(S)-4-Isopropyl-3-((1S,2R)-2-mercapto-cyclohexanecarbonyl)-5,5-dimethyl-oxazolidin-2-one | 850733-75-4

• 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-3-((1S,2R)-2-mercapto-cyclohexanecarbonyl)-5,5-dimethyl-oxazolidin-2-one
• 英文别名: (4S)-5,5-dimethyl-4-propan-2-yl-3-[(1S,2R)-2-sulfanylcyclohexanecarbonyl]-1,3-oxazolidin-2-one
• CAS: 850733-75-4
• 化学式: C₁₅H₂₅NO₃S
• 分子量: 299.434
• InChiKey: OUNGBXZYRGHWPL-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-Isopropyl-3-((1S,2R)-2-mercapto-cyclohexanecarbonyl)-5,5-dimethyl-oxazolidin-2-one 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 ((1S,2R)-2-Methylsulfanyl-cyclohexyl)-methanol
  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：

  Cyclohex-1-enyl-((S)-4-isopropyl-5,5-dimethyl-2-thioxo-oxazolidin-3-yl)-methanone 在 四氯化锡 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.0h， 以52%的产率得到(S)-4-Isopropyl-3-((1S,2R)-2-mercapto-cyclohexanecarbonyl)-5,5-dimethyl-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