1,3-dibenzyl-4,5-dimethyl-1H-imidazol-2(3H)-one | 1167438-78-9

• 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-4,5-dimethyl-1H-imidazol-2(3H)-one
• 英文别名: 1,3-Dibenzyl-4,5-dimethylimidazol-2-one
• CAS: 1167438-78-9
• 化学式: C₁₉H₂₀N₂O
• 分子量: 292.381
• InChiKey: YNFXRUQRKXJOOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲基亚硝基脲 、 1,3-dibenzyl-4,5-dimethyl-1H-imidazol-2(3H)-one 在 potassium hydroxide 、 copper(l) chloride 作用下， 以 乙醚 、 水 、 二氯甲烷 为溶剂， 以36%的产率得到2,4-dibenzyl-1,5-dimethyl-2,4-diazabicyclo[3.1.0]hexan-3-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
• 作为产物：
  描述：

  3-羟基-2-丁酮 、 异氰酸苄酯 反应 1.5h， 以79%的产率得到N-(benzyl)-4,5-dimethyl-4-oxazolin-2-one
  参考文献：
  名称：

  4-恶唑啉-2-酮的一步合成及其在具有四元立体中心的多环结构构建中的应用

  摘要：

  报道了一种通过 α-酮醇和异氰酸酯的一锅 MW 促进缩合合成 4-恶唑啉-2-酮的新方法。还描述了使用相同起始材料的替代热方法。这些环状烯酰胺是有效的亲核试剂，可与迈克尔受体和异戊二烯基溴反应，得到各种带有一个或两个四元立体中心的多环结构。产物的选择性取决于反应条件和所用的亲电试剂。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900114

文献信息

• A Single-Step Synthesis of 4-Oxazolin-2-ones and Their Use in the Construction of Polycyclic Structures Bearing Quaternary Stereocenters
  作者：Blanca M. Santoyo、Carlos González-Romero、Omar Merino、Rafael Martínez-Palou、Aydeé Fuentes-Benites、Hugo A. Jiménez-Vázquez、Francisco Delgado、Joaquín Tamariz

  DOI：10.1002/ejoc.200900114

  日期：2009.5

  for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of α-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity

  报道了一种通过 α-酮醇和异氰酸酯的一锅 MW 促进缩合合成 4-恶唑啉-2-酮的新方法。还描述了使用相同起始材料的替代热方法。这些环状烯酰胺是有效的亲核试剂，可与迈克尔受体和异戊二烯基溴反应，得到各种带有一个或两个四元立体中心的多环结构。产物的选择性取决于反应条件和所用的亲电试剂。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Synthesis, Reactions, and Rearrangements of 2,4-Diazabicyclo[3.1.0]hexan-3-ones
  作者：Helmut Quast、Josef Walter Stawitz、Bodo Mueller

  DOI：10.3987/com-12-12543

  日期：——

  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.