2-{2-[3-Methoxy-bicyclo[4.2.0]octa-1,3,5-trien-(7E)-ylidene]-ethyl}-2-trifluoromethyl-cyclopentane-1,3-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-{2-[3-Methoxy-bicyclo[4.2.0]octa-1,3,5-trien-(7E)-ylidene]-ethyl}-2-trifluoromethyl-cyclopentane-1,3-dione
• 英文别名: 2-[(2E)-2-(3-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienylidene)ethyl]-2-(trifluoromethyl)cyclopentane-1,3-dione
• 化学式: C₁₇H₁₅F₃O₃
• 分子量: 324.3
• InChiKey: VFNKEBJDVCGBIN-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-{2-[3-Methoxy-bicyclo[4.2.0]octa-1,3,5-trien-(7E)-ylidene]-ethyl}-2-trifluoromethyl-cyclopentane-1,3-dione 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以80%的产率得到2-<2-(4-methoxybenzocyclobuten-1-yl)ethyl>-2-trifluoromethylcyclopentane-1,3-dione
  参考文献：
  名称：

  The angular trifluoromethyl group. V. Total synthesis and biological properties of 14-dehydro-18,18,18-trifluoro-19-nortestosterone

  摘要：

  The total synthesis of the 18,18,18-trifluoro analogue (FDNT) of 14-dehydro-19-nortestosterone (DNT) was performed using the intramolecular Diels-Alder reaction of an ortho-quinodimethane. Unlike 18,18,18-trifluoro-19-nortestosterone (FNT), FDNT showed in vitro and in vivo biological properties (binding affinity for the androgen receptor and growth stimulation of ventral prostate and seminal vesicles) comparable with its unfluorinated counterpart (DNT). The diverging behaviour of FNT and FDNT is tentatively ascribed to a difference in ring-D geometry.

  DOI：

  10.1016/0223-5234(94)90154-6
• 作为产物：
  描述：

  2-(三氟甲基)环戊烷-1,3-二酮 、 2-<2-(4-methoxybenzocyclobuten-1-yl)ethyl>-2-trifluoromethylcyclopentane-1,3-dione 在 三乙胺 作用下， 以 苯 为溶剂， 反应 72.0h， 以16%的产率得到2-{2-[3-Methoxy-bicyclo[4.2.0]octa-1,3,5-trien-(7E)-ylidene]-ethyl}-2-trifluoromethyl-cyclopentane-1,3-dione
  参考文献：
  名称：

  The angular trifluoromethyl group. V. Total synthesis and biological properties of 14-dehydro-18,18,18-trifluoro-19-nortestosterone

  摘要：

  The total synthesis of the 18,18,18-trifluoro analogue (FDNT) of 14-dehydro-19-nortestosterone (DNT) was performed using the intramolecular Diels-Alder reaction of an ortho-quinodimethane. Unlike 18,18,18-trifluoro-19-nortestosterone (FNT), FDNT showed in vitro and in vivo biological properties (binding affinity for the androgen receptor and growth stimulation of ventral prostate and seminal vesicles) comparable with its unfluorinated counterpart (DNT). The diverging behaviour of FNT and FDNT is tentatively ascribed to a difference in ring-D geometry.

  DOI：

  10.1016/0223-5234(94)90154-6