4,6-dihydrothieno<3,4-b>furan | 164797-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4,6-dihydrothieno<3,4-b>furan
• 英文别名: dihydrothieno[3,4-b]furan；4,6-Dihydrothieno[3,4-b]furan
• CAS: 164797-57-3
• 化学式: C₆H₆OS
• 分子量: 126.179
• InChiKey: GIDSMZAFBFGELB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6-dihydrothieno<3,4-b>furan 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 thieno<3,4-b>furan
  参考文献：
  名称：

  串联分子内逆Diels-Alder反应法合成噻吩并[3,4- ]呋喃

  摘要：

  标题化合物的制备方法涉及以下关键步骤：在呋喃和炔属侧基酯之间进行分子内Diels-Alder加成反应，以及随后由3,6-di（吡啶-2'-基）-四嗪。

  DOI：

  10.1016/s0040-4039(00)84712-7
• 作为产物：
  描述：

  methyl 4-(furan-2'-ylmethylthio)but-2-ynoate 在 copper chromite hydroxide 、 3,6-二-2-吡啶基-1,2,4,5-四嗪 作用下， 以 喹啉 、 甲苯 为溶剂， 反应 18.0h， 生成 4,6-dihydrothieno<3,4-b>furan
  参考文献：
  名称：

  串联分子内逆Diels-Alder反应法合成噻吩并[3,4- ]呋喃

  摘要：

  标题化合物的制备方法涉及以下关键步骤：在呋喃和炔属侧基酯之间进行分子内Diels-Alder加成反应，以及随后由3,6-di（吡啶-2'-基）-四嗪。

  DOI：

  10.1016/s0040-4039(00)84712-7

文献信息

• SYNTHESIS OF THIENO[3,4-b]THIOPHENE, THIENO[3,4-b]FURAN, RELATED COMPOUNDS AND THEIR DERIVATIVES AND USE THEREOF
  申请人：Sotzing Gregory A.

  公开号：US20090326187A1

  公开（公告）日：2009-12-31

  Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.

  揭示了制备噻吩并[3,4-b]噻吩、噻吩并[3,4-b]呋喃、相关化合物及其衍生物的廉价且简便的方法。还揭示了由这些融合杂环制备的规则寡聚物。
• Synthesis of thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds and their derivatives and use thereof
  申请人：The University of Connecticut

  公开号：US08168671B2

  公开（公告）日：2012-05-01

  Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.

  本文揭示了制备融合杂环化合物（如噻吩并[3,4-b]噻吩、噻吩并[3,4-b]呋喃等）及其衍生物的廉价和简便方法。同时还揭示了由这些融合杂环化合物制备的规则构型聚合物。
• A,B-Diheteropentalenes by a Tandem Intramolecular Diels-Alder/Reverse Diels-Alder Reaction Sequence. Application to the Synthesis of Thieno[3,4-b]furan
  作者：JH Buttery、J Moursounidis、D Wege

  DOI：10.1071/ch9950593

  日期：——

  Alkylation of 2-furylmethanethiol (28) with propargyl chloride gave the thioether (22) which on methoxycarbonylation afforded the acetylenic ester (30). On heating, this material underwent an intramolecular Diels -Alder reaction to give the tricyclic compound (32). In the presence of 3,6- di (pyridin-2′-yl)-s- tetrazine , (32) afforded methyl 4,6-dihydrothieno[3,4-b]furan-3-carboxylate (38) by a sequence involving a further Diels -Alder reaction followed by two reverse Diels-Alder reactions. The ester (38) could be dehydrogenated to give methyl thieno [3,4-b]furan-3-carboxylate (40) while hydrolysis of (38), followed by decarboxylation and dehydrogenation delivered the parent thieno [3,4-b]furan (5). 3-Methyl-4,6-dihydrothieno[3,4-b]furan (46) and 3-methylthieno[3,4-b]furan (47) were prepared; a comparison of the 4JMe-C=C-H coupling constants in the 1H n.m.r . spectra of (46) and (47) suggests that an increase in the C2-C3 furyl bond order accompanies the (46) → (47) conversion. Methyl 4,6-dihydrofuro[3,4-b]furan-3-carboxylate (39), 4,6-dihydrofuro[3,4-b]furan (27) and methyl 4,6-dihydro-6-phenylfuro[3,4-b]furan-3-carboxylate (53) were prepared by an analogous tandem reaction sequence. These compounds could not be dehydrogenated to the fully conjugated furo [3,4-b]furan ring system.

  2-呋喃甲硫醇（28）与丙炔酰氯发生烷基化反应，生成硫醚（22），硫醚经甲氧基羰基化反应生成乙炔酯（30）。加热后，这种物质发生分子内 Diels -Alder 反应，生成三环化合物 (32)。在 3,6- di (pyridin-2′-yl)-s- tetrazine 的存在下，(32) 通过进一步的 Diels -Alder 反应和两个反向 Diels-Alder 反应，得到 4,6- 二氢噻吩并[3,4-b]呋喃-3-羧酸甲酯 (38)。酯 (38) 可以通过脱氢反应得到噻吩并[3,4-b]呋喃-3-羧酸甲酯 (40)，而 (38) 经过水解、脱羧和脱氢反应得到母体噻吩并[3,4-b]呋喃 (5)。制备了 3-甲基-4,6-二氢噻吩并[3,4-b]呋喃 (46) 和 3-甲基噻吩并[3,4-b]呋喃 (47)；对 (46) 和 (47) 的 1H n.m.r .光谱中的 4JMe-C=C-H 偶联常数进行比较后发现，在 (46) → (47) 转化过程中，C2-C3 呋喃键的顺序有所增加。4,6- 二氢呋喃并[3,4-b]呋喃-3-羧酸甲酯 (39)、4,6-二氢呋喃并[3,4-b]呋喃 (27) 和 4,6- 二氢-6-苯基呋喃并[3,4-b]呋喃-3-羧酸甲酯 (53) 是通过类似的串联反应顺序制备的。这些化合物无法脱氢成为完全共轭的呋喃 [3,4-b]呋喃环系统。
• US8168671B2
  申请人：——

  公开号：US8168671B2

  公开（公告）日：2012-05-01
• Versatile synthesis of 3,4-b diheteropentalenes
  作者：Tanmoy Dey、Daminda Navarathne、Michael A. Invernale、Ian D. Berghorn、Gregory A. Sotzing

  DOI：10.1016/j.tetlet.2010.02.036

  日期：2010.4

  We describe a new route for the synthesis of thieno[3,4-b]thiophene, alkyl derivatives thereof, seleno[3,4-b]thiophene, and thieno[3,4-b]furan made from inexpensive starting materials, such as thiophene-2-carboxylic acid and furan-2-carboxylic acid. Such fused heterocycles are of great interest for low band gap organic semiconductors and applications including OLEDs, organic photovoltaic cells, and

  我们描述了一种由廉价的起始原料制备的合成噻吩并[3,4- b ]噻吩，其烷基衍生物，硒代[3,4- b ]噻吩和噻吩并[3,4- b ]呋喃的新途径。作为噻吩-2-羧酸和呋喃-2-羧酸。这样的稠合杂环对于低带隙有机半导体以及包括OLED，有机光伏电池和电致变色的应用非常感兴趣。