N-((S,S(S))-3-hydroxy-2-(pentan-3-yloxy)propylidene)-2-methylpropane-2-sulfinamide | 1226768-11-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: N-((S,S(S))-3-hydroxy-2-(pentan-3-yloxy)propylidene)-2-methylpropane-2-sulfinamide
• CAS: 1226768-11-1
• 化学式: C₁₂H₂₅NO₃S
• 分子量: 263.401
• InChiKey: JQLUVCFMMOPXPB-GTNSWQLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  58.89
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  硝基甲烷 、 N-((S,S(S))-3-hydroxy-2-(pentan-3-yloxy)propylidene)-2-methylpropane-2-sulfinamide 在 sodium hydroxide 作用下， 反应 24.0h， 生成 N-((2S,3S,S(S))-4-hydroxy-1-nitro-3-(pentan-3-yloxy)butan-2-yl)-2-methylpropane-2-sulfinamide 、 N-((2R,3S,S(S))-4-hydroxy-1-nitro-3-(pentan-3-yloxy)butan-2-yl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  A Practical and Azide-Free Synthetic Approach to Oseltamivir from Diethyl d-Tartrate

  摘要：

  A short and practical synthesis of oseltamivir was accomplished in 11 steps from inexpensive and abundant diethyl D-tartrate starting material. This azide-free route featured an asymmetric aza-Henry reaction and a domino nitro-Michael/Horner-Wadsworth-Emmons (HWE) reaction as the key steps to construct the relevant cyclohexene ring of the product, which provided an economical and practical alternative for the synthesis of oseltamivir.

  DOI：

  10.1021/jo100187m
• 作为产物：
  描述：

  (R)-3-hydroxy-2-(pentan-3-yloxy)propanal 、 S-叔丁基亚磺酰胺 在 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以73%的产率得到N-((S,S(S))-3-hydroxy-2-(pentan-3-yloxy)propylidene)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  A Practical and Azide-Free Synthetic Approach to Oseltamivir from Diethyl d-Tartrate

  摘要：

  A short and practical synthesis of oseltamivir was accomplished in 11 steps from inexpensive and abundant diethyl D-tartrate starting material. This azide-free route featured an asymmetric aza-Henry reaction and a domino nitro-Michael/Horner-Wadsworth-Emmons (HWE) reaction as the key steps to construct the relevant cyclohexene ring of the product, which provided an economical and practical alternative for the synthesis of oseltamivir.

  DOI：

  10.1021/jo100187m