trans-2-tert-butyl-1-(methoxycarbonyl)-3,5-dimethylimidazolidin-4-one | 132376-58-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-2-tert-butyl-1-(methoxycarbonyl)-3,5-dimethylimidazolidin-4-one
• 英文别名: methyl (2R,5R)-2-tert-butyl-3,5-dimethyl-4-oxoimidazolidine-1-carboxylate
• CAS: 132376-58-0；132376-59-1
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: OERGMBZMDFVYLI-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  49.85
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-2-tert-butyl-1-(methoxycarbonyl)-3,5-dimethylimidazolidin-4-one 在 正丁基锂 、 lithium diisopropyl amide 作用下， 生成 cis-2-tert-butyl-1-(methoxycarbonyl)-3,5-dimethylimidazolidin-4-one
  参考文献：
  名称：

  Pyramidalization and reactivity of trigonal centers. X-ray crystal structure analysis of two silyl enol ethers from 1-benzoyl- and 1-(methoxycarbonyl)-2-tert-butyl-3,5-dimethyl-4-imidazolidinone (reagents for amino acid synthesis)

  摘要：

  The title structures, which may be considered models for the Li enolates, contain three trigonal centers (N1, N3, C5) with unusually large pyramidalization. This leads to an all-trans arrangement of four substituents with respect to the plane of the five-membered ring which is in a flat twist conformation, bearing the tert-butyl group in a quasi-axial-type position. The pyramidalization on C5 is in the same direction from which this carbon undergoes electrophilic attack in reactions of the corresponding Li enolates.

  DOI：

  10.1021/ja00005a049
• 作为产物：
  描述：

  2-(tert-butyl)-3-methylimidazolidin-4-one 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 trans-2-tert-butyl-1-(methoxycarbonyl)-3,5-dimethylimidazolidin-4-one
  参考文献：
  名称：

  Pyramidalization and reactivity of trigonal centers. X-ray crystal structure analysis of two silyl enol ethers from 1-benzoyl- and 1-(methoxycarbonyl)-2-tert-butyl-3,5-dimethyl-4-imidazolidinone (reagents for amino acid synthesis)

  摘要：

  The title structures, which may be considered models for the Li enolates, contain three trigonal centers (N1, N3, C5) with unusually large pyramidalization. This leads to an all-trans arrangement of four substituents with respect to the plane of the five-membered ring which is in a flat twist conformation, bearing the tert-butyl group in a quasi-axial-type position. The pyramidalization on C5 is in the same direction from which this carbon undergoes electrophilic attack in reactions of the corresponding Li enolates.

  DOI：

  10.1021/ja00005a049

文献信息

• SEEBACH, DIETER;MAETZKE, THOMAS;PETTER, WALTER;KLOTZER, BERNHARD;PLATTNER+, J. AMER. CHEM. SOC., 113,(1991) N, C. 1781-1786
  作者：SEEBACH, DIETER、MAETZKE, THOMAS、PETTER, WALTER、KLOTZER, BERNHARD、PLATTNER+

  DOI：——

  日期：——