5,5'-Carbonylbisfuran-2-carbaldehyd | 35050-48-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5'-Carbonylbisfuran-2-carbaldehyd
• 英文别名: 5,5'-carbonyl-bis-furan-2-carbaldehyde；5-(5-Formylfuran-2-carbonyl)furan-2-carbaldehyde
• CAS: 35050-48-7
• 化学式: C₁₁H₆O₅
• 分子量: 218.166
• InChiKey: LVTJNRVQRLIWPN-UHFFFAOYSA-N

物化性质

• 沸点：
  423.9±45.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,5'-Carbonylbisfuran-2-carbaldehyd 在 高氯酸 作用下， 以 乙酸酐 、 三氟乙酸 为溶剂， 生成 dimethyl 3,3'-(5-acetoxy-12,18-dimethyl-21,23-didehydro21,22-dioxaporphyrin-13,17-diyl)dipropionate
  参考文献：
  名称：

  Lash, Timothy B.; Motta, Yanet G., Heterocycles, 1983, vol. 20, # 12, p. 2343 - 2346

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴-2-呋喃甲醛 在 盐酸 、 正丁基锂 、 对甲苯磺酸 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 2.92h， 生成 5,5'-Carbonylbisfuran-2-carbaldehyd
  参考文献：
  名称：

  Lash, Timothy D.; Armiger, Yoek Lin See-Tow, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 965 - 970

  摘要：

  DOI：

文献信息

• Ein erstes Beispiel eines porphyrinoiden Fulvalens: Synthese, Struktur, ESR- und elektrochemische Untersuchungen
  作者：Gottfried Markl、Markus Hafner、Peter Kreitmeier、Christian Stadler、Jörg Daub、Heinrich Nöth、Martin Schmidt、Georg Gescheidt

  DOI：10.1002/hlca.19970800814

  日期：1997.12.15

  A First Example of a Porphyrinoid Fulvalene: Synthesis, Structure, ESR and Electrochemical Investigations

  卟啉类富富瓦烯的第一个实例：合成，结构，ESR和电化学研究
• Annulenoide Tetrathiafulvalene:, 5,16-Bis(1,3-benzodithiol-2-yliden)-5,16-dihydrotetraepoxy- und 5,16-Bis(1,3-benzodithiol-2-yliden)-5,16-dihydrotetraepithio[22]annulene(2.1.2.1)
  作者：Gottfried Märkl、Dirk Bruns、Harald Dietl、Peter Kreitmeier

  DOI：10.1002/1522-2675(20010815)84:8<2220::aid-hlca2220>3.0.co;2-1

  日期：2001.8.15

  The title compounds are among the first tetrathiafulvalenes with annulene spacers, here with tetraepoxy-[22]annulene(2.1.2.1) (see 3a), tetraepithio[22]annulene(2.1.2.1) (see 3b), and diepithiodiepoxy[22]annulene(2.1.2.1) (see 23) units. The annulenoid tetrathiafulvalenes 3a and 3b are prepared by cyclizing McMurry coupling of the 5,5'-(1,3-benzodithiol-2-ylidenemethylene)bis[furan- or thiophene-2-carbaldehydes] (8a or 8b, resp.) or by Wittig reaction of (1,3-benzodithiol-2-yl)tributylphosphonium tetra fluoroborate (13b) with tetraepoxy[22]annulene(2.1.2.1)-1,12-dione 20 (formation of 3a) or diepithiodiepoxy[22]annulene(2.1.2.1)1,12-dione 22 (formation of 23). The annulenoide tetrathiafulvalene 3a is obtained as a mixture of the isomers (E,E)- and (Z,Z)-3a. At 130 degrees, (Z,Z)-3a rearranges quantitatively into the (E,E)-isomer. Isomer (E,E)-3a is a dynamic molecule, where the (E)-ethene-1,2-diyl bridges rotate around the adjacent sigma -bonds, The tetraepithioannulene derivative 3b as well as 23 only exist in the (Z,Z) -configuration. The oxidation of (E,E/Z,Z)-3a with Br-2 yields the annulene -bridged tetrathiafulvalene dication (E,E)-3a(Ox), while with 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (DDQ) obviously only the radical cation 3a(Sem) is formed, which belongs to the class of cyanine-like violenes. The annulenoide tetrathiafulvalenes 3b and 23, which exist only in the (Z,Z) -configuration, obviously for steric reasons, cannot be oxidized by DDQ. Electrochemical studies are in agreement with these results.
• Maerkel, Gottfried; Striebl, Ulrich, Angewandte Chemie, 1993, vol. 105, # 9, p. 1387 - 1390
  作者：Maerkel, Gottfried、Striebl, Ulrich

  DOI：——

  日期：——
• Rusch, Roland; Gast, Achim; Breitmaier, Eberhard, Liebigs Annalen der Chemie, 1990, # 11, p. 1157 - 1159
  作者：Rusch, Roland、Gast, Achim、Breitmaier, Eberhard

  DOI：——

  日期：——
• Tetraoxa-[26]annulenochinon
  作者：Gottfried Märkl、Ulrich Striebl、Peter Kreitmeirer、Andreas Knorr、Michael Porsch、Jörg Daub

  DOI：10.1016/0040-4039(95)00814-s

  日期：1995.6

  The title compound and its electrochemically prepared dianion may be considered as the largest known macrocyclic quinone/hydroquinone-system.