ethyl 3-ethyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 3-ethyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylate
• 英文别名: Ethyl 3-ethyl-4,9-dioxobenzo[f][1]benzothiole-2-carboxylate；ethyl 3-ethyl-4,9-dioxobenzo[f][1]benzothiole-2-carboxylate
• 化学式: C₁₇H₁₄O₄S
• 分子量: 314.362
• InChiKey: AKUYXZMTUQCORP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(1,4-dihydroxynaphthalen-2-yl)propan-1-one 在 盐酸 、 air 、 silica gel 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙酸乙酯 为溶剂， 反应 3.25h， 生成 ethyl 3-ethyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylate
  参考文献：
  名称：

  An Improved Method for the Preparation of 4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates from 2-Acyl-1,4-benzoquinones and Mercaptoacetates

  摘要：

  4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates (4) have been synthesized in a one-pot procedure from 2-acyl-1,4-benzoquinones (1) and mercaptoacetates (2) by using 1-trimethylsilylimidazole as a protective reagent as well as a base. Thus, reaction of 1 with 2 in THF at room temperature was followed by treatment with excess of 1-trimethylsilylimidazole at 80 degreesC. Then the cooled mixture was hydrolyzed with hydrochloric acid and oxidized with cerium(IV) ammonium nitrate (CAN) to give the expected thiophenequinone derivatives (4). 4,9-Dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylates (7) were similarly prepared from 2-acyl-1,4-naphthoquinones (5) and mercaptoacetates, in general, by omitting the CAN oxidation procedure.

  DOI：

  10.3987/com-01-9358

文献信息

• An Improved Method for the Preparation of 4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates from 2-Acyl-1,4-benzoquinones and Mercaptoacetates
  作者：Kazuhiro Kobayashi、Keiichi Yoneda、Masaharu Uchida、Hideki Matsuoka、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.3987/com-01-9358

  日期：——

  4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates (4) have been synthesized in a one-pot procedure from 2-acyl-1,4-benzoquinones (1) and mercaptoacetates (2) by using 1-trimethylsilylimidazole as a protective reagent as well as a base. Thus, reaction of 1 with 2 in THF at room temperature was followed by treatment with excess of 1-trimethylsilylimidazole at 80 degreesC. Then the cooled mixture was hydrolyzed with hydrochloric acid and oxidized with cerium(IV) ammonium nitrate (CAN) to give the expected thiophenequinone derivatives (4). 4,9-Dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylates (7) were similarly prepared from 2-acyl-1,4-naphthoquinones (5) and mercaptoacetates, in general, by omitting the CAN oxidation procedure.