2-hydroxy-1-(1-methylpyrrol-2-yl)-2-(3-thienyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-1-(1-methylpyrrol-2-yl)-2-(3-thienyl)ethanone
• 英文别名: 2-Hydroxy-1-(1-methylpyrrol-2-yl)-2-thiophen-3-ylethanone
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: UIGRQFYDFPYRSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-噻吩甲醛 在 N-甲基-2-吡咯甲醛 、 六甲基磷酰三胺 、 三氢化钐 、 1,2-二碘乙烷 作用下， 生成 3-噻吩甲醇 、 2-<1-hydroxy-(3-thienyl)methyl>thiophene-3-carbaldehyde 、 2-hydroxy-1-(1-methylpyrrol-2-yl)-2-(3-thienyl)ethanone 、 2-[Hydroxy-(1-methylpyrrol-2-yl)methyl]thiophene-3-carbaldehyde
  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.