5,5-dimethyl-1,3-dithiane monosulfoxide | 52168-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 5,5-dimethyl-1,3-dithiane monosulfoxide
• 英文别名: 5,5-Dimethyl-1,3-dithian-1-oxid；5,5-Dimethyl-1,3-dithiane 1-oxide
• CAS: 52168-60-2
• 化学式: C₆H₁₂OS₂
• 分子量: 164.293
• InChiKey: CIJCIXLVPJBCDI-UHFFFAOYSA-N

物化性质

• 沸点：
  327.2±31.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  新戊二醇二甲基硫酸酯 在 sodium sulfide 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 臭氧 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 81.5h， 生成 5,5-dimethyl-1,3-dithiane monosulfoxide
  参考文献：
  名称：

  Studies on the oxidation of 1, 3-dithiane and 5, 5-disubstituted analogues including X-ray crystal structure, equilibration studies and pK a measurements on selected oxides

  摘要：

  Oxidation of 1,3-dithiane has been carried out using eight different oxidants under several different reaction conditions. The most favourable conditions for obtaining the required trans-1,3-dithiane 1,3-dioxide were to use either MCPBA in Et(2)O or NaIO4 in MeOH-H2O. Other 5,5-disubstituted-1,3-dithianes were also prepared and subjected to similar oxidations. For these compounds the best oxidant for obtaining the trans-dioxides was O-3. A rationalisation for the stereochemical outcome of the oxidations is presented and requires that trans-1,3-dithiane 1,3-dioxide is more stable than cis-1,3-dithiane 1,3-dioxide. This is borne out by equilibration studies of the two diastereoisomeric sulfoxides using N2O4. A rationalisation for the greater stability of the trans compared to the cis isomer is also presented and fits with the pK(a) values and melting points of the two compounds.

  DOI：

  10.1039/p19940002363

文献信息

• Studies on the oxidation of 1, 3-dithiane and 5, 5-disubstituted analogues including X-ray crystal structure, equilibration studies and pK a measurements on selected oxides
  作者：Varinder K. Aggarwal、Ian W. Davies、Richard Franklin、John Maddock、Mary F. Mahon、Kieran C. Molloy

  DOI：10.1039/p19940002363

  日期：——

  Oxidation of 1,3-dithiane has been carried out using eight different oxidants under several different reaction conditions. The most favourable conditions for obtaining the required trans-1,3-dithiane 1,3-dioxide were to use either MCPBA in Et(2)O or NaIO4 in MeOH-H2O. Other 5,5-disubstituted-1,3-dithianes were also prepared and subjected to similar oxidations. For these compounds the best oxidant for obtaining the trans-dioxides was O-3. A rationalisation for the stereochemical outcome of the oxidations is presented and requires that trans-1,3-dithiane 1,3-dioxide is more stable than cis-1,3-dithiane 1,3-dioxide. This is borne out by equilibration studies of the two diastereoisomeric sulfoxides using N2O4. A rationalisation for the greater stability of the trans compared to the cis isomer is also presented and fits with the pK(a) values and melting points of the two compounds.