1,3-oxathiane 3,3-dioxide | 109577-03-9

• 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: 1,3-oxathiane 3,3-dioxide
• 英文别名: 1,3-oxathiane sulfone；2,4-butane sultone；1,3lambda~6~-Oxathiane-3,3-dione
• CAS: 109577-03-9
• 化学式: C₄H₈O₃S
• 分子量: 136.172
• InChiKey: CFROQNJYXPQWPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 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：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-oxathiane 3,3-dioxide 在 正丁基锂 、 乙酸-D3 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 、
  参考文献：
  名称：

  Does an Oxygen Function Stabilize the Sulfonyl Carbanion? Metalation of 1,3-Oxathiane 3,3-Dioxides

  摘要：

  1,3-氧硫杂环己烷3,3-二氧化物不是在C-2处锂化，而是优先在C-4处锂化，这表明氧官能团使该环系统中的磺酰碳负离子不稳定。

  DOI：

  10.1246/cl.1986.1655
• 作为产物：
  描述：

  1,3-氧硫杂环已烷 在 叔丁基过氧化氢 、 molybdenyl acetylacetonate 作用下， 以83%的产率得到1,3-oxathiane 3,3-dioxide
  参考文献：
  名称：

  Does an Oxygen Function Stabilize the Sulfonyl Carbanion? Metalation of 1,3-Oxathiane 3,3-Dioxides

  摘要：

  1,3-氧硫杂环己烷3,3-二氧化物不是在C-2处锂化，而是优先在C-4处锂化，这表明氧官能团使该环系统中的磺酰碳负离子不稳定。

  DOI：

  10.1246/cl.1986.1655

文献信息

• [EN] METHODS AND COMPOSITIONS FOR TREATING AMYLOID-RELATED DISEASES<br/>[FR] METHODES ET COMPOSITIONS POUR TRAITER LES MALADIES LIEES A L'AMYLOIDE
  申请人：NEUROCHEM INT LTD

  公开号：WO2004113275A3

  公开（公告）日：2005-10-27
• Calorimetric and Computational Study of 1,3- and 1,4-Oxathiane Sulfones
  作者：María Victoria Roux、Manuel Temprado、Pilar Jiménez、Rafael Notario、Ramón Guzmán-Mejía、Eusebio Juaristi

  DOI：10.1021/jo0618472

  日期：2007.2.1

  The enthalpies of formation in the condensed and gas states, Delta H-f degrees(m)(cd) and Delta H-f degrees(m)(g), of 1,3- and 1,4-oxathiane sulfones were derived from their respective enthalpies of combustion in oxygen, measured by a rotating bomb calorimeter and the variation of vapor pressures with temperatures determined by the Knudsen effusion technique. Standard ab initio molecular orbital calculations at the G2(MP2) and G3 levels were performed, and a theoretical study on molecular and electronic structure of the compounds has been carried out. Calculated Delta H-f degrees(m)(g) values at the G3 level using atomization reactions agree well with the experimental ones. These experimental and theoretical studies support that the destabilization found in 1,3-oxathiane sulfone, 11.2 kJ mol(-1) respecting to 1,4-oxathiane sulfone, is due to the electrostatic repulsion between the negative charges of the axial oxygen of the sulfone and the oxygen of the ring and apparently masks any stabilization originating from the hyperconjugative n(O) -> sigma*(C-SO2) stereoelectronic interaction.