5,7-dichloro-3,4-dihydro-2-<<(1,1-diethylethyl)dimethylsilyl>oxy>naphthalene | 99667-35-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 5,7-dichloro-3,4-dihydro-2-<<(1,1-diethylethyl)dimethylsilyl>oxy>naphthalene
• 英文别名: Tert-butyl-[(5,7-dichloro-3,4-dihydronaphthalen-2-yl)oxy]-dimethylsilane
• CAS: 99667-35-3
• 化学式: C₁₆H₂₂Cl₂OSi
• 分子量: 329.342
• InChiKey: ZPEVTICWDBKQLM-UHFFFAOYSA-N

物化性质

• 沸点：
  357.9±42.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,7-dichloro-3,4-dihydro-2-<<(1,1-diethylethyl)dimethylsilyl>oxy>naphthalene 在 sodium tetrahydroborate 、 氯化亚砜 、 碳酸氢钠 、 臭氧 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 methyl 3-<2,4-dichloro-6-(chloromethyl)phenyl>propanoate
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 2. Structural modification of 7-(substituted aryl)-3,5-dihydroxy-6-heptenoic acids and their lactone derivatives

  摘要：

  A series of 7-(substituted aryl)-3,5-dihydroxy-6-heptenoic (heptanoic) acids and their lactone derivatives have been prepared and tested for inhibition of 3-hydroxy-3-methylglutaryl-coenzyme A reductase in vitro. A systematic exploration of the structure-activity relationships in this series led to the synthesis of (+)-trans-(E)-6-[2-[2,4-dichloro-6-[(4-fluorophenyl) methoxyl]phenyl]ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (66(+)), which has one-half of the inhibitory activity of compactin.

  DOI：

  10.1021/jm00152a001
• 作为产物：
  描述：

  5,7-二氯-3,4-二氢-1H-2-萘酮 、 叔丁基二甲基氯硅烷 在 lithium diisopropyl amide 作用下， 生成 5,7-dichloro-3,4-dihydro-2-<<(1,1-diethylethyl)dimethylsilyl>oxy>naphthalene
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 2. Structural modification of 7-(substituted aryl)-3,5-dihydroxy-6-heptenoic acids and their lactone derivatives

  摘要：

  A series of 7-(substituted aryl)-3,5-dihydroxy-6-heptenoic (heptanoic) acids and their lactone derivatives have been prepared and tested for inhibition of 3-hydroxy-3-methylglutaryl-coenzyme A reductase in vitro. A systematic exploration of the structure-activity relationships in this series led to the synthesis of (+)-trans-(E)-6-[2-[2,4-dichloro-6-[(4-fluorophenyl) methoxyl]phenyl]ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (66(+)), which has one-half of the inhibitory activity of compactin.

  DOI：

  10.1021/jm00152a001

文献信息

• 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
  作者：G. E. Stokker、A. W. Alberts、P. S. Anderson、E. J. Cragoe、A. A. Deana、J. L. Gilfillan、J. Hirshfield、W. J. Holtz、W. F. Hoffman

  DOI：10.1021/jm00152a002

  日期：1986.2

  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.
• HOFFMAN, W. F.;ALBERTS, A. W.;CRAGOE, E. J. ,, JR.;DEANA, A. A.;EVANS, B.+, J. MED. CHEM., 1986, 29, N 2, 159-169
  作者：HOFFMAN, W. F.、ALBERTS, A. W.、CRAGOE, E. J. ,, JR.、DEANA, A. A.、EVANS, B.+

  DOI：——

  日期：——
• STOKKER, G. E.;ALBERTS, A. W.;ANDERSON, P. S.;CRAGOE, E. J. ,, JR.;DEANA,+, J. MED. CHEM., 1986, 29, N 2, 170-181
  作者：STOKKER, G. E.、ALBERTS, A. W.、ANDERSON, P. S.、CRAGOE, E. J. ,, JR.、DEANA,+

  DOI：——

  日期：——