3-((Z)-2-Methylsulfanyl-vinyl)-5-thiophen-3-yl-2,5-dihydro-furan-2-ol | 220338-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-((Z)-2-Methylsulfanyl-vinyl)-5-thiophen-3-yl-2,5-dihydro-furan-2-ol
• 英文别名: 3-[(Z)-2-methylsulfanylethenyl]-5-thiophen-3-yl-2,5-dihydrofuran-2-ol
• CAS: 220338-00-1
• 化学式: C₁₁H₁₂O₂S₂
• 分子量: 240.347
• InChiKey: KLBYDRJBHMEUMY-RQOWECAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-((Z)-2-Methylsulfanyl-vinyl)-5-thiophen-3-yl-2,5-dihydro-furan-2-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以82%的产率得到3-((Z)-2-Methylsulfanyl-vinyl)-5-thiophen-3-yl-5H-furan-2-one
  参考文献：
  名称：

  Coupling Reactions and Coupling−Alkylations of Thiophenecarbaldehydes Promoted by Samarium Diiodide

  摘要：

  The coupling reactions of 2-thiophenecarbaldehyde with aromatic or aliphatic aldehydes were promoted by samarium diiodide in the presence of hexamethylphosphoramide to give C-5 hydroxyalkylation products. The coupling reactions of 3-thiophenecarbaldehyde occurred at C-2, and the subsequent alkylations occurred at the sulfur atom, accompanied by a concurrent opening of the thiophene ring to afford gamma-lactols. Double hydroxyalkylations of 2- and 3-thiophenecarbaldehydes were also carried out under appropriate reaction conditions. Synthetic applications of these thiophenecarbonyl coupling products were demonstrated, for example, by elaboration to furans, butenolides, and thiophene-fused polycyclic compounds.

  DOI：

  10.1021/jo980851d
• 作为产物：
  描述：

  3-噻吩甲醛 、 碘甲烷 在 三氢化钐 、 1,2-二碘乙烷 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 27.0h， 以74%的产率得到3-((Z)-2-Methylsulfanyl-vinyl)-5-thiophen-3-yl-2,5-dihydro-furan-2-ol
  参考文献：
  名称：

  Coupling Reactions and Coupling−Alkylations of Thiophenecarbaldehydes Promoted by Samarium Diiodide

  摘要：

  The coupling reactions of 2-thiophenecarbaldehyde with aromatic or aliphatic aldehydes were promoted by samarium diiodide in the presence of hexamethylphosphoramide to give C-5 hydroxyalkylation products. The coupling reactions of 3-thiophenecarbaldehyde occurred at C-2, and the subsequent alkylations occurred at the sulfur atom, accompanied by a concurrent opening of the thiophene ring to afford gamma-lactols. Double hydroxyalkylations of 2- and 3-thiophenecarbaldehydes were also carried out under appropriate reaction conditions. Synthetic applications of these thiophenecarbonyl coupling products were demonstrated, for example, by elaboration to furans, butenolides, and thiophene-fused polycyclic compounds.

  DOI：

  10.1021/jo980851d