(NE,R)-N-[3-(1,3-dioxolan-2-yl)propylidene]-2-methylpropane-2-sulfinamide | 781658-55-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (NE,R)-N-[3-(1,3-dioxolan-2-yl)propylidene]-2-methylpropane-2-sulfinamide
• CAS: 781658-55-7
• 化学式: C₁₀H₁₉NO₃S
• 分子量: 233.332
• InChiKey: ZULFSCHFAKYZJV-KDHUCADRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (NE,R)-N-[3-(1,3-dioxolan-2-yl)propylidene]-2-methylpropane-2-sulfinamide 在 N,N-二甲基丙烯基脲 、 dimethyl sulfide borane 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.75h， 生成 (R)-N-[(2S,3S)-1-amino-5-(1,3-dioxolan-2-yl)-2-(1,3-dioxolan-2-ylmethyl)pentan-3-yl]-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Self-Condensation of N-tert-Butanesulfinyl Aldimines:  Application to the Rapid Asymmetric Synthesis of Biologically Important Amine-Containing Compounds

  摘要：

  Highly diastereoselective intra- and intermolecular self-condensation reactions of N-tert-butanesulfinyl aldimines have been developed and applied to the rapid, asymmetric synthesis of trans-2-aminocyclopentanecarboxylic acid and the drug candidate SC-53116. Key to both syntheses is a novel microwave-assisted reaction in which N-sulfinyl aldimines are cleanly converted into nitriles in high-yielding concerted elimination processes.

  DOI：

  10.1021/ol048458j
• 作为产物：
  描述：

  2-(but-3-en-1-yl)-1,3-dioxolane 在 臭氧 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (NE,R)-N-[3-(1,3-dioxolan-2-yl)propylidene]-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Self-Condensation of N-tert-Butanesulfinyl Aldimines:  Application to the Rapid Asymmetric Synthesis of Biologically Important Amine-Containing Compounds

  摘要：

  Highly diastereoselective intra- and intermolecular self-condensation reactions of N-tert-butanesulfinyl aldimines have been developed and applied to the rapid, asymmetric synthesis of trans-2-aminocyclopentanecarboxylic acid and the drug candidate SC-53116. Key to both syntheses is a novel microwave-assisted reaction in which N-sulfinyl aldimines are cleanly converted into nitriles in high-yielding concerted elimination processes.

  DOI：

  10.1021/ol048458j