(R)-2-methyl-N-(1-morpholinoethylidene)propane-2-sulfinamide | 817576-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (R)-2-methyl-N-(1-morpholinoethylidene)propane-2-sulfinamide
• CAS: 817576-12-8
• 化学式: C₁₀H₂₀N₂O₂S
• 分子量: 232.347
• InChiKey: PRVCQFIVUJGARH-OAHLLOKOSA-N

物化性质

• 熔点：
  39-42 °C
• 沸点：
  355.4±52.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  41.9
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,4,4-三氟-2-丁酸乙酯 、 (R)-2-methyl-N-(1-morpholinoethylidene)propane-2-sulfinamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到(S)-ethyl 5-((R)-tert-butanesulfinylimino)-5-morpholino-3-(trifluoromethyl)pentanoate
  参考文献：
  名称：

  Michael addition of N-sulfinyl metalloenamines to β-trifluoromethyl-α,β-unsaturated ester: an efficient access to chiral 4-trifluoromethyl-2-piperidones

  摘要：

  Michael addition of N-sulfinyl metalloenamines to beta-trifluoromethyl-alpha, beta-unsaturated ester was investigated. High diastereoselectivities and excellent yields were obtained. The conversion of addition products into 4-trifluoromethyl-2-piperidones asymmetrically, which involved a DIBAL-H reduction and the following cyclization, was illustrated. The absolute configuration of Michael addition products and 4-trifluoromethyl-2-piperidones were determined by X-ray crystallographic analysis and NOESY experiment, respectively. This method affords an efficient and asymmetric approach to a variety of chiral 4-trifluoromethyl-2-piperidones. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.047