4-bromo-1-(4-bromophenyl)-1H-pyrazole-3-ol | 543694-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-bromo-1-(4-bromophenyl)-1H-pyrazole-3-ol
• 英文别名: 4-bromo-1-(4-bromophenyl)-3-hydroxy-1H-pyrazole；4-bromo-1-(4-bromophenyl)-1H-pyrazol-3-ol；4-bromo-2-(4-bromophenyl)-1H-pyrazol-5-one
• CAS: 543694-92-4
• 化学式: C₉H₆Br₂N₂O
• 分子量: 317.967
• InChiKey: OOXXDCAEYMZUBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴己烷 、 4-bromo-1-(4-bromophenyl)-1H-pyrazole-3-ol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以95%的产率得到4-bromo-1-(4-bromophenyl)-3-hexyloxy-1H-pyrazole
  参考文献：
  名称：

  Pyrazolyl-substituted polyconjugated molecules for optoelectronic applications

  摘要：

  Pyrazolyl-substituted diethylene derivative and its analogue containing additional cyano groups were synthesized and investigated as potential multifunctional materials for organic light emitting diodes. The influence of the electron affinitive cyano groups on the ionization potential (I-p) of the films as well as on the photoluminescence (PL) spectrum, PL quantum yield (eta) and PL decay time of the dilute solutions and thin films of the pyrazole derivatives was studied. PL measurements revealed that highly luminescent (eta = 0.88) cyano-free pyrazole derivative in solution became non-emissive (eta = 0.01) by attaching cyano groups as a result of these groups-induced torsional deactivation. However in the solid state, the steric and electrostatic effects of the bulky and polar cyano groups prevented tight packing of the pyrazole derivative molecules, thus significantly reducing migration-induced quenching of the excitons at the defects. Incorporation of the cyano groups resulted in the two-fold enhancement of the PL quantum yield in the film of the pyrazole derivative as compared to that of the cyano-free film. The I-p of 5.90 eV estimated for the cyano groups-containing compound was found to be higher as compared to the I-p of 5.46 eV for cyano-free analogue, what in conjunction with the PL data for the films indicates increased electron affinity in the pyrazole derivative with additional cyano groups. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.10.007
• 作为产物：
  描述：

  1-苯基-1,5-二氢-4H-咪唑-4-酮 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 19.0h， 以82%的产率得到4-bromo-1-(4-bromophenyl)-1H-pyrazole-3-ol
  参考文献：
  名称：

  钯催化卤代1-苯基吡唑-3-醇与相关三氟甲磺酸酯的交叉偶联反应

  摘要：

  1-苯基-1 H-吡唑-3-醇被用作通用的合成子，用于制备在吡唑核的C-3和C-4以及在苯环上取代的各种1-苯基-1 H-吡唑衍生物对位。在碱存在下用三氟甲磺酸酐处理1-苯基-1 H-吡唑-3-醇，得到3-三氟甲酰氧基吡唑，而溴化和碘化则得到相应的卤代衍生物。获得的支架用于碳-碳键形成的Pd催化的交叉偶联反应中，生成（杂）芳基和碳官能取代的1-苯基-1 H-吡唑。

  DOI：

  10.1016/j.tet.2009.07.017

文献信息

• A novel one-pot approach to oxidative aromatization and bromination of pyrazolidin-3-one with HBr-H₂O₂ system
  作者：Shanguang Yang、Jingjing Liu、Zhudan Jin、Wei Tian、Hao Sun、Mingliang Wang

  DOI：10.1515/hc-2018-0046

  日期：2018.6.27

  Abstract An efficient and green one-pot method for the oxidative aromatization and bromination of pyrazolidin-3-ones under mild conditions with a HBr-H2O2 system was developed. A mechanism was proposed.

  摘要 开发了一种高效、绿色的一锅法，在温和条件下，采用 HBr-H2O2 体系进行吡唑啉-3-酮的氧化芳构化和溴化。提出了一种机制。
• 一种制备4-溴代N-芳基吡唑类化合物的工艺
  申请人：曲靖师范学院

  公开号：CN114874144A

  公开（公告）日：2022-08-09

  本方案公开一种制备4‑溴代N‑芳基吡唑类化合物的工艺：在有机溶剂二甲基亚砜(DMSO)中，以N‑芳基‑3‑吡唑烷酮类化合物为原料，与N‑溴代丁二酰亚胺(NBS)在空气、95～105℃加热条件下反应制得4‑溴代N‑芳基吡唑类化合物。
• COMPOUNDS THAT INHIBIT HUMAN DNA LIGASES AND METHODS OF TREATING CANCER
  申请人：TOMKINSON Alan E.

  公开号：US20100099683A1

  公开（公告）日：2010-04-22

  Methods for treating cancer using compounds that inhibit human DNA ligases. Methods for using compounds that inhibit human DNA ligases to provide insights into the reaction mechanisms of human DNA ligases, for example to identify the human DNA ligase involved in different DNA repair pathways. Screening methods for compounds that inhibit human DNA ligases.
• Compounds that inhibit human DNA ligases and methods of treating cancer
  申请人：University of Maryland, Baltimore

  公开号：US20140113891A1

  公开（公告）日：2014-04-24

  Methods for treating cancer using compounds that inhibit human DNA ligases. Methods for using compounds that inhibit human DNA ligases to provide insights into the reaction mechanisms of human DNA ligases, for example to identify the human DNA ligase involved in different DNA repair pathways. Screening methods for compounds that inhibit human DNA ligases.
• US8445537B2
  申请人：——

  公开号：US8445537B2

  公开（公告）日：2013-05-21