2,4-Dihydroxy-benzophenon-oxim | 50593-96-9

• 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: 2,4-Dihydroxy-benzophenon-oxim
• 英文别名: 3-Hydroxy-4-[(hydroxyamino)(phenyl)methylidene]cyclohexa-2,5-dien-1-one；4-(N-hydroxy-C-phenylcarbonimidoyl)benzene-1,3-diol
• CAS: 50593-96-9
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: RQMFMNVYRBQXKO-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  453.1±28.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-Dihydroxy-benzophenon-oxim 在 吡啶 、 三氯化铝 作用下， 反应 3.58h， 生成 1-(6-Hydroxy-3-phenyl-1,2-benzoxazol-7-yl)ethanone
  参考文献：
  名称：

  Rao, E. V. S. Bhushana; Kumari, S. Subhadra; Rao, K. S. R. Krishna Mohan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 620 - 623

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二羟二苯甲酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 反应 6.0h， 以89.8%的产率得到2,4-Dihydroxy-benzophenon-oxim
  参考文献：
  名称：

  发现一类新的苯并恶唑衍生物作为组胺 H3 受体配体用于治疗神经性疼痛

  摘要：

  为了发现有效的镇痛剂，我们总结了一系列针对 H 3受体 (H 3 R)的新型苯并恶唑衍生物的合成、优化和药理学抗伤害作用。在体外测定了新的苯并恶唑的组胺H 3 R 和H 1 R 结合亲和力。最佳化合物8d (2-methyl-6-(3-(4-methylpirazin-1-yl)propoxy)benzo[d]oxazole) 对 H 3 R ( K i = 19.7 nM) 表现出高亲和力，对 10其他脱靶受体，对人类 ether-a-go-go 相关基因（hERG，心脏离子通道）的影响可以忽略不计。在啮齿动物中，化合物8d剂量依赖性地逆转福尔马林诱发的疼痛（I 期，ED 50 = 6.0 mg/kg；II 期，ED 50 = 7.8 mg/kg）和 CCI 诱导的神经性疼痛（慢性缩窄性损伤，ED 50 = 15.6 mg/kg） . 此外，化合物8d在急性毒性试验（LD 50 > 2000

  DOI：

  10.1016/j.bioorg.2022.106039

文献信息

• Efficient Synthesis of 2-Substituted Benzoxazoles via Beckmann Rearrangement of 2-Hydroxyaryl Ketoximes Using Diethyl Chlorophosphate
  作者：A. Sardarian、Z. Shahsavari-Fard

  DOI：10.1055/s-2008-1072767

  日期：2008.5

  An efficient method for synthesis of 2-substituted benz-oxazoles has been developed using diethyl chlorophosphate. 2-Hydroxyaryl ketoximes are efficiently converted to benzoxazoles by heating in the presence of diethyl chlorophosphate via Beckmann rearrangement of ketoxime in excellent yields. This method avoids the use of strong acids, harsh conditions, and long reaction times.

  已开发出一种使用氯磷酸二乙酯合成 2-取代苯并恶唑的有效方法。2-羟基芳基酮肟通过在氯磷酸二乙酯存在下加热，通过酮肟的贝克曼重排以优异的产率有效转化为苯并恶唑。这种方法避免了使用强酸、苛刻的条件和较长的反应时间。
• Synthesis and Aminomethylation of 3-Substituted 6-Hydroxy-1,2-Benzisoxazoles
  作者：M. S. Frasinyuk

  DOI：10.1007/s10593-014-1631-z

  日期：2015.2

  Oximes of 2,4-dihydroxybenzophenones, 1-(2,4-dihydroxyphenyl)-2-phenylethanones, and 1-(2,4-di-hydroxyphenyl)-2-phenoxyethanones were dehydrated with 1,1'-carbonyldiimidazole, yielding 3-substi-tuted 6-hydroxy-1,2-benzisoxazoles, aminomethylation reactions of which were studied with various reagents.
• Synthesis, characterization, DNA interaction and cleavage activity of new mixed ligand copper(II) complexes with heterocyclic bases
  作者：M.S. Surendra Babu、K. Hussain Reddy、Pitchika G. Krishna

  DOI：10.1016/j.poly.2006.08.026

  日期：2007.2

  Mixed ligand complexes having the formulae Cu(RPO)(2)PY2, Cu(RPO)(2)Im(2), and Cu(DBO)(2)Py-2 [RPO = resacetophenone oxime, DBO = 2,4-dihydroxybenzophenone oxime, Py = pyridine and Ina = imidazole] have been synthesized and characterized by UV-Vis, IR, ESR, cyclic voltammetry and magnetic susceptibility methods. Absorption studies revealed that each of these octahedral complexes is an avid binder of calf thymus DNA. The apparent binding constants for mixed ligand complexes are in order of 10(4)-10(5) M-1. Based on the data obtained in the DNA binding studies a partial intercalative mode of binding is suggested for these complexes. The nucleolytic cleavage activity of the adducts was carried out on double stranded pBR322 circular plasmid DNA by using a gel electrophoresis experiment in the presence and absence of oxidant (H2O2). All the metal complexes cleaved supercoiled DNA by hydrolytic and oxidative paths. The oxidative path dominates the hydrolytic cleavage. The hydrolytic cleavage of DNA is evidenced from the control experiments showing discernable cleavage inhibition in the presence of the hydroxyl radical inhibitor DMSO or the singlet oxygen quencher azide ion. (c) 2006 Elsevier Ltd. All rights reserved.
• Triflic Anhydride: A Mild Reagent for Highly Efficient Synthesis of 1,2-Benzisoxazoles, Isoxazolo, and Isothiazolo Quinolines Without Additive or Base
  作者：Rajesh G. Kalkhambkar、H. Yuvaraj

  DOI：10.1080/00397911.2013.821617

  日期：2014.2.16

  The synthetic utility of trifluoromethanesulphonic anhydride (triflic anhydride, TA) without additive or base for the high-yielding synthesis of a wide variety of 1,2-benzisoxazoles from 2-hydroxyaryl aldoximes and ketoximes under mild conditions has been carried out for the first time. As a continuation of our study, syntheses of isoxazolo and isothiazolo quinolones have also been demonstrated using triflic anhydride under similar conditions. This method is simple and has benefits from the easy way to isolate the products in excellent yields. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• Rao, E. V. S. Bhushana; Kumari, S. Subhadra; Rao, K. S. R. Krishna Mohan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 620 - 623
  作者：Rao, E. V. S. Bhushana、Kumari, S. Subhadra、Rao, K. S. R. Krishna Mohan

  DOI：——

  日期：——