2-(4-fluoro-3-methylphenyl)-4-(t-butyldimethylsilyl)-oxy-6,6-dimethylcyclohex-1-enecarboxaldehyde | 131114-08-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 2-(4-fluoro-3-methylphenyl)-4-(t-butyldimethylsilyl)-oxy-6,6-dimethylcyclohex-1-enecarboxaldehyde
• 英文别名: 4-[Tert-butyl(dimethyl)silyl]oxy-2-(4-fluoro-3-methylphenyl)-6,6-dimethylcyclohexene-1-carbaldehyde
• CAS: 131114-08-4
• 化学式: C₂₂H₃₃FO₂Si
• 分子量: 376.587
• InChiKey: QLFFNMDDWLHHPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-fluoro-3-methylphenyl)-4-(t-butyldimethylsilyl)-oxy-6,6-dimethylcyclohex-1-enecarboxaldehyde 在 水 、 silica gel 、 lithium diisopropyl amide 作用下， 以 正己烷 、 乙酸乙酯 为溶剂， 反应 5.5h， 生成 methyl 7-<2-(4-fluoro-3-methylphenyl)-4-(R,S)-(t-butyldimethylsilyl)oxy-6,6-dimethylcyclohex-1-en-1-yl>-5-(R,S)-hydroxy-3-oxohept-6-en-oate
  参考文献：
  名称：

  Inhibitors of HMG-CoA reductase. Biological effects of A 6-[2-[2-(4-fluoro-3-methylphenyl)-4-substituted cyclohexe-1-en-1-yl]ethenyl]-4-hydroxy-3,4,5,6-tetrahydro-2h-pyran-2-one

  摘要：

  We report on a series of potent inhibitors of HMG-CoA reductase (HMGR) that were designed to examine the biological consequences that result from molecular changes in RG 12561. The introduction of functional groups on the cyclohexene nucleus of RG 12561 and the resulting inhibitor-enzyme interactions at remote binding sites of HMGR are discussed. Cellular membrane permeability may also contribute to potency. The HMGR inhibitory activity was measured utilizing solubilized enzyme. The compounds were evaluated as inhibitors of sterol biosynthesis in vitro using liver slices and in vivo after oral administration to the rat.

  DOI：

  10.1016/0223-5234(92)90095-i
• 作为产物：
  描述：

  4-氟-3-甲基苯乙酮 在 咪唑 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 potassium tert-butylate 、 三氧化硫吡啶 、 苄基三甲基氢氧化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 2-(4-fluoro-3-methylphenyl)-4-(t-butyldimethylsilyl)-oxy-6,6-dimethylcyclohex-1-enecarboxaldehyde
  参考文献：
  名称：

  Inhibitors of HMG-CoA reductase. Biological effects of A 6-[2-[2-(4-fluoro-3-methylphenyl)-4-substituted cyclohexe-1-en-1-yl]ethenyl]-4-hydroxy-3,4,5,6-tetrahydro-2h-pyran-2-one

  摘要：

  We report on a series of potent inhibitors of HMG-CoA reductase (HMGR) that were designed to examine the biological consequences that result from molecular changes in RG 12561. The introduction of functional groups on the cyclohexene nucleus of RG 12561 and the resulting inhibitor-enzyme interactions at remote binding sites of HMGR are discussed. Cellular membrane permeability may also contribute to potency. The HMGR inhibitory activity was measured utilizing solubilized enzyme. The compounds were evaluated as inhibitors of sterol biosynthesis in vitro using liver slices and in vivo after oral administration to the rat.

  DOI：

  10.1016/0223-5234(92)90095-i

文献信息

• Inhibitors of HMG-CoA reductase. Biological effects of A 6-[2-[2-(4-fluoro-3-methylphenyl)-4-substituted cyclohexe-1-en-1-yl]ethenyl]-4-hydroxy-3,4,5,6-tetrahydro-2h-pyran-2-one
  作者：JR Regan、JG Bruno、K Gustafson、D Amin、K Neuenschwander、M Perrone

  DOI：10.1016/0223-5234(92)90095-i

  日期：1992.10

  We report on a series of potent inhibitors of HMG-CoA reductase (HMGR) that were designed to examine the biological consequences that result from molecular changes in RG 12561. The introduction of functional groups on the cyclohexene nucleus of RG 12561 and the resulting inhibitor-enzyme interactions at remote binding sites of HMGR are discussed. Cellular membrane permeability may also contribute to potency. The HMGR inhibitory activity was measured utilizing solubilized enzyme. The compounds were evaluated as inhibitors of sterol biosynthesis in vitro using liver slices and in vivo after oral administration to the rat.