1,5-Bis(4-methoxyphenyl)-6,7-dioxabicyclo<3.2.2>nonane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,5-Bis(4-methoxyphenyl)-6,7-dioxabicyclo<3.2.2>nonane
• 英文别名: (1R,5S)-1,5-bis(4-methoxyphenyl)-6,7-dioxabicyclo[3.2.2]nonane
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: FZFAHCBBNWRWFF-OYRHEFFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-Bis(4-methoxyphenyl)-6,7-dioxabicyclo<3.2.2>nonane 在 iron(II) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以78%的产率得到4-甲氧基苯酚
  参考文献：
  名称：

  Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: direct evidence for nucleophilic O-1,2-aryl shifts

  摘要：

  1,5-Diaryt-6.7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph. 1e: Ar=p-MeC6H4. 1d: Ar=pMeOC(6)H(4)) were prepared by a modified method of photo-electron transfer oxygenation. and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(Il)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products. 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00166-1
• 作为产物：
  描述：

  2,6-Bis(4-methoxyphenyl)-1,6-heptadiene 在 氧气 作用下， 生成 1,5-Bis(4-methoxyphenyl)-6,7-dioxabicyclo<3.2.2>nonane
  参考文献：
  名称：

  基于机制的简单，对称，易于制备的有效抗疟原过氧化物的设计

  摘要：

  基于机理的设计，两步合成和体外抗疟测试表明，热稳定的结晶双环内过氧化物2a和2b是有效的抗疟药。其通过FeBr还原2个前进通过氧基团，然后碳自由基经历β-断裂以形成烯烃和高价FeO物种。

  DOI：

  10.1016/0040-4039(95)02329-1

文献信息

• Mechanism-based design of simple, symmetrical, easily prepared, potent antimalarial endoperoxides
  作者：Gary H. Posner、Dasong Wang、Lluïsa González、Xueliang Tao、Jared N. Cumming、Donna Klinedinst、Theresa A. Shapiro

  DOI：10.1016/0040-4039(95)02329-1

  日期：1996.2

  Mechanism-based design, two-step synthesis, and in vitro antimalarial testing showed thermally stable, crystalline, bicyclic endoperoxides 2a and 2b to be potent antimalarials. Their reduction by FeBr2 proceeds via oxy-radicals and then carbon radicals that undergo β-scission to form an alkene and a high-valent FeO species.

  基于机理的设计，两步合成和体外抗疟测试表明，热稳定的结晶双环内过氧化物2a和2b是有效的抗疟药。其通过FeBr还原2个前进通过氧基团，然后碳自由基经历β-断裂以形成烯烃和高价FeO物种。
• Griesbeck, Axel G.; Sadlek, Oliver; Polborn, Kurt, Liebigs Annalen, 1996, # 4, p. 545 - 549
  作者：Griesbeck, Axel G.、Sadlek, Oliver、Polborn, Kurt

  DOI：——

  日期：——
• Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: direct evidence for nucleophilic O-1,2-aryl shifts
  作者：Masaki Kamata、Motoko Ohta、Ken-ichi Komatsu、Hye-Sook Kim、Yusuke Wataya

  DOI：10.1016/s0040-4039(02)00166-1

  日期：2002.3

  1,5-Diaryt-6.7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph. 1e: Ar=p-MeC6H4. 1d: Ar=pMeOC(6)H(4)) were prepared by a modified method of photo-electron transfer oxygenation. and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(Il)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products. 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.