3-((Z)-2-Benzylsulfanyl-vinyl)-5-thiophen-3-yl-2,5-dihydro-furan-2-ol | 220337-99-5

• 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: 3-((Z)-2-Benzylsulfanyl-vinyl)-5-thiophen-3-yl-2,5-dihydro-furan-2-ol
• 英文别名: 3-[(Z)-2-benzylsulfanylethenyl]-5-thiophen-3-yl-2,5-dihydrofuran-2-ol
• CAS: 220337-99-5
• 化学式: C₁₇H₁₆O₂S₂
• 分子量: 316.445
• InChiKey: GDVSNTPHFLYQFF-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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-Benzylsulfanyl-vinyl)-5-thiophen-3-yl-2,5-dihydro-furan-2-ol 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 0.08h， 以100%的产率得到(Z)-3-(2-benzylsulfanyl)ethenyl-5-(3-thienyl)furan
  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 在 六甲基磷酰三胺 、 三氢化钐 、 1,2-二碘乙烷 作用下， 反应 24.17h， 生成 3-((Z)-2-Benzylsulfanyl-vinyl)-5-thiophen-3-yl-2,5-dihydro-furan-2-ol
  参考文献：
  名称：

  Yang, Shyn-Ming; Fang, Jim-Min, Journal of the Chemical Society. Perkin transactions I, 1995, # 21, p. 2669 - 2672

  摘要：

  DOI：

文献信息

• Coupling Reactions and Coupling−Alkylations of Thiophenecarbaldehydes Promoted by Samarium Diiodide
  作者：Shyh-Ming Yang、Jim-Min Fang

  DOI：10.1021/jo980851d

  日期：1999.1.1

  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.
• Yang, Shyn-Ming; Fang, Jim-Min, Journal of the Chemical Society. Perkin transactions I, 1995, # 21, p. 2669 - 2672
  作者：Yang, Shyn-Ming、Fang, Jim-Min

  DOI：——

  日期：——