(+/-)-5.8-dioxo-6-phenyl-(4arH.8acH)-1.4.4a.5.8.8a-hexahydro-1c.4c-methano-naphthalene | 65254-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-5.8-dioxo-6-phenyl-(4arH.8acH)-1.4.4a.5.8.8a-hexahydro-1c.4c-methano-naphthalene
• 英文别名: (+/-)-5.8-Dioxo-6-phenyl-(4arH.8acH)-1.4.4a.5.8.8a-hexahydro-1c.4c-methano-naphthalin；(1R,2S,7R,8S)-4-phenyltricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione
• CAS: 65254-20-8；93382-02-6
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: FBCSKRIOXNULOU-KNPMLCFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-5.8-dioxo-6-phenyl-(4arH.8acH)-1.4.4a.5.8.8a-hexahydro-1c.4c-methano-naphthalene 在 铂 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 endo-cis-2-Phenyl-5,8-methano-4a,5,6,7,8,8a-hexahydro-1,4-naphthochinon
  参考文献：
  名称：

  有机光化学研究。第十部分。环己烯-1,4-二酮向烯烃和乙炔的光化学加成

  摘要：

  照明烯-1,4-二酮（Ia）的（λ> 325毫微米） -烯烃和炔烃的存在（IE）给出的四环衍生物〔8,2,1,0 2,9，0 4,7 ]十三烷[例如，（II）]。该反应似乎涉及烯二酮的亲电子3（ππ *）状态，该状态通过类似于最稳定的双自由基中间体的过渡态加到烯烃中。

  DOI：

  10.1039/j39690000105
• 作为产物：
  描述：

  环戊二烯 、 苯基-P-苯醌 在 甲醇 作用下， 生成 (+/-)-5.8-dioxo-6-phenyl-(4arH.8acH)-1.4.4a.5.8.8a-hexahydro-1c.4c-methano-naphthalene
  参考文献：
  名称：

  Model Experiments on the Use of Cyclopentadiene in the Synthesis of Sterol-like Compounds¹

  摘要：

  DOI：

  10.1021/ja01246a506

文献信息

• SYNTHESES AND REACTIONS OF SUBSTITUTED α-NAPHTHOQUINONES
  作者：ERNST BERGMANN、FELIX BERGMANN

  DOI：10.1021/jo01219a005

  日期：1938.5
• Synthesis of New Type Diacetal Trioxa-Cage Compounds via an Intramolecular Nucleophilic Addition of the Hydroxy Group to the Carbonyl Oxide Group
  作者：Hsien-Jen Wu、Ching-Shiun Chao、Chu-Chung Lin

  DOI：10.1021/jo980632s

  日期：1998.10.1

  The synthesis of diacetal trioxa-cage compounds with a new type of skeleton is reported. Ozonolysis of the diols 2a-f, 21, 24, and 33 in CH2Cl2 at -78 degrees C followed by reduction with Me2S gave the diacetal trioxa-cages 3a-f, 22, 25, and 34 in 70-80% yields, respectively. A mechanism via an intramolecular nucleophilic addition of the hydroxy group of the diols to the carbonyl oxide group is proposed for the formation of the diacetal trioxa-cages. The effect of the number of carbon atoms at the bridge of the diols on the formation of the diacetal trioxa-cage skeleton was examined. Ozonolysis of the diols 13 and 15 under the same reaction conditions gave compounds 16 and 18, respectively. No detectable amount of the trioxa-cages 17 and 19 was obtained. For the synthesis of the diacetal trioxa-cages 28a-c and 31, which possess an alkene bond intact, ozonolysis of the diols 27a-c and 30 was performed by controlling the amount of ozone.