3,4,13,14-Tetraphenylheptacyclo<14.4.4.4^6,11.0^2,5.0^7,28.0^12,15.0^17,21>-octacosa-1(20),6(25),7(28),8,10,16(24),17(21),18,22,26-decaen | 121373-47-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 英文名称: 3,4,13,14-Tetraphenylheptacyclo<14.4.4.4^6,11.0^2,5.0^7,28.0^12,15.0^17,21>-octacosa-1(20),6(25),7(28),8,10,16(24),17(21),18,22,26-decaen
• 英文别名: (2R,3S,4R,5S,16S,17R,18S,19R)-3,4,17,18-tetraphenylheptacyclo[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
• CAS: 121373-47-5
• 化学式: C₅₂H₄₀
• 分子量: 664.89
• InChiKey: YGZQXUUYRGKBPD-BYLOPRMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  52
• 可旋转键数：
  4
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 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 、 苯 为溶剂， 反应 54.08h， 生成 3,4,13,14-Tetraphenylheptacyclo<14.4.4.4^6,11.0^2,5.0^7,28.0^12,15.0^17,21>-octacosa-1(20),6(25),7(28),8,10,16(24),17(21),18,22,26-decaen
  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

• Meier, Herbert; Prass, Ellen; Zertani, Rudolf, Chemische Berichte, 1989, vol. 122, p. 2139 - 2147
  作者：Meier, Herbert、Prass, Ellen、Zertani, Rudolf、Eckes, Heinz-Ludwig

  DOI：——

  日期：——
• [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.