(2R,3R,2'S)-3-<(tert-butyldimethylsilyl)oxy>-2-<<(4-methylphenyl)sulfenyl>methyl>-1-pyrrolidine

• 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: (2R,3R,2'S)-3-<(tert-butyldimethylsilyl)oxy>-2-<<(4-methylphenyl)sulfenyl>methyl>-1-pyrrolidine
• 英文别名: (2S)-1-[(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(4-methylphenyl)sulfanylmethyl]pyrrolidin-1-yl]-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-one
• 化学式: C₂₈H₃₈F₃NO₃SSi
• 分子量: 553.761
• InChiKey: BIDZOHDDXHTFPH-XFAFFCHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (-)-menthyl p-toluenesulfinate 在 Zn(BH3CN)2 、 lithium diisopropyl amide 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 14.0h， 生成 (2R,3R,2'S)-3-<(tert-butyldimethylsilyl)oxy>-2-<<(4-methylphenyl)sulfenyl>methyl>-1-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

文献信息

• Conjugate-addition reactions of .alpha.-sulfinyl ketimine anions with a methyl .alpha.-amidoacrylate. Concise asymmetric total syntheses of (-)-slaframine and (-)-6-epislaframine
  作者：Duy H. Hua、Jewn Giew Park、Takeshi Katsuhira、S. Narasimha Bharathi

  DOI：10.1021/jo00060a034

  日期：1993.4

  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.