3,4-Diphenylsalicylaldehyde | 377741-27-0

• 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: 3,4-Diphenylsalicylaldehyde
• 英文别名: 2-Hydroxy-3,4-diphenylbenzaldehyde
• CAS: 377741-27-0
• 化学式: C₁₉H₁₄O₂
• 分子量: 274.319
• InChiKey: KOPNOIVAGMGWKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-Diphenylsalicylaldehyde 在 盐酸羟胺 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以79%的产率得到3,4-Diphenylsalicylaldoxime
  参考文献：
  名称：

  Salicylaldoxime Moiety as a Phenolic “A-Ring” Substitute in Estrogen Receptor Ligands

  摘要：

  The phenolic "A-ring" of natural and synthetic estrogen receptor (ER) ligands was effectively replaced by a planar six-member ring formed through an intramolecular hydrogen bond within a salicylaldoxime. Thus, oxime 1, a structural analogue of a triarylethylene estrogen, showed a significant binding affinity for the ER. The OH of the oxime function appears to mimic the phenolic OH present in more "classical" ER ligands because the binding reduced when the oxime OH is methylated (2) or absent (3).

  DOI：

  10.1021/jm010948j
• 作为产物：
  描述：

  3,4-二氯-2-羟基苯甲醛 在 对甲苯磺酸 tris(dibenzylideneacetone)dipalladium (0) 、 caesium carbonate 、 三环己基膦 作用下， 以 1,4-二氧六环 、 甲苯 、 苯 为溶剂， 反应 56.0h， 生成 3,4-Diphenylsalicylaldehyde
  参考文献：
  名称：

  Salicylaldoxime Moiety as a Phenolic “A-Ring” Substitute in Estrogen Receptor Ligands

  摘要：

  The phenolic "A-ring" of natural and synthetic estrogen receptor (ER) ligands was effectively replaced by a planar six-member ring formed through an intramolecular hydrogen bond within a salicylaldoxime. Thus, oxime 1, a structural analogue of a triarylethylene estrogen, showed a significant binding affinity for the ER. The OH of the oxime function appears to mimic the phenolic OH present in more "classical" ER ligands because the binding reduced when the oxime OH is methylated (2) or absent (3).

  DOI：

  10.1021/jm010948j

文献信息

• Salicylideneaniline/Dithienylethene Hybrid Molecular Switches: Design, Synthesis, and Photochromism
  作者：Péter Pál Kalapos、Attila Kunfi、Marcell M. Bogner、Tamás Holczbauer、Michał Andrzej Kochman、Bo Durbeej、Gábor London

  DOI：10.1021/acs.joc.3c00828

  日期：2024.1.5

  reported. Due to an interplay between solvent-assisted enol–keto tautomerization in the former moiety and photochromic electrocyclization in the latter, this dithienylbenzene derivative was found to be photoresponsive at room temperature with a thermally stable closed form. The main photoproduct featuring ring-closed DTE and keto-enamine SA structures could be isolated and converted back to the starting

  报道了一种混合分子开关，其包含围绕单个苯环的水杨基苯胺（SA）和二噻吩乙烯（DTE）部分。由于前者的溶剂辅助烯醇-酮互变异构与后者的光致变色电环化之间的相互作用，这种二噻吩基苯衍生物被发现在室温下具有光响应性，具有热稳定的闭合形式。主要光产物具有闭环 DTE 和酮-烯胺 SA 结构，可以通过可见光照射分离并转化回起始材料。通过使用密度泛函理论（DFT）计算来表征整个过程中涉及的潜在结构的光学性质，与测量数据非常吻合。转化的可逆性可以通过供体和受体取代基的存在来调节，而以苯并噻唑部分形式引入的亚胺甚至可以在非质子溶剂中实现光化学。
• Salicylaldoxime Moiety as a Phenolic “A-Ring” Substitute in Estrogen Receptor Ligands
  作者：Filippo Minutolo、Simone Bertini、Chiara Papi、Kathryn E. Carlson、John A. Katzenellenbogen、Marco Macchia

  DOI：10.1021/jm010948j

  日期：2001.11.1

  The phenolic "A-ring" of natural and synthetic estrogen receptor (ER) ligands was effectively replaced by a planar six-member ring formed through an intramolecular hydrogen bond within a salicylaldoxime. Thus, oxime 1, a structural analogue of a triarylethylene estrogen, showed a significant binding affinity for the ER. The OH of the oxime function appears to mimic the phenolic OH present in more "classical" ER ligands because the binding reduced when the oxime OH is methylated (2) or absent (3).