tert-butyl (2R,4R)-4-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-2-pentylpyrrolidine-1-carboxylate | 1184182-81-7

• 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 (2R,4R)-4-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-2-pentylpyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-2-pentylpyrrolidine-1-carboxylate
• CAS: 1184182-81-7
• 化学式: C₂₁H₄₃NO₄Si
• 分子量: 401.662
• InChiKey: VOHHJJNXVGIQLT-DYESRHJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以51%的产率得到tert-butyl (2S,4R)-4-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-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

• Alternative synthetic path to (−)-adalinine via a SmI2-promoted fragmentation of a 3-oxopyrrolidine derivative
  作者：Toshio Honda、Chihiro Hisa

  DOI：10.1016/j.tetlet.2009.05.114

  日期：2009.8

  A novel and stereocontrolled synthetic path to a coccinellid alkaloid. (-)-adalinine, was established by employing the reductive carbon-nitrogen bond cleavage reaction and subsequent recyclization of a 3-oxopyrrolidine derivative with samarium diiodide, as key steps, where water was found to be the best proton source. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.