(S)-(+)-N-[5,5-(ethylenedioxy)hexanylidene]-p-toluenesulfinamide | 332072-73-8

• 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-[5,5-(ethylenedioxy)hexanylidene]-p-toluenesulfinamide
• 英文别名: (NE,S)-4-methyl-N-[4-(2-methyl-1,3-dioxolan-2-yl)butylidene]benzenesulfinamide
• CAS: 332072-73-8
• 化学式: C₁₅H₂₁NO₃S
• 分子量: 295.403
• InChiKey: VAZBADAJMAGWKE-QGRTWZNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(+)-N-[5,5-(ethylenedioxy)hexanylidene]-p-toluenesulfinamide 在 palladium on activated charcoal 盐酸 、 氢气 、 异丙醇 作用下， 以 四氢呋喃 、 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 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-(+)-N-[5,5-(ethylenedioxy)hexanylidene]-p-toluenesulfinamide
  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

• Asymmetric Synthesis of Cyclic α-Amino Phosphonates Using Masked Oxo Sulfinimines (<i>N</i>-Sulfinyl Imines)
  作者：Franklin A. Davis、Seung H. Lee、He Xu

  DOI：10.1021/jo040127x

  日期：2004.5.1

  Five-, six-, and seven-membered cyclic α-amino phosphonates, amino acid surrogates, are prepared in enantiomerically pure form via the highly diastereomeric addition of metal phosphonates to masked oxo sulfinimines. Hydrolysis of the resulting masked oxo α-amino phosphonates followed by reduction of the intermediate cyclic imino phosphonates affords the title compounds in good yield.

  五，六和七元环状α-氨基膦酸酯（氨基酸替代物）是通过将金属膦酸酯高度非对映异构体加到被掩盖的氧亚磺胺上而制成对映体纯形式的。水解所得的掩蔽的羰基α-氨基膦酸酯，然后还原中间体环状亚氨基膦酸酯，以良好的收率得到标题化合物。
• 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.