2,7-dimethoxynaphtho[1,8-c,d][1,2]diselenole | 1314930-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,7-dimethoxynaphtho[1,8-c,d][1,2]diselenole
• 英文别名: 3,8-dimethoxynaphtho[1,8-cd]-1,2-diselenole；5,11-Dimethoxy-2,3-diselenatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene；5,11-dimethoxy-2,3-diselenatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene
• CAS: 1314930-32-9
• 化学式: C₁₂H₁₀O₂Se₂
• 分子量: 344.13
• InChiKey: OLUABFIXXFWHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2,7-dimethoxynaphtho[1,8-c,d][1,2]diselenole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以73%的产率得到3,8-dimethoxynaphtho[1,8-cd]-1,2-diselenole Se-oxide
  参考文献：
  名称：

  Enhanced Glutathione Peroxidase Activity of Conformationally Restricted Naphthaleneperi-Dichalcogenides

  摘要：

  Conformationally restricted naphthalene peri-diselenides function as glutathione peroxidase mimetics with superior catalytic activity to that displayed by typical acyclic diaryl diselenides. Their activity was increased by electron-donating methoxy substituents, while a further 100-fold increase was observed with the corresponding ditelluride.

  DOI：

  10.1021/ol201617t
• 作为产物：
  描述：

  2,7-二甲氧基萘 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 10.5h， 生成 2,7-dimethoxynaphtho[1,8-c,d][1,2]diselenole
  参考文献：
  名称：

  Enhanced Glutathione Peroxidase Activity of Conformationally Restricted Naphthaleneperi-Dichalcogenides

  摘要：

  Conformationally restricted naphthalene peri-diselenides function as glutathione peroxidase mimetics with superior catalytic activity to that displayed by typical acyclic diaryl diselenides. Their activity was increased by electron-donating methoxy substituents, while a further 100-fold increase was observed with the corresponding ditelluride.

  DOI：

  10.1021/ol201617t

文献信息

• [FeFe]-Hydrogenase Synthetic Mimics Based on <i>Peri</i>-Substituted Dichalcogenides
  作者：Carlotta Figliola、Louise Male、Peter N. Horton、Mateusz B. Pitak、Simon J. Coles、Sarah L. Horswell、Richard S. Grainger

  DOI：10.1021/om500683p

  日期：2014.9.8

  Eight dithiolato-, diselenolato-, and mixed S,Se-Fe-2(CO)(6) complexes based on pen-substituted naphthalene and phenanthrene dichalcogenides are prepared by oxidative insertion of Fe-3(CO)(12) into the dichalcogen bonds of 2,7-dimethoxynaphtho[1,8cd][1,2]dithiole, three naphtho[1,8-cd][1,2]diselenoles, two naphtho[1,8-cd][1,2]thiaselenoles, phenanthro[1,10-cd][1,2]dithiole, and phenanthro[1,10-cd] [1,2]diselenole. Complexes are characterized by H-1, C-13 NMR, UV/vis, and IR spectroscopy and by X-ray analysis. The effect of replacing sulfur with selenium, incorporating electron-donating groups (2,7-di-ten-butyl, 2,7-climethoxy) on the naphthalene ring system, and changing the degree of conjugation in the aromatic backbone (naphthalene vs phenanthrene) on the reduction potential is evaluated by cyclic voltammetry. The electrocatalytic activity of these [FeFe]-hydrogenase synthetic mimics for proton reduction in the presence of increasing concentrations of p-TsOH is investigated. Diselenolate-based [FeFe]-complexes show enhanced catalytic activity for proton reduction compared with their sulfur congeners.
• Charge transfer complexes of electron-rich naphthalene peri-dichalcogenides with TCNQ
  作者：David J. Press、Thomas G. Back、Todd C. Sutherland

  DOI：10.1016/j.tetlet.2012.01.068

  日期：2012.3

  The electronic structures of several highly electron-rich 2,7-dimethoxynaphthalene peri-dichalcogenides were evaluated using optical and electrochemical methods, as well as by DFT calculations. Charge transfer complexes were formed with tetracyanoquinodimethane and resulted in absorption features that span from 300 nm to 1600 nm and HOMO-LUMO energy gaps as low as 0.8 eV. (C) 2012 Elsevier Ltd. All rights reserved.