(R)-N-(7-bromo-2-oxoindolin-3-ylidene)-2-methylpropane-2-sulfinamide | 1620748-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (R)-N-(7-bromo-2-oxoindolin-3-ylidene)-2-methylpropane-2-sulfinamide
• CAS: 1620748-38-0
• 化学式: C₁₂H₁₃BrN₂O₂S
• 分子量: 329.217
• InChiKey: LPYOALDTVUJBAG-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  三甲基氰硅烷 、 (R)-N-(7-bromo-2-oxoindolin-3-ylidene)-2-methylpropane-2-sulfinamide 在 magnesium bromide ethyl etherate 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以98%的产率得到(R)-N-((S)-7-bromo-3-cyano-2-oxoindolin-3-yl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Lewis Acid Promoted Diastereoselective Addition of TMSCN and TMSCF₃ to Isatin-Derived N-Sulfinyl Ketimines: Synthesis of Optically Active Tetrasubstituted 3-Aminooxindoles

  摘要：

  A practical and efficient method for preparation of highly enantiomerically enriched 3-cyano-3-aminocaindoles and 3-trifluoromethyl-3-aminooxindoles with up to 99% optical purity by a Lewis acid promoted diastereoselective Strecker reaction and trifluoromethylation of isatin-derived N-tert-butanesulfinyl ketimines has been developed. This protocol allows direct use of N-free isatin substrates under mild conditions.

  DOI：

  10.1021/jo501360g
• 作为产物：
  描述：

  7-溴靛红 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-N-(7-bromo-2-oxoindolin-3-ylidene)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Lewis Acid Promoted Diastereoselective Addition of TMSCN and TMSCF₃ to Isatin-Derived N-Sulfinyl Ketimines: Synthesis of Optically Active Tetrasubstituted 3-Aminooxindoles

  摘要：

  A practical and efficient method for preparation of highly enantiomerically enriched 3-cyano-3-aminocaindoles and 3-trifluoromethyl-3-aminooxindoles with up to 99% optical purity by a Lewis acid promoted diastereoselective Strecker reaction and trifluoromethylation of isatin-derived N-tert-butanesulfinyl ketimines has been developed. This protocol allows direct use of N-free isatin substrates under mild conditions.

  DOI：

  10.1021/jo501360g