5,12-Diacetoxy-1,4,7,10-tetrahydro-1,4:7,10-dimethanonaphthacene | 189133-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,12-Diacetoxy-1,4,7,10-tetrahydro-1,4:7,10-dimethanonaphthacene
• 英文别名: [(1S,7R,10S,16R)-14-acetyloxy-3-hexacyclo[14.2.1.17,10.02,15.04,13.06,11]icosa-2,4,6(11),8,12,14,17-heptaenyl] acetate
• CAS: 189133-04-8
• 化学式: C₂₄H₂₀O₄
• 分子量: 372.42
• InChiKey: VDVVRRVQJUFXIK-SYMSYNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5,12-Diacetoxy-1,4,7,10-tetrahydro-1,4:7,10-dimethanonaphthacene 在 氢氧化钾 、 18-冠醚-6 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以87%的产率得到[(1S,7R,10S,16R)-14-hydroxy-3-hexacyclo[14.2.1.17,10.02,15.04,13.06,11]icosa-2,4,6(11),8,12,14,17-heptaenyl] acetate
  参考文献：
  名称：

  取代基对芳香族和醌类底物与分子镊子和夹子络合的影响

  摘要：

  在中心间隔单元中被 OAc、OH、OCONHPh、OMe、OCH2COOR 和 OCH2CONHR 基团取代的 1-3 型分子镊子和夹子已通过标准方法通过修饰合成，已知的双乙酰氧基取代衍生物 1b、2b 和3b，或相应取代的双亲二烯体 4b 和 5b。二甲氧基-双乙酰氧基取代的镊子 1d 的合成可以通过压力诱导的双亲二烯体 4b 和新制备的二烯 6b 之间的重复 Diels-Alder 反应以及随后的 DDQ 氧化来完成。新受体与芳香族底物如 DCNB 21、TCNB 22、TCNQ 24 和 Kosower salt 25 之间形成复合物的热力学参数（Ka 和 ΔG）以及最大络合诱导的 1H NMR 位移（Δδmax.）由 1H NMR 确定滴定实验。发现在镊子和夹子 1-3 的中央间隔单元中存在取代基 OH、OAc 和 OCONHPh 有利于复合物的形成，而取代基 OMe、OCH2COOR

  DOI：

  10.1002/ejoc.200300704

文献信息

• Synthesis and supramolecular structures of molecular clips
  作者：Frank-Gerrit Klärner、Jens Panitzky、Dieter Bläser、Roland Boese

  DOI：10.1016/s0040-4020(01)00230-7

  日期：2001.4

  The syntheses of the novel dimethylene-bridged clips 4a-e and 5b are reported. They selectively bind electron-deficient neutral and cationic aromatic substrates comparable to the tetramethylene-bridged tweezers 1 and 2. The geometry of the noncovalently bound complexes with 4b-d as receptors derived from the single-crystal structure analyses is, however, different from that of the complexes with 2 as receptor. In clip complexes the plane of the included aromatic substrate molecule is orientated almost parallel to the naphthalene sidewalls of the clip, whereas in the tweezer complex the substrate is orientated parallel to the central arene spacer-unit. TCNB 19 as substrate is placed inside the cavity of the hydroquinone clip 4c in solution as well as in the cocrystal. In contrast it was found for the cocrystal with the diacetate clip 4b that the TCNB 19, is placed between the naphthalene side-wall of two different clip molecules whereas in solution 19 is included into the cavity of 4b. Finally, 19 forms a (1:2) complex with dinaphthonorbornadiene 20 in solution as well as in the crystalline state. The findings reported here are instructive for the understanding of the weak; noncovalent binding forces particularly the arene-arene interaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.