2-<1-hydroxy-(3-thienyl)methyl>thiophene-3-carbaldehyde | 173276-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<1-hydroxy-(3-thienyl)methyl>thiophene-3-carbaldehyde
• 英文别名: 2-(α-Hydroxy-3-thienylmethyl)thiophene-3-carbaldehyde；2-[Hydroxy(thiophen-3-yl)methyl]thiophene-3-carbaldehyde
• CAS: 173276-64-7
• 化学式: C₁₀H₈O₂S₂
• 分子量: 224.304
• InChiKey: YLSDCVNSQBPHPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<1-hydroxy-(3-thienyl)methyl>thiophene-3-carbaldehyde 在 劳森试剂 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以85%的产率得到6-(thiophen-3-yl)thieno[3,4-b]thiophene
  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 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 2-<1-hydroxy-(3-thienyl)methyl>thiophene-3-carbaldehyde
  参考文献：
  名称：

  An Efficient Synthesis of Heterocyclic Analogs of 1-Arylnaphthalene Lignans

  摘要：

  The heterocyclic analogs 5a-f, 16, and 20 of 1-arylnaphthalene lignans were synthesized by Diels-Alder reactions of acetoxy aldehydes 11a-f, 14, and 18 with dimethyl acetylenedicarboxylate. A pathway for formation of 5a-f, 16, and 20 through the intermediacy of heteroaromatic isobenzofurans derived from acetoxy aldehydes is discussed.

  DOI：

  10.1021/jo00103a029

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.
• An Efficient Synthesis of Heterocyclic Analogs of 1-Arylnaphthalene Lignans
  作者：Tooru Kuroda、Masami Takahashi、Tsuyoshi Ogiku、Hiroshi Ohmizu、Takashi Nishitani、Kazuhiko Kondo、Tameo Iwasaki

  DOI：10.1021/jo00103a029

  日期：1994.12

  The heterocyclic analogs 5a-f, 16, and 20 of 1-arylnaphthalene lignans were synthesized by Diels-Alder reactions of acetoxy aldehydes 11a-f, 14, and 18 with dimethyl acetylenedicarboxylate. A pathway for formation of 5a-f, 16, and 20 through the intermediacy of heteroaromatic isobenzofurans derived from acetoxy aldehydes is discussed.