[1-[[1-(Acetyloxymethyl)cyclohexyl]disulfanyl]cyclohexyl]methyl acetate | 935676-91-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [1-[[1-(Acetyloxymethyl)cyclohexyl]disulfanyl]cyclohexyl]methyl acetate
• CAS: 935676-91-8
• 化学式: C₁₈H₃₀O₄S₂
• 分子量: 374.566
• InChiKey: HQILNLKGLAJJCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [1-[[1-(Acetyloxymethyl)cyclohexyl]disulfanyl]cyclohexyl]methyl acetate 在 Shi's ketone 、 edetate disodium Oxone 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以97%的产率得到[1-[(S)-[1-(acetyloxymethyl)cyclohexyl]sulfinyl]sulfanylcyclohexyl]methyl acetate
  参考文献：
  名称：

  Enantioselective Organocatalytic Oxidation of Functionalized Sterically Hindered Disulfides

  摘要：

  The first study on enantioselective oxidation of functionalized sterically hindered disulfides is reported. This study shows that the Shi organocatalytic system using carbohydrate-derived ketone with oxone is superior to the Ellman-Bolm vanadium catalyst in terms of chemical yield and enantioselectivity. Whereas the latter system afforded mostly racemic thiosulfinates in low to moderate yields, the former one afforded thiosulfinates with up to 96% ee.

  DOI：

  10.1021/ol070056z
• 作为产物：
  描述：

  1-[(2-formylcyclohexyl)disulfanyl]cyclohexanecarbaldehyde 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 48.5h， 生成 [1-[[1-(Acetyloxymethyl)cyclohexyl]disulfanyl]cyclohexyl]methyl acetate
  参考文献：
  名称：

  Enantioselective Organocatalytic Oxidation of Functionalized Sterically Hindered Disulfides

  摘要：

  The first study on enantioselective oxidation of functionalized sterically hindered disulfides is reported. This study shows that the Shi organocatalytic system using carbohydrate-derived ketone with oxone is superior to the Ellman-Bolm vanadium catalyst in terms of chemical yield and enantioselectivity. Whereas the latter system afforded mostly racemic thiosulfinates in low to moderate yields, the former one afforded thiosulfinates with up to 96% ee.

  DOI：

  10.1021/ol070056z