9,10-Dimethoxy-1,4-ethano-5,8-methano-1,2,3,4,5,6,7,8-octahydroanthracene | 157870-34-3

• 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-Dimethoxy-1,4-ethano-5,8-methano-1,2,3,4,5,6,7,8-octahydroanthracene
• 英文别名: 3,10-Dimethoxypentacyclo[10.2.2.15,8.02,11.04,9]heptadeca-2(11),3,9-triene
• CAS: 157870-34-3
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: KKGHOJZCZLVERP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  9,10-Dimethoxy-1,4-ethano-5,8-methano-1,2,3,4,5,6,7,8-octahydroanthracene 生成 亚硝酸甲酯
  参考文献：
  名称：

  Rathore Rajendra, Bosch Eric, Kochi Jay K., J. Chem. Soc. Perkin Trans. 2, (1994) N 6, S 1157- 1166

  摘要：

  DOI：
• 作为产物：
  描述：

  3,10-dimethoxypentacyclo[10.2.2.15,8.02,11.04,9]heptadeca-2,4(9),10,13-tetraene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、551.58 kPa 条件下， 反应 3.0h， 以100%的产率得到9,10-Dimethoxy-1,4-ethano-5,8-methano-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

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

  DOI：——

  日期：——
• DURABLE ELECTROOPTIC DEVICES COMPRISING IONIC LIQUIDS
  申请人：Burrell Anthony K.

  公开号：US20080266642A1

  公开（公告）日：2008-10-30

  Electrolyte solutions for electrochromic devices such as rear view mirrors and displays with low leakage currents are prepared using inexpensive, low conductivity conductors. Preferred electrolytes include bifunctional redox dyes and molten salt solvents with enhanced stability toward ultraviolet radiation. The solvents include lithium or quaternary ammonium cations, and perfluorinated sulfonylimide anions selected from trifluoromethylsulfonate (CF 3 SO 3 − ), bis(trifluoromethylsulfonyl)imide ((CF 3 SO 2 ) 2 N − ), bis(perfluoroethylsulfonyl)imide ((CF 3 CF 2 SO 2 ) 2 N − ) and tris(trifluoromethylsulfonyl)methide ((CF 3 SO 2 ) 3 C − ). Electroluminescent, electrochromic and photoelectrochromic devices with nanostructured electrodes include ionic liquids with bifunctional redox dyes. Some of the electrolyte solutions color to red when devices employing the solutions are powered, leading to red or neutral electrooptic devices.
• Durable electrooptic devices comprising ionic liquids
  申请人：Burrell Anthony K.

  公开号：US20090103162A1

  公开（公告）日：2009-04-23

  Electrolyte solutions for electrochromic devices such as rear view mirrors and displays with low leakage currents are prepared using inexpensive, low conductivity conductors. Preferred electrolytes include bifunctional redox dyes and molten salt solvents with enhanced stability toward ultraviolet radiation. The solvents include lithium or quaternary ammonium cations, and perfluorinated sulfonylimide anions selected from trifluoromethylsulfonate (CF 3 SO 3 − ), bis(trifluoromethylsulfonyl)imide ((CF 3 SO 2 ) 2 N − ), bis(perfluoroethylsulfonyl)imide ((CF 3 CF 2 SO 2 ) 2 N − ) and tris(trifluoromethylsulfonyl)methide ((CF 3 SO 2 ) 3 C − ). Electroluminescent, electrochromic and photoelectrochromic devices with nanostructured electrodes include ionic liquids with bifunctional redox dyes. Some of the electrolyte solutions color to red when devices employing the solutions are powered, leading to red or neutral electrooptic devices.
• US7450292B1
  申请人：——

  公开号：US7450292B1

  公开（公告）日：2008-11-11
• US7633669B2
  申请人：——

  公开号：US7633669B2

  公开（公告）日：2009-12-15