1,5-Bis(trans-β-carbethoxyethenyl)naphthalene | 152873-87-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,5-Bis(trans-β-carbethoxyethenyl)naphthalene
• 英文别名: ethyl (E)-3-[5-[(E)-3-ethoxy-3-oxoprop-1-enyl]naphthalen-1-yl]prop-2-enoate
• CAS: 152873-87-5
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: SDUBKDQIGKCEBZ-PHEQNACWSA-N

物化性质

• 沸点：
  492.8±25.0 °C(predicted)
• 密度：
  1.164±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-Bis(trans-β-carbethoxyethenyl)naphthalene 以 苯 为溶剂， 反应 6.0h， 以47%的产率得到tetraethyl (2S,3R,4S,5R,16R,17S,18R,19S)-heptacyclo[22.4.0.02,5.06,11.010,15.016,19.020,25]octacosa-1(28),6,8,10,12,14,20,22,24,26-decaene-3,4,17,18-tetracarboxylate
  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：

  1,5-二羟基萘 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.08h， 生成 1,5-Bis(trans-β-carbethoxyethenyl)naphthalene
  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.