Bis(9-anthryloxy)methane | 145428-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Bis(9-anthryloxy)methane
• 英文别名: 9-(Anthracen-9-yloxymethoxy)anthracene
• CAS: 145428-34-8
• 化学式: C₂₉H₂₀O₂
• 分子量: 400.477
• InChiKey: BXONVPPPHPFPSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 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：

  Bis(9-anthryloxy)methane 以 甲基环己烷 为溶剂， 反应 2.0h， 以75%的产率得到2,4-Dioxaoctacyclo[11.6.6.65,12.01,5.06,11.014,19.020,25.026,31]hentriaconta-6,8,10,14,16,18,20,22,24,26,28,30-dodecaene
  参考文献：
  名称：

  Synthesis, photoisomerization and molecular dynamics of bis(9-anthryloxy)methane: comparative study in solution and in the gas phase using the supersonic free jet technique

  摘要：

  The bichromophoric molecule, bis(9-anthryloxy)methane, in which two anthracene rings are connected by the highly flexible O-CH2-O link has been prepared and was shown to undergo very efficient photocyclomerization in the singlet state (PHI(R) = 0.36) compared to other bisanthracenes. The S0-S1 transition has been studied both in solution, using absorption and fluorescence spectroscopies, and in a supersonic free jet, using fluorescence excitation and dispersed emission spectroscopy. The kinetic data deduced from the temperature dependence of the fluorescence quantum yield in solution indicate a fast nonradiative process with an activation energy of 3.7 kcal/mol. The comparison of the fluorescence excitation with hole burning spectra obtained in a supersonic expansion shows that only one conformer is present in the jet and that the fast nonradiative process responsible for the quenching of fluorescence is taking place in the isolated gas-phase excited molecule with an energy threshold < 1 kcal/mol. This low barrier in the isolated molecule points to the role of the solvent which hinders the molecular motions necessary to reach the geometry leading to the photoproduct.

  DOI：

  10.1021/j100205a011
• 作为产物：
  描述：

  8,9-dihydro-3a,8[1',2']:9,13b[1:2']-dibenzenodibenzo[3,4:7:8]cycloocta[1,2-d]-1,3-dioxole 以 甲基环己烷 为溶剂， 生成 Bis(9-anthryloxy)methane
  参考文献：
  名称：

  Synthesis, photoreactivity and fluorescence properties of new bis -9-anthryloxymethanes

  摘要：

  The synthesis of new coloured anthryloxymethanes is described; they are reversibly transformed upon ir adiation into their colourless photocyclomers. Their high photoreactivity. accompanied by a weak fluorescence and short singlet excited lifetimes, originates in the great flexibility of the OCH2O spacer.

  DOI：

  10.1016/0040-4039(94)02482-q

文献信息

• Polar-Solvent Effect on the Photocycloisomerization of Symmetrical Bis[anthracenes]: A Transient Ultrafast Kinetic Study
  作者：Alexander S. Dvornikov、Jean-Pierre Desvergne、Dmitri A. Oulianov、Henri Bouas-Laurent、Peter M. Rentzepis

  DOI：10.1002/1522-2675(20010919)84:9<2520::aid-hlca2520>3.0.co;2-4

  日期：2001.9.19

  photoreactive properties. The 9,9′-[methylenebis(oxy)]bis[anthracenes] 1 (AOCH2OA) exhibit the highest known intramolecular photocycloaddition quantum yield from the S1 state and, moreover, display a higher yield in polar solvents, an unexpected result for symmetrical systems. No excimer fluorescence was detected in solution at room temperature. The 10,10′-dimethoxy derivative 1b was studied by picosecond

  双[蒽]是少数具有光反应性质的荧光非共轭双生色团。9,9'-[亚甲基双(氧基)]双[蒽] 1 (AOCH2OA) 从 S1 态表现出已知最高的分子内光环加成量子产率，此外，在极性溶剂中表现出更高的产率，这是对称系统的意外结果. 在室温下在溶液中未检测到准分子荧光。通过皮秒 (ps) 激光光谱研究了 10,10'-二甲氧基衍生物 1b。在非极性溶剂（甲基环己烷）中，SnS1 是唯一检测到的瞬态吸收，而在极性溶剂（MeCN）中，记录了第二个瞬态的增长和衰减，第二个瞬态归因于两性离子 A+。-A- .. 推导出动力学数据，
• Substituted bis-acridines and related compounds as CCR5 receptor ligands, anti-inflammatory agents and anti-viral agents
  申请人：SmithKline Beecham Corporation

  公开号：US20010031763A1

  公开（公告）日：2001-10-18

  This invention relates to substituted bis-acridines and related compounds which are ligands, in particular, antagonists of the CCR5 receptor. In addition, this invention relates to the treatment and prevention of disease states mediated by CCR5, including, but not limited to, asthma and atopic disorders (for example, atopic dermatitis and allergies), rheumatoid arthritis, atherosclerosis, psoriasis, autoimmune disease such as multiple sclerosis, and inflammatory bowel disease, all in mammals, by the use of substituted bis-acridines and related compounds which are CCR5 receptor antagonists. Also, since CCR5 is a co-receptor for the entry of HIV into cells, selective receptor ligands may be useful in the treatment of HIV infection.

  本发明涉及取代的双咯吩和相关化合物，它们是配体，特别是CCR5受体的拮抗剂。此外，本发明涉及通过使用取代的双咯吩和相关化合物作为CCR5受体拮抗剂来治疗和预防由CCR5介导的疾病状态，包括但不限于哮喘和过敏性疾病（例如过敏性皮炎和过敏症），类风湿性关节炎，动脉粥样硬化，牛皮癣，自身免疫疾病如多发性硬化症和炎症性肠病等哺乳动物疾病。此外，由于CCR5是HIV进入细胞的共受体，选择性受体配体可以用于治疗HIV感染。
• SUBSTITUTED BIS-ACRIDINES AND RELATED COMPOUNDS AS CCR5 RECEPTOR LIGANDS, ANTI-INFLAMMATORY AGENTS AND ANTI-VIRAL AGENTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0979078A1

  公开（公告）日：2000-02-16
• EP0979078A4
  申请人：——

  公开号：EP0979078A4

  公开（公告）日：2000-06-21
• US6242459B1
  申请人：——

  公开号：US6242459B1

  公开（公告）日：2001-06-05