4'-(tert-butyldimethylsilyloxy)-3-chlorobiphenyl-4-carbaldehyde | 716344-14-8

• 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: 4'-(tert-butyldimethylsilyloxy)-3-chlorobiphenyl-4-carbaldehyde
• 英文别名: 4'-{[tert-butyl(dimethyl)silyl]oxy}-3-chloro-1,1'-biphenyl-4-carbaldehyde；4'-{[Tert-butyl(dimethyl)silyl]oxy}-3-chloro-1,1'-biphenyl-4-carbaldehyde；4-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-chlorobenzaldehyde
• CAS: 716344-14-8
• 化学式: C₁₉H₂₃ClO₂Si
• 分子量: 346.929
• InChiKey: JCYGEIPIZAQNQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-(tert-butyldimethylsilyloxy)-3-chlorobiphenyl-4-carbaldehyde 在 吡啶 、 盐酸羟胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.67h， 生成 (E)-3-chloro-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：

  2-氯-4-羟基苯甲醛 在 四(三苯基膦)钯 吡啶 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 4'-(tert-butyldimethylsilyloxy)-3-chlorobiphenyl-4-carbaldehyde
  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

• Hydroxy-biphenyl-carbaldehyde oxime derivatives and their use as estrogenic agents
  申请人：Mewshaw Eric Richard

  公开号：US20050020676A1

  公开（公告）日：2005-01-27

  This invention provides estrogen receptor modulators having the structure: wherein R 1 to R 6 and R 8 are as defined in the specification; or a pharmaceutically acceptable salt thereof.

  本发明提供了具有以下结构的雌激素受体调节剂：其中R1至R6和R8的定义如规范中所述；或其药学上可接受的盐。
• Hydroxy-Biphenyl-Carbaldehyde Oxime Derivatives and Their Use As Estrogenic Agents
  申请人：Mewshaw Eric Richard

  公开号：US20080033049A1

  公开（公告）日：2008-02-07

  This invention provides estrogen receptor modulators having the structure: wherein R 1 to R 6 and R 8 are as defined in the specification; or a pharmaceutically acceptable salt thereof.

  该发明提供了具有以下结构的雌激素受体调节剂：其中R1至R6和R8如规范中定义；或其药用盐。
• Synthesis and Structure Confirmation of Selagibenzophenone C
  作者：Dominik Kunák、Miguel Mateus、Lukas Rycek

  DOI：10.1002/ejoc.202200014

  日期：2022.3.22

  Plants from the genus Selaginella are a source of natural products with diverse structural motifs. In this wok, the first synthesis of diarylbenzophenone selagibenzophenone C, recently isolated from Selaginella tamariscina, is reported.

  卷柏属植物是具有多种结构图案的天然产物的来源。在此锅中，报道了最近从柽柳卷柏中分离得到的二芳基二苯甲酮卷柏二苯甲酮 C 的首次合成。
• 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.