2-(p-Tolylsulfonyl-methyl)-tetrahydro-thiophene | 138643-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(p-Tolylsulfonyl-methyl)-tetrahydro-thiophene
• 英文别名: 2-[(4-methylphenyl)sulfonylmethyl]thiolane
• CAS: 138643-63-7
• 化学式: C₁₂H₁₆O₂S₂
• 分子量: 256.39
• InChiKey: BLWFFFHCTLLZFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  potassium thiotosylate 以 丙酮 为溶剂， 反应 16.0h， 生成 2-(p-Tolylsulfonyl-methyl)-tetrahydro-thiophene
  参考文献：
  名称：

  The cyclosulfonylation reaction: A comment on the radical reactions of 4-pentenyl tosylate

  摘要：

  Attempted free radical rearrangement of the para-toluenesulfonyl ester of 4-penten-1-ol in carbon tetrachloride gives only the simple Kharasch 1,2-adduct, instead of the 2-substituted tetrahydrofuran as claimed by Serra and da Silva Correa.

  DOI：

  10.1016/0040-4039(94)02446-i

文献信息

• Intramolecular homolytic substitution at the sulfur atom: an alternative way to generate phosphorus- and sulfur-centered radicals
  作者：Paola Carta、Nicolas Puljic、Carine Robert、Anne-Lise Dhimane、Cyril Ollivier、Louis Fensterbank、Emmanuel Lacôte、Max Malacria

  DOI：10.1016/j.tet.2008.08.108

  日期：2008.12

  Two efficient procedures involving tin hydride or thiophenol-mediated intramolecular homolytic substitution at the sulfur atom are reported. They lead to the generation of varied P(V)-centered radicals from the corresponding aryl or alkyne thiophosphorus substrates. The radical formed can be trapped by an olefin via an intermolecular addition, leading to the construction of C–P bonds. Thiophosphination

  报道了在硫原子上涉及氢化锡或硫酚介导的分子内均溶取代的两种有效方法。它们导致从相应的芳基或炔基硫代磷底物生成各种以P（V）为中心的基团。形成的自由基可以通过分子间加成被烯烃捕获，从而导致C-P键的构建。还使用自由基环异构化方法实现了三键的硫代磷酸化。检验了该方法对含硫物质的扩展。
• An interesting rearrangement of unsaturated sulphonate and thiosulphonate esters
  作者：Arménio C. Serra、Carlos M.M. da Silva Corrêa

  DOI：10.1016/0040-4039(91)80246-3

  日期：1991.11

  Alkenyl tosylates and thiotosylates, in the presence of radical initiators, undergo radical rearrangements to the corresponding tetrahydrofuran and tetrahydrothiophen derivatives.

  在自由基引发剂的存在下，烯基甲苯磺酸盐和巯基甲苯磺酸盐发生自由基重排，形成相应的四氢呋喃和四氢噻吩衍生物。
• The cyclosulfonylation reaction: A comment on the radical reactions of 4-pentenyl tosylate
  作者：Donald C Craig、Alexander Durie、Gavin L Edwards、David J Sinclair

  DOI：10.1016/0040-4039(94)02446-i

  日期：1995.2

  Attempted free radical rearrangement of the para-toluenesulfonyl ester of 4-penten-1-ol in carbon tetrachloride gives only the simple Kharasch 1,2-adduct, instead of the 2-substituted tetrahydrofuran as claimed by Serra and da Silva Correa.