9,10-dihydroxy-1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydroanthracene | 155612-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 9,10-dihydroxy-1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydroanthracene
• 英文别名: 1,2,3,4,5,6,7,8-octahydro-1,4;5,8-dimethano-anthracene-9,10-diol；9.10-Dioxy-1.4;5.8-dimethylen-1.2.3.4.5.6.7.8-oktahydro-anthracen；1,2,3,4,5,6,7,8-Octahydro-1,4;5,8-dimethano-anthracen-9,10-diol；1.4;5.8-Dimethylen-1.2.3.4.5.6.7.8-oktahydro-anthrahydrochinon；1,2,3,4,5,6,7,8-Octahydro-1,4:5,8-dimethanoanthracene-9,10-diol；pentacyclo[10.2.1.15,8.02,11.04,9]hexadeca-2,4(9),10-triene-3,10-diol
• CAS: 155612-44-5
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: DFNCYTRBFWCVOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,10-dihydroxy-1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydroanthracene 在 sodium ethanolate 、 二氧化氮 作用下， 以 二氯甲烷 为溶剂， 反应 12.41h， 生成 1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydro-9,10-anthraquinone
  参考文献：
  名称：

  Rathore, Rajendra; Bosch, Eric; Kochi, Jay K., Journal of the Chemical Society. Perkin transactions II, 1994, # 6, p. 1157 - 1166

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊二烯-苯醌 (2:1) 加合物 在 palladium on activated charcoal 氢气 、 溴 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 6.0h， 生成 9,10-dihydroxy-1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydroanthracene
  参考文献：
  名称：

  Isolation of Novel Radical Cations from Hydroquinone Ethers. Conformational Transition of the Methoxy Group upon Electron Transfer

  摘要：

  Hydroquinone ethers as the bis-annulated derivatives R1-R3 are excellent electron donors by virtue of the facile oxidation to their radical cations R1(.+), R2(.-), and R3(.-) that are readily isolable as unusually robust SbCl6- and BF4- salts persistent in air for prolonged periods. Although the gas-phase vertical ionization potentials of the methyl ethers R1a and R2a are the same (IP = 7.83 +/- 0.01 eV), the oxidation potential of R1a in dichloromethane solution is less positive than that of R2a (E(1/2) = 1.11 and 1.30 V, respectively). The significantly lower value of E(1/2) for R1a relative to R2a, despite minimal changes in structure, is attributed to the conformational change that can occur in the radical cation. Indeed, X-ray crystallographic analysis of R1a, R2a, and R1a(.-) shows that the increased donor strength of R1a is derived from the enhanced (resonance) stabilization of R1a(.-), in which the methoxy group undergoes a 90 degrees rotation to the favorable coplanar conformation with respect to the aromatic ring. The subtle variation in the molecular structures of R1 and R2 accounts for the difference in nonbonded steric effects arising from the bridgehead alpha-hydrogens toward the methoxy groups.

  DOI：

  10.1021/jo00119a017

文献信息

• Chiroptical Properties of Organic Radical Cations. The Electronic and Vibrational Circular Dichroism Spectra of α-Tocopherol Derivatives and Sterically Hindered Chiral Hydroquinone Ethers
  作者：Tadashi Mori、Hiroshi Izumi、Yoshihisa Inoue

  DOI：10.1021/jp0463520

  日期：2004.11.1

  examine the chiroptical properties of organic radical cations and also compare them with those of the corresponding neutral compounds. The observed VCD spectra of neutral and radical cationic species of chiral hydroquinone ether were nicely simulated by density functional theory (DFT) calculations, from which the relative contribution of each radical cation conformer in solution was evaluated. Thus, the combined

  首次用α-生育酚衍生物和空间位阻手性氢醌醚获得了手性有机自由基阳离子的定性和定量可靠的电子和振动圆二色谱（ECD和VCD）光谱。手性自由基阳离子盐的分离和光谱测量是通过使用亚硝鎓或锑衍生物作为电子转移氧化剂来实现的，它们可以清洁地氧化底物供体，而不会在样品溶液中产生任何副产物。这种可靠的 ECD 光谱使我们能够全面检查有机自由基阳离子的手性，并将它们与相应的中性化合物进行比较。通过密度泛函理论 (DFT) 计算很好地模拟了观察到的手性氢醌醚的中性和自由基阳离子物质的 VCD 光谱，从中评估了溶液中每个自由基阳离子构象异构体的相对贡献。因此，综合合成、光谱和...
• 一种含双环化侧基结构的二胺单体及其制备方法与应用
  申请人：中国科学院宁波材料技术与工程研究所

  公开号：CN116023277A

  公开（公告）日：2023-04-28

  本发明公开了一种含双环化侧基结构的二胺单体及其制备方法与应用。所述含双环化侧基结构的二胺单体具有如下式中任一者所示的结构： 本发明中由含双环化侧基结构的二胺单体制备一系列聚酰亚胺薄膜，由于大体积双环取代基与中心苯环结合，显著提高了二胺单体的刚性和位阻，使得所制备的聚酰亚胺薄膜具有高比表面积和气体渗透系数，其气体分离性能优于商品化气体分离膜以及相对应的六氟二酐气体分离膜，在工业氢气纯化和回收应用方面有较好的应用前景。
• Diels; Alder, Chemische Berichte, 1929, vol. 62, p. 2357
  作者：Diels、Alder

  DOI：——

  日期：——
• Novel Catalysis of Hydroquinone Autoxidation with Nitrogen Oxides
  作者：E. Bosch、R. Rathore、J. K. Kochi

  DOI：10.1021/jo00088a039

  日期：1994.5

  An efficient catalytic method is described for the preparative conversion of hydroquinones to quinones with dioxygen under mild conditions. The use of the gaseous nitrogen oxide (NOx) catalyst allows a simple workup procedure for the isolation of quinones in essentially quantitative yields by merely removing the low-boiling solvent dichloromethane in vacuo. The mechanism of the catalytic autoxidation of hydroquinones is ascribed to the critical role of nitrosonium (NO+) in the one-electron oxidation of hydroquinone, followed by the reoxidation of the reduced nitric oxide (NO) with dioxygen. An extensive series of complex interchanges among various NOx species in nitrogen-(V), -(IV), -(III), and -(II) oxidation states, coupled with stepwise oxidation of hydroquinone via a successive series of one-electron/proton transfers, form the critical components of the catalytic cycle.
• Rathore Rajendra, Bosch Eric, Kochi Jay K., J. Chem. Soc. Perkin Trans. 2, (1994) N 6, S 1157- 1166
  作者：Rathore Rajendra, Bosch Eric, Kochi Jay K.

  DOI：——

  日期：——