13-methyl-8,10,12-trioxapentacyclo[5.5.2.0^2,6.O^3,11.0^5,9]-13-tetradecene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: 13-methyl-8,10,12-trioxapentacyclo[5.5.2.0^2,6.O^3,11.0^5,9]-13-tetradecene
• 英文别名: 6-methyl-2,4,14-trioxapentacyclo[6.5.1.03,11.05,10.09,13]tetradec-6-ene
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: YUDBAPNEZDQABR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (+/-)-6-methyl-(4arH.8acH)-1.4.4a.8a-tetrahydro-1c.4c-methano-naphthalene-quinone-(5.8) 在 sodium tetrahydroborate 、 cerium(III) chloride 、 二甲基硫 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 13-methyl-8,10,12-trioxapentacyclo[5.5.2.0^2,6.O^3,11.0^5,9]-13-tetradecene
  参考文献：
  名称：

  Synthesis of New Type Diacetal Trioxa-Cage Compounds via an Intramolecular Nucleophilic Addition of the Hydroxy Group to the Carbonyl Oxide Group

  摘要：

  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.

  DOI：

  10.1021/jo980632s