(E,E,E)-5,5'-(Hexa-1,3,5-trien-1,6-diyl)bis | 180135-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,E,E)-5,5'-(Hexa-1,3,5-trien-1,6-diyl)bis
• 英文别名: (all-E)-5,5-(hexa-1,3,5-trien-1,6-diyl)bis[furan-2-carboxaldehyd]；5-[(1E,3E,5E)-6-(5-formylfuran-2-yl)hexa-1,3,5-trienyl]furan-2-carbaldehyde
• CAS: 180135-66-4
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: LTPLAVYBGUHNHQ-CRQXNEITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,E,E)-5,5'-(Hexa-1,3,5-trien-1,6-diyl)bis 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以99.9%的产率得到(E,E,E)-5,5'-(Hexa-1,3,5-trien-1,6-diyl)bis
  参考文献：
  名称：

  Konfigurations- und konformationsisomere paratrope, rotationsdynamische Tetraepoxy[32]annulene(6.2.6.2) und diatrope Tetraoxa[30]porphyrin(6.2.6.2)-Dikationen: Nachweis eines Tetraepoxy[31]annulen(6.2.6.2)-Radikalkations

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19990113)82:1<59::aid-hlca59>3.0.co;2-8
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 (1E,3E,5E)-1,6-bis(2-furyl)hexa-1,3,5-triene 在 三氯氧磷 作用下， 以87%的产率得到(E,E,E)-5,5'-(Hexa-1,3,5-trien-1,6-diyl)bis
  参考文献：
  名称：

  Konfigurations- und konformationsisomere paratrope, rotationsdynamische Tetraepoxy[32]annulene(6.2.6.2) und diatrope Tetraoxa[30]porphyrin(6.2.6.2)-Dikationen: Nachweis eines Tetraepoxy[31]annulen(6.2.6.2)-Radikalkations

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19990113)82:1<59::aid-hlca59>3.0.co;2-8

文献信息

• Superheteroaromaten mit Furan-Bausteinen: Isomere antiaromatische Tetraepoxy[36]annulene(6.4.6.4) und aromatische Tetraoxa[34]porphyrin(6.4.6.4)-Dikationen
  作者：Gottfried Märkl、Robert Ehrl、Peter Kreitmeier、Thomas Burgemeister

  DOI：10.1002/(sici)1522-2675(20000216)83:2<495::aid-hlca495>3.0.co;2-3

  日期：2000.2.16

  The title compounds are available by a twofold cyclizing Wittig reaction of (all-E)-3,3'-(hexa-1,3,5-triene-1,6-diyldifuran-5,2-diyl)bis[prop-2-enal] (4) with (all-E)-(hexa-1,3,5-triene-1,6-diyl)bis(furan-5,2-diylmethylene)-bis[triphenylphosphonium] dibromide (7). Two conformational isomers 2a/2a' of (Z,E,E,E,E,Z,E,E,E,E)-tetraepoxy[36]annulene (6.4.6.4) are obtained. The oxidation of 2a/2a' yields two (E,E,Z, E,E,E,E,Z,E,E)-tetraoxa[34]porphyrin(6.4.6.4) dications 3a/3a', which are conformers, too. The oxidation of 2a/2a' is accompanied by the isomerization of four ethen-1,2-diyl bridges. The reduction of the dications 3a/3a' leads to the new (E,E,Z,E,E,E,E,Z,E,E)-tetraepoxy[36]ann (2b) and (E,E,E,Z,E,E,E,E,Z,E)-tetraepoxy[36]annulene(6.4.6.4) (2c). In 2b as well as in 2c, both 1,3-butadiene-1,4-diyl bridges are rotating until -90 degrees. The Delta delta values, ie., the maximum delta difference of the 'inner' and 'outer' perimeter protons of 3a/3a' (26.62 and 25.32 ppm) are of the same size as the Delta delta value of the tetramethyl[34]porphyrin(5.5.5.5) dication (1; Delta delta = 25.3 ppm); therefore, they might be called 'superheteroaromatic' too. The Delta delta values of the tetraepoxy[36]annulenes(6.4.6.4) (2a-c; Delta delta = 2.3-3.3 ppm) establish that they are still paratropic; they represent the most expanded antiaromatic systems yet known.
• Konfigurations- und konformationsisomere paratrope, rotationsdynamische Tetraepoxy[32]annulene(6.2.6.2) und diatrope Tetraoxa[30]porphyrin(6.2.6.2)-Dikationen: Nachweis eines Tetraepoxy[31]annulen(6.2.6.2)-Radikalkations
  作者：Gottfried Märkl、Robert Ehrl、Heinrich Sauer、Peter Kreitmeier、Thomas Burgemeister

  DOI：10.1002/(sici)1522-2675(19990113)82:1<59::aid-hlca59>3.0.co;2-8

  日期：1999.1.13