5,5-Dimethyl-4-methylideneoxathiane 2-oxide | 152062-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫烷类
• 英文名称: 5,5-Dimethyl-4-methylideneoxathiane 2-oxide
• CAS: 152062-88-9
• 化学式: C₇H₁₂O₂S
• 分子量: 160.237
• InChiKey: ZJZLETXHWHRMMG-UHFFFAOYSA-N

物化性质

• 沸点：
  230.4±43.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-Dimethyl-4-methylideneoxathiane 2-oxide 在 m-CBPA 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到5,5-Dimethyl-4-methylideneoxathiane 2,2-dioxide
  参考文献：
  名称：

  Convenient Syntheses of Chiral Cyclic Sulfinates (Sultines) from Unsaturated Alcohols

  摘要：

  The reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonamide (TsNSO) is shown to lead stereoselectively to chiral cyclic or bicyclic sulfinates (sultines). The reactions occur at ambient temperatures and afford a general route to delta- and epsilon-sultines which are notable for their crystallinity and thermal stability. These studies confirm the preservation of stereochemical integrity of the carbon atom alpha to the oxygen atom in the sultine ring. Some unsaturated aldehydes furnish sultines via a tandem oxo-ene cyclization and subsequent ring closure to the sultine. In some reactions, N-toluenesulfonamide derivatives of sultines (compounds of type 11) were isolated, and since those were converted into the sultines by the action of BF3-OEt(2), such sulfonamides are considered to be intermediates in the reaction pathway.

  DOI：

  10.1021/jo00129a056
• 作为产物：
  描述：

  2,2,3-三甲基-丁-3-烯-1-醇 在 三氟化硼乙醚 、 N-亚硫酰基-p-甲苯磺胺 作用下， 以 苯 为溶剂， 反应 2.0h， 以64%的产率得到5,5-Dimethyl-4-methylideneoxathiane 2-oxide
  参考文献：
  名称：

  Stereocontrolled syntheses of novel cyclic sulfinates using N-sulfinyl-p-toiuenesulfonamide

  摘要：

  通过不饱和醇与 N-亚磺酰基对甲苯磺酰胺（TsNSO）的反应，可形成手性环状和双环硫酸盐（苏尔丁），并具有很高的立体选择性。

  DOI：

  10.1039/c39930001195

文献信息

• Convenient Syntheses of Chiral Cyclic Sulfinates (Sultines) from Unsaturated Alcohols
  作者：Charles M. Marson、Paul R. Giles

  DOI：10.1021/jo00129a056

  日期：1995.12

  The reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonamide (TsNSO) is shown to lead stereoselectively to chiral cyclic or bicyclic sulfinates (sultines). The reactions occur at ambient temperatures and afford a general route to delta- and epsilon-sultines which are notable for their crystallinity and thermal stability. These studies confirm the preservation of stereochemical integrity of the carbon atom alpha to the oxygen atom in the sultine ring. Some unsaturated aldehydes furnish sultines via a tandem oxo-ene cyclization and subsequent ring closure to the sultine. In some reactions, N-toluenesulfonamide derivatives of sultines (compounds of type 11) were isolated, and since those were converted into the sultines by the action of BF3-OEt(2), such sulfonamides are considered to be intermediates in the reaction pathway.
• Stereocontrolled syntheses of novel cyclic sulfinates using N-sulfinyl-p-toiuenesulfonamide
  作者：Charles M. Marson、Paul R. Giles、Harry Adams、Neil A. Bailey

  DOI：10.1039/c39930001195

  日期：——

  Chiral cyclic and bicyclic sulfinates (sultines) are formed with high stereoselection by the reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonamide (TsNSO).

  通过不饱和醇与 N-亚磺酰基对甲苯磺酰胺（TsNSO）的反应，可形成手性环状和双环硫酸盐（苏尔丁），并具有很高的立体选择性。