[(3S)-3-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxybutyl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate | 144762-79-8

• 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: [(3S)-3-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxybutyl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS: 144762-79-8
• 化学式: C₂₀H₃₆N₂O₆
• 分子量: 400.516
• InChiKey: NCKZYFSOBNTTCN-AWEZNQCLSA-N

物化性质

• 沸点：
  468.3±45.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3S)-3-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxybutyl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 barium dihydroxide 、 甲烷磺酸 作用下， 生成 (S)-(+)-1,3-丁二醇
  参考文献：
  名称：

  Chiral α,ω-dioxy-carbanions from 1,3-propanediol and 1,4-butanediol by sparteine-assisted deprotonation. Enantioselective synthesis of 1,3- and 1,4-diols, (R)-pantolactone, and a cyclopropane.

  摘要：

  Prostereogenic mono- and dicarbamates of 1,3-propanediol and 1,4-butanediol are deprotonated by the sec-butyllithium/(-)-sparteine system with high enantiotopic differentiation. The electrophilic substitution of the intermediate chiral carbanions furnishes the title compounds with >95% ee.

  DOI：

  10.1016/s0040-4039(00)79083-6
• 作为产物：
  描述：

  2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride 在 仲丁基锂 、 鹰爪豆碱 作用下， 反应 16.0h， 生成 [(3S)-3-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxybutyl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Chiral α,ω-dioxy-carbanions from 1,3-propanediol and 1,4-butanediol by sparteine-assisted deprotonation. Enantioselective synthesis of 1,3- and 1,4-diols, (R)-pantolactone, and a cyclopropane.

  摘要：

  Prostereogenic mono- and dicarbamates of 1,3-propanediol and 1,4-butanediol are deprotonated by the sec-butyllithium/(-)-sparteine system with high enantiotopic differentiation. The electrophilic substitution of the intermediate chiral carbanions furnishes the title compounds with >95% ee.

  DOI：

  10.1016/s0040-4039(00)79083-6

文献信息

• Stereoselective generation of 1,3- and 1,4-dioxy-substituted carbanions by sparteine-assisted deprotonation of chiral precursors: Substrate or reagent control in the synthesis of α,γ- and α,δ-diols
  作者：Hartmut Ahrens、Mario Paetow、Dieter Hoppe

  DOI：10.1016/s0040-4039(00)79084-8

  日期：1992.9

  The deprotonation of a dicarbamate, derived from (S)-butane-1,3-diol, by sec-butyllithium takes an highly diastereoselective, but opposite, direction in the presence of (-)-sparteine and of tetramethylethylenediamine (TMEDA), respectively. The (S)-pentane-1,4-diol derivative shows the same stereochemical preference under both conditions.
• Chiral α,ω-dioxy-carbanions from 1,3-propanediol and 1,4-butanediol by sparteine-assisted deprotonation. Enantioselective synthesis of 1,3- and 1,4-diols, (R)-pantolactone, and a cyclopropane.
  作者：Mario Paetow、Hartmut Ahrens、Dieter Hoppe

  DOI：10.1016/s0040-4039(00)79083-6

  日期：1992.9

  Prostereogenic mono- and dicarbamates of 1,3-propanediol and 1,4-butanediol are deprotonated by the sec-butyllithium/(-)-sparteine system with high enantiotopic differentiation. The electrophilic substitution of the intermediate chiral carbanions furnishes the title compounds with >95% ee.