(all-E)-3,3'-(hexa-1,3,5-trien-1,6-diylfuran-5,2-diyl)bis[prop-2-enal] | 265670-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (all-E)-3,3'-(hexa-1,3,5-trien-1,6-diylfuran-5,2-diyl)bis[prop-2-enal]
• 英文别名: 2-Propenal, 3,3a(2)-[(1E,3E,5E)-1,3,5-hexatriene-1,6-diyldi-5,2-furandiyl]bis-, (2E,2a(2)E)-；(E)-3-[5-[(1E,3E,5E)-6-[5-[(E)-3-oxoprop-1-enyl]furan-2-yl]hexa-1,3,5-trienyl]furan-2-yl]prop-2-enal
• CAS: 265670-81-3
• 化学式: C₂₀H₁₆O₄
• 分子量: 320.345
• InChiKey: FLMYFBLARYLYQG-OHENXXMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (all-E)-3,3'-(hexa-1,3,5-trien-1,6-diylfuran-5,2-diyl)bis[prop-2-enal] 在 lithium methanolate 、 溴 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.33h， 生成
  参考文献：
  名称：

  Superheteroaromaten mit Furan-Bausteinen: Isomere antiaromatische Tetraepoxy[36]annulene(6.4.6.4) und aromatische Tetraoxa[34]porphyrin(6.4.6.4)-Dikationen

  摘要：

  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.

  DOI：

  10.1002/(sici)1522-2675(20000216)83:2<495::aid-hlca495>3.0.co;2-3
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以0.61 g的产率得到(all-E)-3,3'-(hexa-1,3,5-trien-1,6-diylfuran-5,2-diyl)bis[prop-2-enal]
  参考文献：
  名称：

  Superheteroaromaten mit Furan-Bausteinen: Isomere antiaromatische Tetraepoxy[36]annulene(6.4.6.4) und aromatische Tetraoxa[34]porphyrin(6.4.6.4)-Dikationen

  摘要：

  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.

  DOI：

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