(E,E)-2,5-bis[2,5-(diallyloxy)styryl]-1,4-dihexylbenzene | 493036-94-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E)-2,5-bis[2,5-(diallyloxy)styryl]-1,4-dihexylbenzene
• 英文别名: 1,4-bis[(E)-2-[2,5-bis(prop-2-enoxy)phenyl]ethenyl]-2,5-dihexylbenzene
• CAS: 493036-94-5
• 化学式: C₄₆H₅₈O₄
• 分子量: 674.964
• InChiKey: SFVHQDLIHHBJGQ-MBALSZOMSA-N

物化性质

• 沸点：
  767.6±48.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  50
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,E)-2,5-bis[2,5-(diallyloxy)styryl]-1,4-dihexylbenzene 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 54.0h， 生成 2-[(E)-2-{4-[(E)-2-(2,5-dioxocyclohexa-1,3-dien-1-yl)ethenyl]-2,5-dihexylphenyl}ethenyl]-1,4-benzoquinone
  参考文献：
  名称：

  1,4-Benzoquinones with Styryl Substituents

  摘要：

  2-Styryl-1,4-benzoquinone (1) and compounds 2 and 3 containing 1 as a substructure all proved to be highly reactive towards thermal or photochemical [4pi + 2pi] cyclodimerization reactions. Chemo-, regio- and stereoselective processes lead to dimers (compounds 1-10), which can undergo secondary reactions consisting of the addition of nucleophiles combined with a twofold keto-enol tautomerism (10 --> 12). An alternative process is dehydrogenation/oxidation followed by an intramolecular [4pi + 2pi] cycloaddition (10 --> 11). The same selective [4pi + 2pi] cyclodimerization can be observed in solution upon irradiation (e.g., 1a --> 10a), in contrast to irradiation in the crystalline state which yields a [2pi + 2pi] dimer (e.g., 1a --> 13). If more than one styrylbenzoquinone moiety is present in the same molecule the oligomers 2a (n = 1-3) and 3a (n = 1-4) are obtained. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200209)2002:18<3162::aid-ejoc3162>3.0.co;2-h
• 作为产物：
  描述：

  2,5-bis(bromomethyl)-1,4-dihexylbenzene 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 9.0h， 生成 (E,E)-2,5-bis[2,5-(diallyloxy)styryl]-1,4-dihexylbenzene
  参考文献：
  名称：

  1,4-Benzoquinones with Styryl Substituents

  摘要：

  2-Styryl-1,4-benzoquinone (1) and compounds 2 and 3 containing 1 as a substructure all proved to be highly reactive towards thermal or photochemical [4pi + 2pi] cyclodimerization reactions. Chemo-, regio- and stereoselective processes lead to dimers (compounds 1-10), which can undergo secondary reactions consisting of the addition of nucleophiles combined with a twofold keto-enol tautomerism (10 --> 12). An alternative process is dehydrogenation/oxidation followed by an intramolecular [4pi + 2pi] cycloaddition (10 --> 11). The same selective [4pi + 2pi] cyclodimerization can be observed in solution upon irradiation (e.g., 1a --> 10a), in contrast to irradiation in the crystalline state which yields a [2pi + 2pi] dimer (e.g., 1a --> 13). If more than one styrylbenzoquinone moiety is present in the same molecule the oligomers 2a (n = 1-3) and 3a (n = 1-4) are obtained. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200209)2002:18<3162::aid-ejoc3162>3.0.co;2-h

文献信息

• 1,4-Benzoquinones with Styryl Substituents
  作者：Isabella Brehm、Sabine Hinneschiedt、Herbert Meier

  DOI：10.1002/1099-0690(200209)2002:18<3162::aid-ejoc3162>3.0.co;2-h

  日期：2002.9

  2-Styryl-1,4-benzoquinone (1) and compounds 2 and 3 containing 1 as a substructure all proved to be highly reactive towards thermal or photochemical [4pi + 2pi] cyclodimerization reactions. Chemo-, regio- and stereoselective processes lead to dimers (compounds 1-10), which can undergo secondary reactions consisting of the addition of nucleophiles combined with a twofold keto-enol tautomerism (10 --> 12). An alternative process is dehydrogenation/oxidation followed by an intramolecular [4pi + 2pi] cycloaddition (10 --> 11). The same selective [4pi + 2pi] cyclodimerization can be observed in solution upon irradiation (e.g., 1a --> 10a), in contrast to irradiation in the crystalline state which yields a [2pi + 2pi] dimer (e.g., 1a --> 13). If more than one styrylbenzoquinone moiety is present in the same molecule the oligomers 2a (n = 1-3) and 3a (n = 1-4) are obtained. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).