4-Hydroxy-5,6-bis(methoxycarbonyl)-7-(p-tolyl)benzothiophene | 138589-43-2

• 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: 4-Hydroxy-5,6-bis(methoxycarbonyl)-7-(p-tolyl)benzothiophene
• 英文别名: Dimethyl 4-hydroxy-7-(4-methylphenyl)-1-benzothiophene-5,6-dicarboxylate
• CAS: 138589-43-2
• 化学式: C₁₉H₁₆O₅S
• 分子量: 356.399
• InChiKey: YBWPHZKTUBKXQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(α-Hydroxy-4-methylbenzyl)thiophene-3-carbaldehyde 在 三氟乙酸 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 4-Hydroxy-5,6-bis(methoxycarbonyl)-7-(p-tolyl)benzothiophene
  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

• A new method for generation of 4- and 6-aryl thieno[2,3-c]furans, and 3-aryl furo[3,4-b]pyridine
  作者：Tooru Kuroda、Masami Takahashi、Tsuyoshi Ogiku、Hiroshi Ohtnizu、Kazuhiko Kondo、Tameo Iwasaki

  DOI：10.1039/c39910001635

  日期：——

  6-Aryl thieno[2,3-c]furans 2a–c, 4-(3,4-dimethoxyphenyl)thieno[2,3-c]furan 3a, and 3-(3,4-dimethoxyphenyl)furo[3,4-b]pyridine 4a, which were intercepted in situ by dimethyl acetylenedicarboxylate to give the corresponding Diels–Alder adducts in good yields, were generated under acidic conditions from 2-(α-acetoxybenzyl)thiophene-3-carbaldehydes 5a–c, 3-(α-acetoxy-3,4-dimethoxybenzyl)thiophene-2-carbaldehyde 10a and 2-(α-acetoxy-3,4-dimethoxybenzyl)pyridine-3-carbaldehyde 12a, respectively.

  6 芳基噻吩并[2,3-c]呋喃 2a-c、4-(3,4-二甲氧基苯基)噻吩并[2,3-c]呋喃 3a 和 3-(3,4-二甲氧基苯基)呋喃并[3,4-b]吡啶 4a 被乙炔二羧酸二甲酯原位截取，以良好的产率得到相应的 Diels-Alder 加合物、在酸性条件下，分别由 2-(α-乙酰氧基苄基)噻吩-3-甲醛 5a-c、3-(α-乙酰氧基-3,4-二甲氧基苄基)噻吩-2-甲醛 10a 和 2-(α-乙酰氧基-3,4-二甲氧基苄基)吡啶-3-甲醛 12a 生成。
• 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.