(1R,4S,4aS,8bR)-1,4,4a,8b-methanonaphthalene-5,8-dione | 30763-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4S,4aS,8bR)-1,4,4a,8b-methanonaphthalene-5,8-dione
• CAS: 30763-65-6
• 化学式: C₁₃H₁₀O₂
• 分子量: 198.221
• InChiKey: GVDSTEYEJOZLDH-FIPCFZRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,4S,4aS,8bR)-1,4,4a,8b-methanonaphthalene-5,8-dione 在 对苯二酚 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Kaupp,G.; Prinzbach,H., Chemische Berichte, 1971, vol. 104, p. 182 - 204

  摘要：

  DOI：
• 作为产物：
  描述：

  在 对苯醌 作用下， 以 乙腈 为溶剂， 生成 (1R,4S,4aS,8bR)-1,4,4a,8b-methanonaphthalene-5,8-dione
  参考文献：
  名称：

  Kaupp,G.; Prinzbach,H., Chemische Berichte, 1971, vol. 104, p. 182 - 204

  摘要：

  DOI：

文献信息

• On the tendency of 1,2,3,6-tetrahydrobenzocyclobutene-3,6-diones for undergoing site-selective Diels-Alder reactions at the internal double bond
  作者：Daniel F. Rothenfluh、Donald C. Craig、Michael N. Paddon-Row

  DOI：10.1016/0040-4039(94)02413-6

  日期：1995.2

  Diels-Alder reactions of cyclobutene-3,6-diones, 5 and 6 with dienes 7 – 10 gave predominantly adducts arising from attack of the diene at the internal double bond of the diones. Ab initio MO calculations suggest that the observed site selectivity of cyclobutene-3,6-diones is due to strain effects rather that to frontier orbital effects.

  环丁烯3,6-二酮5和6与二烯7-10的Diels-Alder反应主要产生由于二烯在二酮内部双键上的进攻而引起的加合物。从头算MO的计算表明，观察到的环丁烯3,6-二酮的位点选择性是由于应变效应而不是边界轨道效应引起的。
• Benzoquinone‐ and Naphthoquinone‐Bearing Polymers Synthesized by Ring‐Opening Metathesis Polymerization as Cathode Materials for Lithium‐Ion Batteries
  作者：Yeqing Shi、Pengfei Sun、Jixing Yang、Yunhua Xu

  DOI：10.1002/cssc.201902966

  日期：2020.1.19

  AbstractOrganic electrode materials have attracted great interest for next‐generation lithium‐ion batteries owing to their merits of low cost, resource sustainability, and environmental friendliness. Dissolution in organic electrolyte is one of critical factors that limit their development, and constructing corresponding polymers is an effective way to prevent it. Herein, the synthesis of benzoquinone‐ and naphthoquinone‐bearing polymers by ring‐opening metathesis polymerization of monomers with an exo‐type four‐membered ring between polymerizable norbornene and redox‐active quinone units is reported. They exhibit significantly reduced solubility and clearly enhanced electrochemical performance. In particular, a high capacity (189.7 mAh g−1 at 0.1 C, 1 C=216.1 mA g−1), stable cycling (75.6 % capacity retention after 500 cycles at 2 C), and good rate capability (retaining 80.4 % from 0.1 to 2 C) were obtained for the naphthoquinone‐bearing polymer, which stand out among naphthoquinone‐bearing polymer electrode materials. This work offers rational molecular design and a new polymerization strategy to construct high‐performance polymer electrode materials.