2-Methyl-propane-2-sulfinic acid [(1S,2R)-2-cyano-3-[1,3]dioxolan-2-yl-1-(2-[1,3]dioxolan-2-yl-ethyl)-propyl]-amide | 781658-58-0

• 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: 2-Methyl-propane-2-sulfinic acid [(1S,2R)-2-cyano-3-[1,3]dioxolan-2-yl-1-(2-[1,3]dioxolan-2-yl-ethyl)-propyl]-amide
• 英文别名: (R)-N-[(2R,3S)-2-cyano-1,5-bis(1,3-dioxolan-2-yl)pentan-3-yl]-2-methylpropane-2-sulfinamide
• CAS: 781658-58-0
• 化学式: C₁₆H₂₈N₂O₅S
• 分子量: 360.475
• InChiKey: QBMWUVMWYDSQSU-LUFVGAHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-Methyl-propane-2-sulfinic acid [(1S,2R)-2-cyano-3-[1,3]dioxolan-2-yl-1-(2-[1,3]dioxolan-2-yl-ethyl)-propyl]-amide 在 platinum(IV) oxide dimethyl sulfide borane 、 氢气 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.67h， 生成 4-amino-5-chloro-N-[(hexahydro-1H-pyrrolizin-1-yl)methyl]-2-methoxybenzamide
  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：

  以 乙腈 为溶剂， 反应 0.25h， 以84%的产率得到2-Methyl-propane-2-sulfinic acid [(1S,2R)-2-cyano-3-[1,3]dioxolan-2-yl-1-(2-[1,3]dioxolan-2-yl-ethyl)-propyl]-amide
  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