4-methyl-2-thiophen-2-yl-3,6-dihydro-2H-thiopyran | 136912-31-7

• 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: 4-methyl-2-thiophen-2-yl-3,6-dihydro-2H-thiopyran
• CAS: 136912-31-7
• 化学式: C₁₀H₁₂S₂
• 分子量: 196.337
• InChiKey: DRMRRFRDFIPJQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 天然橡胶 在 双(三甲基硫化硅) 、 cobalt(II) chloride 作用下， 以 乙腈 为溶剂， 生成 5-methyl-2-thiophen-2-yl-3,6-dihydro-2H-thiopyran 、 4-methyl-2-thiophen-2-yl-3,6-dihydro-2H-thiopyran
  参考文献：
  名称：

  Silicon-assisted synthesis of thiocarbonyl derivatives and reactivity of dienophilic thioaldehydes

  摘要：

  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.

  DOI：

  10.1021/jo00026a025

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.