(2-bromophenyl)(2-hydroxy-5-methylphenyl)methanone | 55270-73-0

• 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: (2-bromophenyl)(2-hydroxy-5-methylphenyl)methanone
• 英文别名: 2'-bromo-2-hydroxy-5-methyl-benzophenone；2'-Brom-2-hydroxy-5-methyl-benzophenon；(2-bromophenyl)-(2-hydroxy-5-methylphenyl)methanone
• CAS: 55270-73-0
• 化学式: C₁₄H₁₁BrO₂
• 分子量: 291.144
• InChiKey: UZYBBFDHCJUIRS-UHFFFAOYSA-N

物化性质

• 熔点：
  78°C5
• 沸点：
  387.7±32.0 °C(Predicted)
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (2-bromophenyl)(2-hydroxy-5-methylphenyl)methanone 在 potassium carbonate 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 13.0h， 生成 2-[2-(2-bromobenzoyl)-4-methylphenoxypropyl]-5-ethylmercaptoacetate-[1,3,4] oxadiazole
  参考文献：
  名称：

  设计，合成与恶二唑硫桥吡唑药效基团偶联的二苯甲酮作为抗炎和止痛药。

  摘要：

  前列腺素（PG）是一组具有多种激素样作用的生理活性脂质化合物，是人体对疼痛和炎症反应的重要介体，由细胞膜中的必需脂肪酸形成。该反应由环氧合酶催化，环氧合酶是一种与膜相关的酶，以两种同工型COX-1和COX-2发生。非甾体类抗炎药（NSAIDs）通过抑制COX的活性发挥作用。鉴于此，设计，合成，表征并随后评价了与恶二唑硫桥吡唑部分8a-1缀合的一系列新型二苯甲酮的抗炎和镇痛特性。新型类似物8a-1的研究对潜在的抗炎活性显示出高水平的COX-1和COX-2抑制活性。在该系列中，化合物8i在二苯甲酮的苯甲酰基环的对位具有吸电子氟基团，其特征在于对COX-1和COX-2的抑制均具有最高的IC 50值，这与标准药物相当。此外，已经对有效化合物进行了分子对接研究。

  DOI：

  10.1016/j.bioorg.2019.103220
• 作为产物：
  描述：

  2-bromo-benzoic acid p-tolyl ester 在 三氯化铝 作用下， 以 硝基苯 为溶剂， 以70%的产率得到(2-bromophenyl)(2-hydroxy-5-methylphenyl)methanone
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of benzophenone analogues

  摘要：

  A series of substituted benzophenone analogues has been synthesized and evaluated as orally active anti-inflammatory agents with reduced side effects. The anti-inflammatory and ulcerogenic activities of the compounds were compared with naproxen, indomethacin, and phenylbutazone. In carrageenan-induced foot pad edema assay, benzophenone analogues showed an interesting anti-inflammatory activity. In the air-pouch test, some of the analogues reduced the total number of leukocytes of the exudate, which indicates inhibition of prostaglandin production. Side effects of the compounds were examined on gastric mucosa, in the liver and stomach. None of the compounds showed significant side effects compared with nonsteroidal anti-inflammatory drugs such as indomethacin and naproxen. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.04.003

文献信息

• Synthesis and tumor inhibitory activity of novel coumarin analogs targeting angiogenesis and apoptosis
  作者：B.R. Vijay Avin、Prabhu Thirusangu、V. Lakshmi Ranganatha、Aiyesha Firdouse、B.T. Prabhakar、Shaukath Ara Khanum

  DOI：10.1016/j.ejmech.2014.01.050

  日期：2014.3

  A sequence of coumarin analogs 5a–j was obtained by multi step synthesis from hydroxy benzophenones (1a–j). The in vitro antiproliferative effect of the title compounds was tested against Ehrlich ascites carcinoma (EAC) and Daltons lymphoma ascites (DLA) cell lines. Among the series, compound 5c with bromo group in the benzophenone moiety was endowed with excellent antiproliferative potency with significant

  通过多步合成从羟基二苯甲酮（1a – j）获得了香豆素类似物5a – j的序列。在体外的标题化合物的抗增殖作用是对艾氏腹水癌（EAC）和道尔顿淋巴瘤腹水（DLA）细胞系进行测试。在该系列中，在二苯甲酮部分中具有溴基的化合物5c具有出色的抗增殖潜能，IC 50值很高。此外，化合物5c对鼠EAC和实体DL肿瘤模型系统的体内抗肿瘤作用通过延长的存活期得到证实。复方的抑瘤机制5c是由于抗血管生成和促进细胞凋亡。这些结果表明化合物5c的可能应用，其可以在不久的将来被开发为有效的抗癌药。
• An efficient copper-catalytic system for performing intramolecular O-arylation reactions in aqueous media. New synthesis of xanthones
  作者：Nekane Barbero、Raul SanMartin、Esther Domínguez

  DOI：10.1039/b900931k

  日期：——

  A safe, efficient protocol for the copper-catalysed intramolecular O-arylation of 2-halobenzophenones on water to afford the valuable xanthone framework is reported. The recovery and the successful reutilization of the aqueous solution containing the copper catalyst are also presented. Moreover, the scalability and the easy setup and purification tasks of this sustainable method make it appealing for bulk industry applications.

  报道了一种安全、高效的铜催化2-卤代苯基酮在水中进行分子内O-芳基化的协议，以获得具有价值的黄酮框架。同时，本文还介绍了含铜催化剂的水相溶液的回收和成功再利用。此外，该可持续方法的可扩展性以及简便的搭建和纯化过程，使其在大规模工业应用中具有吸引力。
• Meisenheimer; Hanssen; Waechterowitz, Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 119, p. 351
  作者：Meisenheimer、Hanssen、Waechterowitz

  DOI：——

  日期：——
• Synthesis and evaluation of in vitro antimicrobial activity of novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles
  作者：V. Girish、Noor Fatima Khanum、H. D. Gurupadaswamy、Shaukath Ara Khanum

  DOI：10.1134/s1068162014030066

  日期：2014.5

  Synthetic pathway of the ten novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles as new potential antimicrobial agents is illustrated. Intramolecular cyclization of 2-(2-aroylaryloxy) aceto hydrazides to 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles was achieved with triethyl orthoformate in good yields. The compounds were characterized by IR, H-1 NMR, mass spectra and by means of CHN analysis. The target compounds were tested for their in vitro antimicrobial activity against representative strains by disc diffusion method and micro dilution methods. Several compounds showed antimicrobial activity comparable with or higher than the standard drugs.
• Rosenmund; Schnurr, Justus Liebigs Annalen der Chemie, 1928, vol. 460, p. 89
  作者：Rosenmund、Schnurr

  DOI：——

  日期：——