2-[Hydroxy-(4-methoxy-phenyl)-methyl]-thiophene-3-carbaldehyde | 173276-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[Hydroxy-(4-methoxy-phenyl)-methyl]-thiophene-3-carbaldehyde
• 英文别名: 2-[Hydroxy-(4-methoxyphenyl)methyl]thiophene-3-carbaldehyde
• CAS: 173276-66-9
• 化学式: C₁₃H₁₂O₃S
• 分子量: 248.302
• InChiKey: VGQHBQWQLGHGMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[Hydroxy-(4-methoxy-phenyl)-methyl]-thiophene-3-carbaldehyde 在 重铬酸吡啶 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 7-(4-Methoxy-phenyl)-thieno[2,3-d]pyridazine
  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 、 4-甲氧基苯甲醛 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 2.0h， 以43%的产率得到2-[Hydroxy-(4-methoxy-phenyl)-methyl]-thiophene-3-carbaldehyde
  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

文献信息

• 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：——
• 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.