4,7,14,17-tetramethyl-anti-[2.2](1,4)naphthalenophane

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,7,14,17-tetramethyl-anti-[2.2](1,4)naphthalenophane
• 英文别名: 6,9,16,19-Tetramethylpentacyclo[12.6.2.24,11.05,10.015,20]tetracosa-1(21),4(24),5,7,9,11(23),14(22),15,17,19-decaene
• 化学式: C₂₈H₂₈
• 分子量: 364.53
• InChiKey: AWTBHNKJOXURLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  4,5,12,13-tetrabromo[2.2]paracyclophane 在 lithium aluminium tetrahydride 、 正丁基锂 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 4,7,14,17-tetramethyl-anti-[2.2](1,4)naphthalenophane
  参考文献：
  名称：

  Synthesis of Substituted Dibenzoequinenes

  摘要：

  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.

  DOI：

  10.1021/jo9708351

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.