1,4-bis(3,6-dihydro-4,5-dimethyl-2H-thiopyranyl)benzene | 136912-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 1,4-bis(3,6-dihydro-4,5-dimethyl-2H-thiopyranyl)benzene
• 英文别名: 2-[4-(4,5-dimethyl-3,6-dihydro-2H-thiopyran-2-yl)phenyl]-4,5-dimethyl-3,6-dihydro-2H-thiopyran
• CAS: 136912-26-0
• 化学式: C₂₀H₂₆S₂
• 分子量: 330.558
• InChiKey: HUWXUOJLTGJSGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  对苯二甲醛 、 2,3-二甲基-1,3-丁二烯 在 cobalt(II) chloride hexahydrate 、 双(三甲基硫化硅) 、 1-乙基-3-甲基咪唑三氟甲磺酸盐 作用下， 以70%的产率得到1,4-bis(3,6-dihydro-4,5-dimethyl-2H-thiopyranyl)benzene
  参考文献：
  名称：

  离子液体作为基于 HMDST 的硫醛合成的替代反应介质

  摘要：

  图形摘要摘要 双（三甲基甲硅烷基）硫化物 (HMDST) 与醛的反应可以在 CoCl2·6H2O 或 TfOTMF 催化下在各种离子液体中有效地进行，导致硫醛的形成，硫醛被作为 Diels-Alder 环加合物捕获。当使用 1,3- 环己二烯时，总是能立体选择性地进入内异构体。

  DOI：

  10.1080/10426507.2015.1114487

文献信息

• Silicon-assisted synthesis of thiocarbonyl derivatives and reactivity of dienophilic thioaldehydes
  作者：Antonella Capperucci、Alessandro Degl'Innocenti、Alfredo Ricci、Alessandro Mordini、Gianna Reginato

  DOI：10.1021/jo00026a025

  日期：1991.12

  Treatment of bis(trimethylsilyl) sulfide with CoCl2.6H2O in the presence of aldehydes affords the corresponding thiocarbonyl analogues which can be trapped to avoid polymerization. The sulfurization reaction also takes place in the presence of TfOSiMe3, in which case, besides thioaldehydes, thioketones may be obtained in satisfactory yields. When thioaldehydes are generated with the CoCl2.6H2O method the Diels-Alder reaction with cyclohexadiene occurs with very high selectivity in favor of the endo isomer, whereas when the TfOSiMe3-based method is employed, the stereochemistry of the cycloadduct can be conveniently selected toward endo or exo by varying the molar ratio of the sulfurating agent.
• Ionic liquids as an alternative reaction medium for HMDST based synthesis of thioaldehydes
  作者：Damiano Tanini、Andrea Angeli、Antonella Capperucci

  DOI：10.1080/10426507.2015.1114487

  日期：2016.2.1

  Abstract Reaction of bis(trimethylsilyl)sulfide (HMDST) with aldehydes can be efficiently carried out in various ionic liquids, under CoCl2.6H2O or TfOTMF catalysis, leading to the formation of thioaldehydes, which are trapped as Diels-Alder cycloadducts. When 1,3-cycloheaxadiene was used, a stereoselective entry to the endo isomer was always obtained.

  图形摘要摘要 双（三甲基甲硅烷基）硫化物 (HMDST) 与醛的反应可以在 CoCl2·6H2O 或 TfOTMF 催化下在各种离子液体中有效地进行，导致硫醛的形成，硫醛被作为 Diels-Alder 环加合物捕获。当使用 1,3- 环己二烯时，总是能立体选择性地进入内异构体。