[Carbonylbis(furan-5,2-diyl)]bisphosphonium-dichlorid | 37893-23-5

• 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: [Carbonylbis(furan-5,2-diyl)]bisphosphonium-dichlorid
• 英文别名: hexa-P-phenyl-P,P'-(5,5'-carbonyl-bis-furan-2-ylmethyl)-bis-phosphonium; dichloride
• CAS: 37893-23-5
• 化学式: C₄₇H₃₈O₃P₂*2Cl
• 分子量: 783.67
• InChiKey: IARQQKIQZJWXOJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  53.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  43.35
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [Carbonylbis(furan-5,2-diyl)]bisphosphonium-dichlorid 在 lithium aluminium tetrahydride 、 三氯化铝 、 lithium methanolate 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 61H-1,3(2,5)-difurana-6(2,5)-pyrrola-cyclooctaphane-4c,7c-diene
  参考文献：
  名称：

  Cresp,T.M.; Sargent,M.V., Journal of the Chemical Society. Perkin transactions I, 1973, p. 2961 - 2971

  摘要：

  DOI：
• 作为产物：
  描述：

  三苯基膦 、 Bis-(5-chloromethyl-furan-2-yl)-methanone 以90%的产率得到[Carbonylbis(furan-5,2-diyl)]bisphosphonium-dichlorid
  参考文献：
  名称：

  Maerkel, Gottfried; Striebl, Ulrich, Angewandte Chemie, 1993, vol. 105, # 9, p. 1387 - 1390

  摘要：

  DOI：

文献信息

• 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.