5,12-Dimethoxy-1,4,7,10-hexahydro-1,4:7,10-dimethanonaphthacene | 154875-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,12-Dimethoxy-1,4,7,10-hexahydro-1,4:7,10-dimethanonaphthacene
• 英文别名: (1S,7R,10S,16R)-3,14-dimethoxyhexacyclo[14.2.1.17,10.02,15.04,13.06,11]icosa-2,4,6(11),8,12,14,17-heptaene
• CAS: 154875-43-1
• 化学式: C₂₂H₂₀O₂
• 分子量: 316.4
• InChiKey: GHHQVDSTQZCALL-LVEBTZEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,12-Dimethoxy-1,4,7,10-hexahydro-1,4:7,10-dimethanonaphthacene 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 120.0h， 生成 7,8-Dimethoxy-1,2,3,4,5,5a,6,9,9a,10,11,12,13,14,15,15a,16,19,19a,20-eicosahydro-2,3,12,13-tetramethylene-1,4:6,19:9,16:11,14-tetramethanooctacene
  参考文献：
  名称：

  通过使用压力诱导的重复Diels-Alder反应合成空间刚性大环

  摘要：

  所述的合成顺式-dimethanotetrahydroanthracene和-tetracene衍生物2A - d和图6a，b进行了描述。这些双-亲二烯体与双-二烯7的高度立体选择性，压力诱导的重复Diels-Alder反应导致空间刚性大环10a，10d，13a和14a，b具有明确定义的不同大小的腔。

  DOI：

  10.1016/0040-4039(94)88165-0
• 作为产物：
  描述：

  (1S,4S)-2-bromo-5,6-dimethylenebicyclo[2.2.1]hept-2-ene 以 甲苯 为溶剂， 反应 96.0h， 生成 5,12-Dimethoxy-1,4,7,10-hexahydro-1,4:7,10-dimethanonaphthacene
  参考文献：
  名称：

  通过使用压力诱导的重复Diels-Alder反应合成空间刚性大环

  摘要：

  所述的合成顺式-dimethanotetrahydroanthracene和-tetracene衍生物2A - d和图6a，b进行了描述。这些双-亲二烯体与双-二烯7的高度立体选择性，压力诱导的重复Diels-Alder反应导致空间刚性大环10a，10d，13a和14a，b具有明确定义的不同大小的腔。

  DOI：

  10.1016/0040-4039(94)88165-0

文献信息

• Synthesis of Sterically Rigid Macrocycles by The Use of Pressure-Induced Repetitive Diels–Alder Reactions
  作者：Johannes Benkhoff、Roland Boese、Frank-Gerrit Klärner

  DOI：10.1002/jlac.199719970310

  日期：1997.3

  syn-dimethanotetrahydroanthracene, -tetracene, and -pentacene derivatives 8a–d, 9a–d, and syn-25 are described. Highly stereoselective, pressure-induced Diels-Alder reactions of the bis-dienophiles 8a and/or 9a with the bis-diene 7 lead to the sterically rigid macrocycles 1a, 2a, and 3a/3b, which have well defined cavities of different sizes.

  描述了顺-二甲氨基四氢蒽，-并四苯和-并五苯衍生物8a-d，9a-d和syn - 25的合成。双亲二烯体8a和/或9a与双二烯7的高度立体选择性的，压力诱导的Diels-Alder反应导致空间刚性大环1a，2a和3a / 3b，其具有明确定义的不同大小的腔。
• Klaerner, Frank-Gerrit; Benkhoff, Johannes; Boese, Roland, Angewandte Chemie, 1996, vol. 108, # 10, p. 1195 - 1198
  作者：Klaerner, Frank-Gerrit、Benkhoff, Johannes、Boese, Roland、Burkert, Ulrich、Kamieth, Markus、Naatz, Ulf

  DOI：——

  日期：——
• Molecular tweezers as synthetic receptors: molecular recognition of neutral and cationic aromatic substrates. A comparison between the supramolecular structures in crystal and in solution
  作者：Frank-Gerrit Kl�rner、Ulrich Burkert、Markus Kamieth、Roland Boese

  DOI：10.1002/1099-1395(200010)13:10<604::aid-poc271>3.0.co;2-7

  日期：2000.10

  The synthesis of substituted naphthalene- and benzene-spaced tweezer molecules Ib and c and 2e-j is reported. They selectively bind electron-deficient neutral and cationic aromatic substrates. The structural parameters of the substrate-receptor complexes derived from H-1 NMR measurements in solution are in good agreement with those obtained from single-crystal structure analyses. The tweezer 2f forms a stable complex with N,N-bis-(3,5-di-tert-butylbenzyl)-4,4'-bipyridinium 14, a substituted viologen dication, that exhibits the structure of a clipped rotaxane with a wheel opened on one side. The benzene-spaced tweezer 2j shows complexation of the cesium cation Cri inside the cavity. Copyright (C) 2000 John Wiley & Sons, Ltd.
• Bis-corannulene Receptors for Fullerenes Based on Klärner’s Tethers: Reaching the Affinity Limits
  作者：Peumie L. Abeyratne Kuragama、Frank R. Fronczek、Andrzej Sygula

  DOI：10.1021/acs.orglett.5b02666

  日期：2015.11.6

  Bis-corannulene receptors 4 and 5 with Khmer's tethers prepared by the Diels-Alder cycloaddition form inclusion complexes with C-60 and C-70, as evidenced by H-1 NMR titration. While 4 exhibits affinity toward fullerenes comparable to the previously reported corannulene-based receptors, 5 exceeds the performance of the former systems by ca. 2 orders of magnitude and, in addition, shows an enhanced preference for C-70 over C-60. The X-ray crystal structure of C-60@5 and DFT calculations indicate that the tether in 5 not only preorganizes the pincers into a proper topology of the host but also contributes to the dispersion-based binding with the fullerene guests.