(S)-(+)-(N-(S)-p-toluenesulfinyl)-2-amino-5,5-(ethylenedioxy)-heptanonitrile | 332072-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(+)-(N-(S)-p-toluenesulfinyl)-2-amino-5,5-(ethylenedioxy)-heptanonitrile
• 英文别名: (S)-N-[(1S)-1-cyano-4-(2-methyl-1,3-dioxolan-2-yl)butyl]-4-methylbenzenesulfinamide
• CAS: 332072-78-3
• 化学式: C₁₆H₂₂N₂O₃S
• 分子量: 322.428
• InChiKey: XLYFTZFTOPMEAG-FPTDNZKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  90.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-(+)-(N-(S)-p-toluenesulfinyl)-2-amino-5,5-(ethylenedioxy)-heptanonitrile 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 生成 (2S,6S)-6-methyl-2-piperidinecarboxylic acid hydrochloride
  参考文献：
  名称：

  Masked Oxo Sulfinimines (N-Sulfinyl Imines) in the Asymmetric Synthesis of Proline and Pipecolic Acid Derivatives

  摘要：

  [GRAPHICS]On addition of Et2AlCN/i-PrOH, masked oxo sulfinimines give alpha -amino nitriles that afford oxo alpha -amino acids on hydrolysis. These amino acids cyclize and are reduced to cis proline and cis pipecolic acids derivatives in high ee and good yield. This new procedure avoids many of the limitations related to the preparation of oxo amino acids from proteinogenic amino acids.

  DOI：

  10.1021/ol015520t
• 作为产物：
  描述：

  4-(2-甲基-1,3-二氧杂烷-2-基)丁酸乙酯 在 二异丁基氢化铝 、 异丙醇 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-(+)-(N-(S)-p-toluenesulfinyl)-2-amino-5,5-(ethylenedioxy)-heptanonitrile
  参考文献：
  名称：

  Masked Oxo Sulfinimines (N-Sulfinyl Imines) in the Asymmetric Synthesis of Proline and Pipecolic Acid Derivatives

  摘要：

  [GRAPHICS]On addition of Et2AlCN/i-PrOH, masked oxo sulfinimines give alpha -amino nitriles that afford oxo alpha -amino acids on hydrolysis. These amino acids cyclize and are reduced to cis proline and cis pipecolic acids derivatives in high ee and good yield. This new procedure avoids many of the limitations related to the preparation of oxo amino acids from proteinogenic amino acids.

  DOI：

  10.1021/ol015520t

文献信息

• Masked Oxo Sulfinimines (<i>N</i>-Sulfinyl Imines) in the Asymmetric Synthesis of Proline and Pipecolic Acid Derivatives
  作者：Franklin A. Davis、Huiming Zhang、Seung H. Lee

  DOI：10.1021/ol015520t

  日期：2001.3.1

  [GRAPHICS]On addition of Et2AlCN/i-PrOH, masked oxo sulfinimines give alpha -amino nitriles that afford oxo alpha -amino acids on hydrolysis. These amino acids cyclize and are reduced to cis proline and cis pipecolic acids derivatives in high ee and good yield. This new procedure avoids many of the limitations related to the preparation of oxo amino acids from proteinogenic amino acids.