(S)-4-Isopropyl-5,5-dimethyl-3-((2S,3S)-2-methyl-3-methylsulfanyl-3-phenyl-propionyl)-oxazolidin-2-one | 850733-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-4-Isopropyl-5,5-dimethyl-3-((2S,3S)-2-methyl-3-methylsulfanyl-3-phenyl-propionyl)-oxazolidin-2-one
• 英文别名: (4S)-5,5-dimethyl-3-[(2S,3S)-2-methyl-3-methylsulfanyl-3-phenylpropanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 850733-78-7
• 化学式: C₁₉H₂₇NO₃S
• 分子量: 349.494
• InChiKey: LTVOBNOCMQTIJF-KBMXLJTQSA-N

物化性质

• 沸点：
  475.9±38.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-Isopropyl-5,5-dimethyl-3-((2S,3S)-2-methyl-3-methylsulfanyl-3-phenyl-propionyl)-oxazolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S)-2-Methyl-3-methylsulfanyl-3-phenyl-propan-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of 3-methylthio alcohols by intramolecular Michael addition reactions

  摘要：

  Chiral 3-methylthio alcohols have been synthesized through a known intramolecular sulfur transfer reaction that has been carried out in di- and trisubstituted alpha,beta-unsaturated N-enoyl oxazolidinethiones as substrates, giving rise to synlanti-diastereomers. The anti-diastereomer is favored and obtained via a highly diastereo-selective protonation step (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.021
• 作为产物：
  描述：

  (E)-1-((S)-4-Isopropyl-5,5-dimethyl-2-thioxo-oxazolidin-3-yl)-2-methyl-3-phenyl-propenone 在 niobium pentachloride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成 (S)-4-Isopropyl-5,5-dimethyl-3-((2S,3S)-2-methyl-3-methylsulfanyl-3-phenyl-propionyl)-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 3-methylthio alcohols by intramolecular Michael addition reactions

  摘要：

  Chiral 3-methylthio alcohols have been synthesized through a known intramolecular sulfur transfer reaction that has been carried out in di- and trisubstituted alpha,beta-unsaturated N-enoyl oxazolidinethiones as substrates, giving rise to synlanti-diastereomers. The anti-diastereomer is favored and obtained via a highly diastereo-selective protonation step (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.021