(3S,SR)-3-<(tert-butyldimethylsilyl)oxy>-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole | 146955-02-4

• 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: (3S,SR)-3-<(tert-butyldimethylsilyl)oxy>-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole
• 英文别名: (4S,SR)-4-(tert-butyldimethylsilyloxy)-3,4-dihydro-5-<(p-tolylsulfinyl)methyl>-2H-pyrrole；(3S,SR)-3-[(tert-butyldimethylsilyl)oxy]-4,5-dihydro-2-{[(4-methylphenyl)sulfinyl]methyl}-3H-pyrrole；tert-butyl-dimethyl-[[(4S)-5-[[(R)-(4-methylphenyl)sulfinyl]methyl]-3,4-dihydro-2H-pyrrol-4-yl]oxy]silane
• CAS: 146955-02-4
• 化学式: C₁₈H₂₉NO₂SSi
• 分子量: 351.585
• InChiKey: QPOIWTWKXDDDRW-HTAPYJJXSA-N

物化性质

• 沸点：
  437.5±45.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,SR)-3-<(tert-butyldimethylsilyl)oxy>-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 碘代三甲硅烷 、 四丁基氟化铵 、 三乙胺 作用下， 以 氘代氯仿 为溶剂， 反应 6.34h， 生成 流涎胺
  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：

  4-<(tert-butyldimethylsilyl)oxy>-3,4-dihydro-5-methyl-2H-pyrrole 、 (-)-menthyl p-toluenesulfinate 在 lithium diisopropyl amide 作用下， 生成 (3R,SR)-3-<(tert-butyldimethylsilyl)oxy>-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole 、 (3S,SR)-3-<(tert-butyldimethylsilyl)oxy>-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole
  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

• (1S,8S,8aS)-(+)-1-(tert-Butyldimethylsilyloxy)-8-hydroxy-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone
  作者：D. H. Hua、N. Lagneau、J. G. Park、L. A. Good、P. D. Robinson

  DOI：10.1107/s0108270195004963

  日期：1995.11.15

  The title compound C14H27NO3Si, obtained in good yield from a three-step sequence of reactions starting from (4S,SR)-4-(tert-butyldimethylsilyloxy)-3,4-dihydro-5- [(p-tolylsulfinyl)methyl]-2H-pyrrole, serves as a key intermediate in a study of the total synthesis of (+)-castanospermine. The six-membered lactam ring can be best described as having a distorted envelope conformation.
• 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.