2-Propionyl-thiophen-carbaldehyd-(5) | 4565-26-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Propionyl-thiophen-carbaldehyd-(5)
• 英文别名: 5-Propionyl-2-thiophen-aldehyd；5-propionyl-thiophene-2-carbaldehyde；5-Propionyl-2-thiophene aldehyde；5-propanoylthiophene-2-carbaldehyde
• CAS: 4565-26-8
• 化学式: C₈H₈O₂S
• 分子量: 168.216
• InChiKey: VEWIPHSLMLKCDM-UHFFFAOYSA-N

物化性质

• 熔点：
  101-101.5 °C(Solvent: Heptane)
• 沸点：
  140 °C(Press: 2 Torr)
• 密度：
  1.214±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 在 六甲基磷酰三胺 、 三氢化钐 、 重铬酸吡啶 、 1,2-二碘乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 2-Propionyl-thiophen-carbaldehyd-(5)
  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.