双(5-溴-2-羟基苯基)甲酮 | 82845-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 双(5-溴-2-羟基苯基)甲酮
• 英文名称: 5,5'-dibromo-2,2'-dihydroxy-benzophenone
• 英文别名: 5,5'-Dibrom-2,2'-dihydroxy-benzophenon；Bis(5-bromo-2-hydroxyphenyl)methanone
• CAS: 82845-53-2
• 化学式: C₁₃H₈Br₂O₃
• 分子量: 372.013
• InChiKey: VRLIJNKTPYPWQI-UHFFFAOYSA-N

物化性质

• 沸点：
  430.8±45.0 °C(Predicted)
• 密度：
  1.890±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  双(5-溴-2-羟基苯基)甲酮 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-[2'-hydroxy-4'-bromophenyl]-5-bromo-1,2-benzisoxazole
  参考文献：
  名称：

  杂环合成中的氧杂蒽酮。一种合成 C-3 邻羟基芳基取代的 1,2-苯并异恶唑及其 N-氧化物、血管紧张素 (II) 拮抗剂杂合肽的潜在支架的有效途径

  摘要：

  Regioselective substitution of xanthone and its nucleophilic cleavage allow the synthesis of C-3 o-hydroxyaryl substituted 1,2-benzisoxazoles or their N-oxides by cyclodehydration or oxidative cyclization of their corresponding ketoxime precursors, respectively. Molecular modeling analysis and H-1 NMR spectra indicate an intramolecular H-bonding engaging phenol OH and the isoxazole ring N atom.

  DOI：

  10.3987/com-11-12162
• 作为产物：
  描述：

  占吨酮 在 溴 、 溶剂黄146 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 28.0h， 生成 双(5-溴-2-羟基苯基)甲酮
  参考文献：
  名称：

  双(2-羟苯基)甲酮和麦德鲁姆酸通过羟醛反应/双内酯化级联反应合成V型双香豆素

  摘要：

  使用容易获得的双（2-羟基苯基）甲酮和 Meldrum 酸，开发了一种用于合成色烯[3,4-c]色烯-6,7-二酮的简洁有效的方法。该协议显示了广泛的底物范围和良好的官能团耐受性，包括烷基、烷氧基、芳基和卤素。这些 π 延伸的支架显示出具有大斯托克斯位移的蓝绿色荧光。光物理研究表明，2 位取代的色烯[3,4-c]色烯-6,7-二酮引起了显着的红移。

  DOI：

  10.1002/ejoc.202101489

文献信息

• Rh-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones
  作者：Maddali L. N. Rao、Boddu S. Ramakrishna

  DOI：10.1039/c6ra18647e

  日期：——

  An efficient rhodium-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones was developed from functionalized salicylaldehydes. This approach provides an easy access to various functionalized 2,2′-dihydroxybenzophenone and xanthone core skeletons. This study also revealed the crucial role of the hydroxy group in the reductive homo-coupling process to generate 2,2′-dihydroxybenzophenones

  从功能化的水杨醛开发了有效的铑催化直接合成2,2'-二羟基二苯甲酮和氧杂蒽。这种方法可以轻松访问各种功能化的2,2'-二羟基二苯甲酮和黄酮核心骨架。这项研究还揭示了羟基在生成2,2'-二羟基二苯甲酮的还原均偶联过程中的关键作用。总的来说，还发现反应过程的结果受到水杨醛中取代基的电子学的影响。
• Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade
  作者：Shenci Lu、Jun-Yang Ong、Hui Yang、Si Bei Poh、Xi Liew、Chwee San Deborah Seow、Ming Wah Wong、Yu Zhao

  DOI：10.1021/jacs.9b08510

  日期：2019.10.30

  We present herein an unprecedented stereoselective synthesis of bridged biaryls with defined axial and central chirality from readily available starting materials. This N-heterocyclic carbene-catalyzed method proceeds through propargylic substitution of azolium enolates followed by two-directional cyclization, as supported by DFT calculation. A range of benzofuran/indole-derived bridged biaryls bearing an eight-membered lactone are accessed with uniformly high stereoselectivity (>98:2 dr, mostly >98% ee).
• Xanthones in Heterocyclic Synthesis. An Efficient and General Route for the Synthesis of Regioselectively Substituted Phthalazines
  作者：Petros G. Tsoungas、Paul Cordopatis、Yiannis Gardikis、Constantinos Potamitis、Maria Zervou、George Pairas

  DOI：10.3987/com-11-12168

  日期：——

  Xanthone undergoes regioselective substitution and nucleophically triggered ring opening to the corresponding ketone. Hydrazone of the latter oxidatively rearranges to ortho-diacylarenes, which, then, with hydrazine gives regioselectively substituted phthalazines. Molecular modeling analysis and H-1 NMR spectra indicate an intramolecular H-bonding engaging phenol OH and phthalazine N-3 atom.
• Diels; Rosenmund, Chemische Berichte, 1906, vol. 39, p. 2362
  作者：Diels、Rosenmund

  DOI：——

  日期：——
• 2,2′-Dihydroxybenzophenones and their carbonyl N-analogues as inhibitor scaffolds for MDR-involved human glutathione transferase isoenzyme A1-1
  作者：Fereniki D. Perperopoulou、Petros G. Tsoungas、Trias N. Thireou、Vagelis E. Rinotas、Eleni K. Douni、Elias E. Eliopoulos、Nikolaos E. Labrou、Yannis D. Clonis

  DOI：10.1016/j.bmc.2014.06.007

  日期：2014.8

  The MDR-involved human GSTA1-1, an important isoenzyme overexpressed in several tumors leading to chemotherapeutic-resistant tumour cells, has been targeted by 2,2'-dihydroxybenzophenones and some of their carbonyl N-analogues, as its potential inhibitors. A structure-based library of the latter was built-up by a nucleophilic cleavage of suitably substituted xanthones to 2,2'-dihydroxy-benzophenones (5-9) and subsequent formation of their N-derivatives (oximes 11-13 and N-acyl hydrazones 14-16). Screening against hGSTA1-1 led to benzophenones 6 and 8, and hydrazones 14 and 16, having the highest inhibition potency (IC₅₀ values in the range 0.18 ± 0.02 to 1.77 ± 0.10 μM). Enzyme inhibition kinetics, molecular modeling and docking studies showed that they interact primarily at the CDNB-binding catalytic site of the enzyme. In addition, the results from cytotoxicity studies with human colon adenocarcinoma cells showed low LC₅₀ values for benzophenone 6 and its N-acyl hydrazone analogue 14 (31.4 ± 0.4 μM and 87 ± 1.9 μM, respectively), in addition to the strong enzyme inhibition profile (IC₅₀(6)=1,77 ± 0.10 μM; IC₅₀(14)=0.33 ± 0.05 μM). These structures may serve as leads for the design of new potent mono- and bi-functional inhibitors and pro-drugs against human GTSs.