(1S,6S,8aS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7,8,8a-octahydroindolizine | 146955-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1S,6S,8aS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7,8,8a-octahydroindolizine
• 英文别名: (1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-[(tert-butyldimethylsilyl)oxy]-1,2,3,5,6,7,8,8a-octahydroindolizine；tert-butyl N-[(1S,6S,8aS)-1-[tert-butyl(dimethyl)silyl]oxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl]carbamate
• CAS: 146955-17-1
• 化学式: C₁₉H₃₈N₂O₃Si
• 分子量: 370.608
• InChiKey: YYEIYPJBKSNTNZ-JYJNAYRXSA-N

物化性质

• 沸点：
  419.8±45.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,6S,8aS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7,8,8a-octahydroindolizine 在 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 1.25h， 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 sodium hydroxide 、 硼烷四氢呋喃络合物 作用下， 反应 5.08h， 生成 (1S,6S,8aS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7,8,8a-octahydroindolizine
  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.