(2S,3R,SR)-3-<(tert-butyldimethylsilyl)oxy>-2-<<(4-methylphenyl)sulfinyl>methyl>pyrrolidine | 146955-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,SR)-3-<(tert-butyldimethylsilyl)oxy>-2-<<(4-methylphenyl)sulfinyl>methyl>pyrrolidine
• 英文别名: tert-butyl-dimethyl-[(2S,3R)-2-[[(R)-(4-methylphenyl)sulfinyl]methyl]pyrrolidin-3-yl]oxysilane
• CAS: 146955-11-5
• 化学式: C₁₈H₃₁NO₂SSi
• 分子量: 353.601
• InChiKey: VNVXDENBNWUEEM-DRSNIGMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,SR)-3-<(tert-butyldimethylsilyl)oxy>-2-<<(4-methylphenyl)sulfinyl>methyl>pyrrolidine 在 镍 氢气 作用下， 以 乙醇 为溶剂， 22.0 ℃ 、101.32 kPa 条件下， 反应 12.0h， 以64%的产率得到(2R,3R)-3-<(tert-butyldimethylsilyl)oxy>-2-methylpyrrolidine
  参考文献：
  名称：

  Conjugate-addition reactions of .alpha.-sulfinyl ketimine anions with a methyl .alpha.-amidoacrylate. Concise asymmetric total syntheses of (-)-slaframine and (-)-6-epislaframine

  摘要：

  The in-situ 1,4-addition/ring-closure reactions of chiral alpha-sulfinyl ketimine anions with a methyl alpha-amidoacrylate provide a simple method for the construction of optically pure 6-aminoindolizidinones. This method afforded the syntheses of (-)-slaframine and (-)-6-epislaframine in six steps, respectively, from (+/-)-3-[(tert-butyldimethylsilyl)oxy]-4,5-dihydro-2-methyl-3H-pyrrole (9). Stereoselective reductions of alpha-sulfinyl ketimines (such as 10) were also developed.

  DOI：

  10.1021/jo00060a034
• 作为产物：
  描述：

  (-)-menthyl p-toluenesulfinate 在 Zn(BH3CN)2 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 (2S,3R,SR)-3-<(tert-butyldimethylsilyl)oxy>-2-<<(4-methylphenyl)sulfinyl>methyl>pyrrolidine
  参考文献：
  名称：

  Conjugate-addition reactions of .alpha.-sulfinyl ketimine anions with a methyl .alpha.-amidoacrylate. Concise asymmetric total syntheses of (-)-slaframine and (-)-6-epislaframine

  摘要：

  The in-situ 1,4-addition/ring-closure reactions of chiral alpha-sulfinyl ketimine anions with a methyl alpha-amidoacrylate provide a simple method for the construction of optically pure 6-aminoindolizidinones. This method afforded the syntheses of (-)-slaframine and (-)-6-epislaframine in six steps, respectively, from (+/-)-3-[(tert-butyldimethylsilyl)oxy]-4,5-dihydro-2-methyl-3H-pyrrole (9). Stereoselective reductions of alpha-sulfinyl ketimines (such as 10) were also developed.

  DOI：

  10.1021/jo00060a034