4'-(tert-butyldimethylsilyloxy)-2-fluorobiphenyl-4-carbaldehyde oxime

• 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: 4'-(tert-butyldimethylsilyloxy)-2-fluorobiphenyl-4-carbaldehyde oxime
• 英文别名: 4'-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoro-1,1'-biphenyl-4-carbaldehyde oxime；(NE)-N-[[4-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-fluorophenyl]methylidene]hydroxylamine
• 化学式: C₁₉H₂₄FNO₂Si
• 分子量: 345.489
• InChiKey: GNJXYEIYINWCNH-FYJGNVAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-(tert-butyldimethylsilyloxy)-2-fluorobiphenyl-4-carbaldehyde oxime 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以84%的产率得到(E)-2-fluoro-4'-hydroxybiphenyl-4-carbaldehyde oxime
  参考文献：
  名称：

  ERβ Ligands. Part 2: Synthesis and structure–activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives

  摘要：

  A series of biphenyl carbaldehyde oximes (6) was prepared and shown to have significant selectivity for the estrogen receptor-beta (ERbeta). The exploitation of the oxime moiety as a hydrogen bond donating group, which mimicked the C-ring of genistein makes these compounds unique. Molecular modeling studies showed the oxime moiety hydrogen bonding to the histidine residue, which was supported by the structure-activity relationships. The most potent compounds in this study had IC50 values in a radio-liaand binding assay of between 8-35 nM. Among the most selective compounds were 6i and 6s (49- and 31-fold ERbeta selective, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.028
• 作为产物：
  描述：

  4-(叔丁基二甲基硅氧基)苯基硼酸 在 四(三苯基膦)钯 吡啶 、 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 7.0h， 生成 4'-(tert-butyldimethylsilyloxy)-2-fluorobiphenyl-4-carbaldehyde oxime
  参考文献：
  名称：

  ERβ Ligands. Part 2: Synthesis and structure–activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives

  摘要：

  A series of biphenyl carbaldehyde oximes (6) was prepared and shown to have significant selectivity for the estrogen receptor-beta (ERbeta). The exploitation of the oxime moiety as a hydrogen bond donating group, which mimicked the C-ring of genistein makes these compounds unique. Molecular modeling studies showed the oxime moiety hydrogen bonding to the histidine residue, which was supported by the structure-activity relationships. The most potent compounds in this study had IC50 values in a radio-liaand binding assay of between 8-35 nM. Among the most selective compounds were 6i and 6s (49- and 31-fold ERbeta selective, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.028

文献信息

• ERβ Ligands. Part 2: Synthesis and structure–activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives
  作者：Cuijian Yang、Richard Edsall、Heather A Harris、Xiaochun Zhang、Eric S Manas、Richard E Mewshaw

  DOI：10.1016/j.bmc.2004.03.028

  日期：2004.5

  A series of biphenyl carbaldehyde oximes (6) was prepared and shown to have significant selectivity for the estrogen receptor-beta (ERbeta). The exploitation of the oxime moiety as a hydrogen bond donating group, which mimicked the C-ring of genistein makes these compounds unique. Molecular modeling studies showed the oxime moiety hydrogen bonding to the histidine residue, which was supported by the structure-activity relationships. The most potent compounds in this study had IC50 values in a radio-liaand binding assay of between 8-35 nM. Among the most selective compounds were 6i and 6s (49- and 31-fold ERbeta selective, respectively). (C) 2004 Elsevier Ltd. All rights reserved.