

  日期：2013.2

  A novel reduction/elimination method of thiazolidine-2,4-dione and imidazolidine-2,4-dione derivatives using Schwartz reagent to synthesize numerous thiazolones and imidazolones in a single step is reported. (C) 2012 Elsevier Ltd. All rights reserved.