(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-1-prop-2-enylpyrrolidine-2-carbonitrile | 213131-29-4

• 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: (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-1-prop-2-enylpyrrolidine-2-carbonitrile
• CAS: 213131-29-4
• 化学式: C₁₄H₂₆N₂OSi
• 分子量: 266.459
• InChiKey: MQPGXKZGCPCCBU-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-1-prop-2-enylpyrrolidine-2-carbonitrile 在 盐酸 、 Amberlyst 15 作用下， 以 甲醇 为溶剂， 生成 methyl (2S,3S)-3-hydroxy-1-prop-2-enylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Reductive cyanation: A key step for a short synthesis of (−)-(2S,3S)-3-hydroxyproline

  摘要：

  A short stereoselective synthesis of (-)-(2S,3S)-3-hydroxyproline has been realized from L-malic acid as the source of chirality. The key step was the reductive cyanation of the intermediate la, in high stereoselectivity and yield. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01133-2
• 作为产物：
  描述：

  (3S)-3-hydroxy-1-prop-2-enylpyrrolidin-2-one 在 咪唑 、 二异丁基氢化铝 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-1-prop-2-enylpyrrolidine-2-carbonitrile
  参考文献：
  名称：

  Reductive cyanation: A key step for a short synthesis of (−)-(2S,3S)-3-hydroxyproline

  摘要：

  A short stereoselective synthesis of (-)-(2S,3S)-3-hydroxyproline has been realized from L-malic acid as the source of chirality. The key step was the reductive cyanation of the intermediate la, in high stereoselectivity and yield. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01133-2

文献信息

• Reductive cyanation: A key step for a short synthesis of (−)-(2S,3S)-3-hydroxyproline
  作者：Jean-Olivier Durand、Marc Larchevêque、Yves Petit

  DOI：10.1016/s0040-4039(98)01133-2

  日期：1998.8

  A short stereoselective synthesis of (-)-(2S,3S)-3-hydroxyproline has been realized from L-malic acid as the source of chirality. The key step was the reductive cyanation of the intermediate la, in high stereoselectivity and yield. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.