1,7-Divinylnaphthalene | 152873-84-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,7-Divinylnaphthalene
• 英文别名: 1,7-Bis(ethenyl)naphthalene
• CAS: 152873-84-2
• 化学式: C₁₄H₁₂
• 分子量: 180.249
• InChiKey: BOLTUABUSJWLJP-UHFFFAOYSA-N

物化性质

• 沸点：
  315.9±12.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,7-Divinylnaphthalene 以 苯 为溶剂， 反应 6.0h， 生成 exo,endo,syn-<2.2>(1,7)-Naphthalenophane 、 exo,exo,syn-<2.2>(1,7)-Naphthalenophane
  参考文献：
  名称：

  [2.2]Naphthalenophanes from intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes

  摘要：

  syn-[2.2]Naphthalenophanes were obtained exclusively in reasonable yields from the intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes. The position of the vinyl group and the type of vinyl substituent affected the isomer ratio of the products. The structures of naphthalenophanes were elucidated by H-1-NMR spectroscopy including COSY and NOESY experiments. Among the divinylnaphthalenes examined, 1,4-, 1,5-, and 1,6-ones did not give the desired naphthalenophanes. By taking advantage of the effect of the substituents on the photoreaction, we could obtain [2.2]-(1,5)naphthalenophane derivatives from 1,5-bis(beta-carbethoxyethenyl)naphthalene and 1,5-bis(beta-phenylethenyl)naphthalene, but we could not obtain the 1,4-isomers, probably because they are highly strained. Although a mixture of two different divinylnaphthalenes was irradiated, only homo-adducts were obtained; no cross adducts were detected.

  DOI：

  10.1021/jo00078a016
• 作为产物：
  描述：

  1,7-二羟基萘 在 四(三苯基膦)钯 吡啶 、 对叔丁基邻苯二酚 、 lithium chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 28.08h， 生成 1,7-Divinylnaphthalene
  参考文献：
  名称：

  [2.2]Naphthalenophanes from intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes

  摘要：

  syn-[2.2]Naphthalenophanes were obtained exclusively in reasonable yields from the intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes. The position of the vinyl group and the type of vinyl substituent affected the isomer ratio of the products. The structures of naphthalenophanes were elucidated by H-1-NMR spectroscopy including COSY and NOESY experiments. Among the divinylnaphthalenes examined, 1,4-, 1,5-, and 1,6-ones did not give the desired naphthalenophanes. By taking advantage of the effect of the substituents on the photoreaction, we could obtain [2.2]-(1,5)naphthalenophane derivatives from 1,5-bis(beta-carbethoxyethenyl)naphthalene and 1,5-bis(beta-phenylethenyl)naphthalene, but we could not obtain the 1,4-isomers, probably because they are highly strained. Although a mixture of two different divinylnaphthalenes was irradiated, only homo-adducts were obtained; no cross adducts were detected.

  DOI：

  10.1021/jo00078a016

文献信息

• [2.2]Naphthalenophanes from intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes
  作者：Motoharu Takeuchi、Takeshi Tuihiji、J. Nishimura

  DOI：10.1021/jo00078a016

  日期：1993.12

  syn-[2.2]Naphthalenophanes were obtained exclusively in reasonable yields from the intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes. The position of the vinyl group and the type of vinyl substituent affected the isomer ratio of the products. The structures of naphthalenophanes were elucidated by H-1-NMR spectroscopy including COSY and NOESY experiments. Among the divinylnaphthalenes examined, 1,4-, 1,5-, and 1,6-ones did not give the desired naphthalenophanes. By taking advantage of the effect of the substituents on the photoreaction, we could obtain [2.2]-(1,5)naphthalenophane derivatives from 1,5-bis(beta-carbethoxyethenyl)naphthalene and 1,5-bis(beta-phenylethenyl)naphthalene, but we could not obtain the 1,4-isomers, probably because they are highly strained. Although a mixture of two different divinylnaphthalenes was irradiated, only homo-adducts were obtained; no cross adducts were detected.