tert-butyl (2S,4R)-4-tert-butyldimethylsilyloxy-2-{[(1Z)-4-tert-butyldimethylsilyloxy]but-1-en-1-yl}-2-pentylpyrrolidine-1-carboxylate | 1184182-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,4R)-4-tert-butyldimethylsilyloxy-2-{[(1Z)-4-tert-butyldimethylsilyloxy]but-1-en-1-yl}-2-pentylpyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(Z)-4-[tert-butyl(dimethyl)silyl]oxybut-1-enyl]-2-pentylpyrrolidine-1-carboxylate
• CAS: 1184182-82-8
• 化学式: C₃₀H₆₁NO₄Si₂
• 分子量: 555.99
• InChiKey: OHPYZMPBHCISJO-QXAVBPBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4R)-4-tert-butyldimethylsilyloxy-2-{[(1Z)-4-tert-butyldimethylsilyloxy]but-1-en-1-yl}-2-pentylpyrrolidine-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到tert-butyl (2S,4R)-4-hydroxy-2-[(1Z)-4-hydroxybut-1-en-1-yl]-2-pentylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Application of Samarium Diiodide-Promoted Reductive Carbon-Nitrogen Bond Cleavage Reaction to 3-Oxopyrrolidine Derivatives: Alternative Synthesis of a Coccinellid Alkaloid, (-)-Adalinine

  摘要：

  Samarium diiodide-promoted reductive deamination reaction was applied to 5,5-disubstitued 3-oxopyrrolidines to provide 4,4-disubstituted 4-aminobutan-2-one derivatives, where the carbon-nitrogen bond cleavage took place at the desired position, regioselectively. This strategy was exploited in the synthesis of a coccinellid alkaloid, (-)-adalinine.

  DOI：

  10.3987/com-09-s(s)130
• 作为产物：
  描述：

  (2S,4R)-1-tert-butoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-pentyl-2-pyrrolidinecarboxaldehyde 、 [3-[(tert-butyldimethylsilyl)oxy]propyl]triphenylphosphonium bromide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以87%的产率得到tert-butyl (2S,4R)-4-tert-butyldimethylsilyloxy-2-{[(1Z)-4-tert-butyldimethylsilyloxy]but-1-en-1-yl}-2-pentylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Application of Samarium Diiodide-Promoted Reductive Carbon-Nitrogen Bond Cleavage Reaction to 3-Oxopyrrolidine Derivatives: Alternative Synthesis of a Coccinellid Alkaloid, (-)-Adalinine

  摘要：

  Samarium diiodide-promoted reductive deamination reaction was applied to 5,5-disubstitued 3-oxopyrrolidines to provide 4,4-disubstituted 4-aminobutan-2-one derivatives, where the carbon-nitrogen bond cleavage took place at the desired position, regioselectively. This strategy was exploited in the synthesis of a coccinellid alkaloid, (-)-adalinine.

  DOI：

  10.3987/com-09-s(s)130

文献信息

• Application of Samarium Diiodide-Promoted Reductive Carbon-Nitrogen Bond Cleavage Reaction to 3-Oxopyrrolidine Derivatives: Alternative Synthesis of a Coccinellid Alkaloid, (-)-Adalinine
  作者：Toshio Honda、Chihiro Hisa

  DOI：10.3987/com-09-s(s)130

  日期：——

  Samarium diiodide-promoted reductive deamination reaction was applied to 5,5-disubstitued 3-oxopyrrolidines to provide 4,4-disubstituted 4-aminobutan-2-one derivatives, where the carbon-nitrogen bond cleavage took place at the desired position, regioselectively. This strategy was exploited in the synthesis of a coccinellid alkaloid, (-)-adalinine.