(1S,6R,8aS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone | 146955-01-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,6R,8aS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone
• 英文别名: (1S,6R,8aS)-6-[(tert-butoxycarbonyl)amino]-1-[(tert-butyldimethylsilyl)oxy]-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone；tert-butyl N-[(1S,6R,8aS)-1-[tert-butyl(dimethyl)silyl]oxy-5-oxo-2,3,6,7,8,8a-hexahydro-1H-indolizin-6-yl]carbamate
• CAS: 146955-01-3
• 化学式: C₁₉H₃₆N₂O₄Si
• 分子量: 384.591
• InChiKey: JKXONINNQVGXEG-ILXRZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,6R,8aS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone 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：

  2-叔丁氧羰基氨基丙烯酸甲酯 在 镍 正丁基锂 、 氢气 作用下， 以 乙醇 为溶剂， -78.0~50.0 ℃ 、344.73 kPa 条件下， 反应 6.17h， 生成 (1S,6R,8aS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone
  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.