6-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-oxo-5-hexen-4-yl 2-bromoacetate | 99725-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-oxo-5-hexen-4-yl 2-bromoacetate
• CAS: 99725-11-8
• 化学式: C₂₃H₂₄BrFO₃
• 分子量: 447.344
• InChiKey: RFZGJYMJUGYMRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-oxo-5-hexen-4-yl 2-bromoacetate 在 氯化二乙基铝 、 copper(I) bromide 、 锌 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以34%的产率得到(E)-6-<2-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethynyl>-3,4,5,6-tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-one
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 3. 7-(3,5-Disubstituted-[1,1'-biphenyl]-2-yl)-3,5-dihydroxy-6-heptenoic acids and their lactone derivatives

  摘要：

  The syntheses of a series of 7-(3,5-disubstituted [1,1'-bephenyl]-2-yl)-3,5-dihydroxy-6-heptenoic acids and their lactones are reported. Intrinsic 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitory activity is enhanced markedly when the biphenyl moiety is substituted by chloro or methyl groups at positions 3 and 5 and a fluoro group at position 4'. These substitutions, followed by resolution, provided compounds 100(+) and 110(+) with 2.8 times the intrinsic inhibitory activity of compactin. Compound 100(+) was shown to possess the same chirality in the lactone ring as compactin by single-crystal X-ray crystallography.

  DOI：

  10.1021/jm00152a002
• 作为产物：
  描述：

  E-3-(4'-fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl)-2-propenal 在 吡啶 、 丙二酸 、 三正丁基甲氧基锡 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 6-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-oxo-5-hexen-4-yl 2-bromoacetate
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 3. 7-(3,5-Disubstituted-[1,1'-biphenyl]-2-yl)-3,5-dihydroxy-6-heptenoic acids and their lactone derivatives

  摘要：

  The syntheses of a series of 7-(3,5-disubstituted [1,1'-bephenyl]-2-yl)-3,5-dihydroxy-6-heptenoic acids and their lactones are reported. Intrinsic 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitory activity is enhanced markedly when the biphenyl moiety is substituted by chloro or methyl groups at positions 3 and 5 and a fluoro group at position 4'. These substitutions, followed by resolution, provided compounds 100(+) and 110(+) with 2.8 times the intrinsic inhibitory activity of compactin. Compound 100(+) was shown to possess the same chirality in the lactone ring as compactin by single-crystal X-ray crystallography.

  DOI：

  10.1021/jm00152a002