ditert-butyl (4S,5S)-4,5-dimethylimidazolidine-1,3-dicarboxylate | 215882-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: ditert-butyl (4S,5S)-4,5-dimethylimidazolidine-1,3-dicarboxylate
• CAS: 215882-21-6
• 化学式: C₁₅H₂₈N₂O₄
• 分子量: 300.398
• InChiKey: NOKLOCTUHNQBMI-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ditert-butyl (4S,5S)-4,5-dimethylimidazolidine-1,3-dicarboxylate 在 仲丁基锂 作用下， 以 吡啶 为溶剂， 反应 48.5h， 生成 ditert-butyl (4R,5R)-2-[acetyloxy(phenyl)methyl]-4,5-dipropylimidazolidine-1,3-dicarboxylate
  参考文献：
  名称：

  Proton abstraction and electrophilic quench at C-2 of imidazolidines

  摘要：

  Imidazolidines bearing tert-butoxycarbonyl groups on both nitrogen atoms have been prepared in order to test their ability to act as acyl anion equivalents. Proton abstraction was achieved successfully at C-2, between the two nitrogen atoms, using the base sec-butyllithium. The resulting organolithium was trapped with a variety of electrophiles. The imidazolidine can be cleaved with acid to generate the desired carbonyl compound. Using chiral imidazolidines and aldehyde electrophiles, the carbon-carbon bond formation occurred with low diastereoselectivities. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00877-1
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 trans-4,5-Dimethylimidazolidine 以 氯仿 为溶剂， 反应 17.0h， 生成 ditert-butyl (4S,5S)-4,5-dimethylimidazolidine-1,3-dicarboxylate
  参考文献：
  名称：

  N,N′-Bisacylimidazolidines from 1,2-Diamines

  摘要：

  DOI：

  10.1055/s-1998-2176

文献信息

• N,N′-Bisacylimidazolidines from 1,2-Diamines
  作者：Iain Coldham、Philippe M. A. Houdayer、Robert A. Judkins、David R. Witty

  DOI：10.1055/s-1998-2176

  日期：1998.10
• Proton abstraction and electrophilic quench at C-2 of imidazolidines
  作者：Iain Coldham、Robert A. Judkins、David R. Witty

  DOI：10.1016/s0040-4020(98)00877-1

  日期：1998.11

  Imidazolidines bearing tert-butoxycarbonyl groups on both nitrogen atoms have been prepared in order to test their ability to act as acyl anion equivalents. Proton abstraction was achieved successfully at C-2, between the two nitrogen atoms, using the base sec-butyllithium. The resulting organolithium was trapped with a variety of electrophiles. The imidazolidine can be cleaved with acid to generate the desired carbonyl compound. Using chiral imidazolidines and aldehyde electrophiles, the carbon-carbon bond formation occurred with low diastereoselectivities. (C) 1998 Elsevier Science Ltd. All rights reserved.