syn-<2,2>(1,4)-5,8-Naphthochinonophan | 204401-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: syn-<2,2>(1,4)-5,8-Naphthochinonophan
• 英文别名: anti-<2,2>(1,4)-5,8-Naphthochinonophan；Pentacyclo[12.6.2.24,11.05,10.015,20]tetracosa-1(20),4,7,10,14,17,21,23-octaene-6,9,16,19-tetrone
• CAS: 204401-79-6
• 化学式: C₂₄H₁₆O₄
• 分子量: 368.389
• InChiKey: ZPIXONMQAYNFKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  syn-<2,2>(1,4)-5,8-Naphthochinonophan 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  Staab,H.A.; Herz,C.P., Angewandte Chemie, 1977, vol. 89, p. 406 - 407

  摘要：

  DOI：
• 作为产物：
  描述：

  syn-4,7,14,17-Tetramethoxy-<2,2>(1,4)-naphthalinophan 生成 syn-<2,2>(1,4)-5,8-Naphthochinonophan
  参考文献：
  名称：

  Staab,H.A.; Herz,C.P., Angewandte Chemie, 1977, vol. 89, p. 406 - 407

  摘要：

  DOI：

文献信息

• Synthesis of Substituted Dibenzoequinenes
  作者：Rolf Gleiter、Katrin Staub、Hermann Irngartinger、Thomas Oeser

  DOI：10.1021/jo9708351

  日期：1997.10.1

  The naphthalenophanes with four donor groups such as 4,7,14,17-tetramethoxy-anti-[2.2](1,4)naphthalenophane (10), the corresponding syn-isomer 10a, and 4,7,14,17-tetramethy1-anti-[2.2](1,4)naphthalenophane (17) together with the naphthalenophanes with four acceptor groups, 4,7,14,17-tetracyano-anti-[2,2](1,4)naphthalenophane (21), and 5,6,15,16-tetracarbethoxy-anti-[2.2](1,4)naphthalenophane (23), belonging to point group C-2h for the anti-and C-2v for the syn-isomer, have been synthesized following mostly known procedures. Furthermore, the preparation of 5,6-dicarbethoxynaphthaleno-[2.2](1,4)naphthalenophane (27) and 2,5-dimethoxynaphthaleno-anti-[2.2](1,4)-5,8-naphthochinonophane (28) with one donor and one acceptor substituted ring supplements the series. The irradiation of 10, 21, 23, and 27 yields 2,2',5,5'-tetramethoxydibenzoequinene (30), 2,2',5,5'-tetracyanodibenzoequinene (31), 3,3',4,4'-tetracarbethsxydibenzoequinene (32) and 3,4-dicarbethoxydibenzoequinene (33). Structural investigations on 30 by means ofthe X-ray method show a strong folding of the cyclobutane rings. The average bond length of the four-membered rings in 30 was found to be 1.579(2) Angstrom. The values obtained for the bond lengths and bond angles resemble those of the parent system 2. Long ethano bonds (1.556-1.591 Angstrom) in the bridges were found in the synand anti-naphthalenophanes 10a, 14, and 17 by means ofX-ray structure analysis.