methyl-8-trifluoromethyl-dibenzotricyclo<3.3.0.0^2,8>octa-3,6-dien-1-carboxylate | 147217-98-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: methyl-8-trifluoromethyl-dibenzotricyclo<3.3.0.0^2,8>octa-3,6-dien-1-carboxylate
• 英文别名: methyl 2-(trifluoromethyl)pentacyclo[7.7.0.02,16.03,8.010,15]hexadeca-3,5,7,10,12,14-hexaene-1-carboxylate
• CAS: 147217-98-9
• 化学式: C₁₉H₁₃F₃O₂
• 分子量: 330.306
• InChiKey: UXGKXDSYIJIWCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl-1-trifluoromethyl-dibenzobicyclo<2.2.2>octa-2,5,7-triene-8-carboxylate 以 丙酮 为溶剂， 反应 40.0h， 以51%的产率得到methyl-8-trifluoromethyl-dibenzotricyclo<3.3.0.0^2,8>octa-3,6-dien-1-carboxylate
  参考文献：
  名称：

  Regiospecific synthesis and structural study of some trifluoromethyl substituted dibenzosemibullvalenes

  摘要：

  Preparation of the regiospecifically trifluoromethyl substituted dibenzosemibullvalenes 3 and 5 is described. An unequivocal proof of chirality of 3 and 5 was obtained by enrichment of their enantiomers using liquid chromatography on triacetyl- or tribenzoylcellulose. The stereostructure of compounds 3 to 5 was proved by their H-1-NMR spectra and confirmed by X-ray crystallographic analysis. The geometrical data from X-ray structural analyses showed that five-membered rings involved in the skeleton of 3 and 5 adopt flattened envelope conformations. These results indicate also a significant substituent-induced bond length asymmetry in the cyclopropane rings of 3 and 5.

  DOI：

  10.1007/bf00808282

文献信息

• Regiospecific synthesis and structural study of some trifluoromethyl substituted dibenzosemibullvalenes
  作者：Klaudio Otočan、Mladen Mintas、Fritz Kastner、Albrecht Mannschreck、James A. Golen、Paul G. Williard

  DOI：10.1007/bf00808282

  日期：1992.12

  Preparation of the regiospecifically trifluoromethyl substituted dibenzosemibullvalenes 3 and 5 is described. An unequivocal proof of chirality of 3 and 5 was obtained by enrichment of their enantiomers using liquid chromatography on triacetyl- or tribenzoylcellulose. The stereostructure of compounds 3 to 5 was proved by their H-1-NMR spectra and confirmed by X-ray crystallographic analysis. The geometrical data from X-ray structural analyses showed that five-membered rings involved in the skeleton of 3 and 5 adopt flattened envelope conformations. These results indicate also a significant substituent-induced bond length asymmetry in the cyclopropane rings of 3 and 5.