2,5-dihydroxybenzaldehyde oxime | 37110-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,5-dihydroxybenzaldehyde oxime
• 英文别名: 2,5-Dihydroxybenzaldoxim；2-(hydroxyiminomethyl)benzene-1,4-diol
• CAS: 37110-11-5
• 化学式: C₇H₇NO₃
• 分子量: 153.137
• InChiKey: XHBLHEQHMFWIIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C
• 沸点：
  369.1±32.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• 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：

  2,5-dihydroxybenzaldehyde oxime 在 盐酸 、 methyl orange 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 2-[(Hydroxyamino)methyl]benzene-1,4-diol
  参考文献：
  名称：

  Synthesis and tyrosinase inhibitory activity of novel N-hydroxybenzyl-N-nitrosohydroxylamines

  摘要：

  Several novel N-substituted N-nitrosohydroxylamines were synthesized. They all inhibited mushroom tyrosinase, but the type of inhibition was different depending on the substituent. Some N-(mono- or dihydroxybenzyl)-N-nitrosohydroxylamines exhibited uncompetitive inhibition with respect to (L)-dopa. Among them, compound 6 was also a competitive inhibitor with respect to oxygen. This observation suggests that another interaction by the meta- or para-hydroxyl group might stabilize the binding of the inhibitor to the enzyme through the oxygen binding site. (C) 2003 Elsevier Science (USA). All rights reserved.

  DOI：

  10.1016/s0045-2068(03)00026-9
• 作为产物：
  描述：

  2,5-二羟基苯甲醛 在 盐酸羟胺 、 potassium carbonate 作用下， 以 水 为溶剂， 以15%的产率得到2,5-dihydroxybenzaldehyde oxime
  参考文献：
  名称：

  具有强效抗结核分枝杆菌活性的简单芳基肟和硝基呋喃衍生物的合成和合成孔径雷达研究

  摘要：

  背景：肟和硝基呋喃基衍生物是药物化学中特别重要的化合物。因此，据报道，许多研究人员具有抗菌、抗寄生虫、杀虫和杀真菌活性。方法：在这项工作中，我们报告了一系列五十种芳基肟 ArCH=N-OH, I 和八种硝基呋喃基化合物 2-硝基呋喃基-X, II 的合成和抗结核分枝杆菌 H37RV 的生物活性。结果：在肟中，I：Ar = 2-OH-4-OH，42 和 I：Ar = 5-硝基呋喃基，46，分别在 3.74 和 32.0 µM 处具有最佳活性。还有，46，硝基呋喃化合物，II；X = MeO，55 和 II：X = NHCH2Ph，58，（分别为 14.6 和 12.6 µM），表现出优异的生物活性并且无细胞毒性。结论：化合物55显示出9.85的选择性指数。使用化合物 55 进行了进一步的抗菌测试，该化合物对粪肠球菌、肺炎克雷伯菌、铜绿假单胞菌、金黄色葡萄球菌、鼠伤寒沙门氏菌和福氏志贺氏菌无活

  DOI：

  10.2174/1570180816666181227115738

文献信息

• Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides
  作者：Jinyi Song、Hongyan Zhao、Yang Liu、Huatao Han、Zhuofei Li、Wenyi Chu、Zhizhong Sun

  DOI：10.1039/c6nj02815b

  日期：——

  synthesized using the Vilsmeier–Haack reaction and oximation. 2,5-Dihydroxyterephthalaldehyde dioxime (L8) as an efficient N,O-symmetrical bidentate ligand was prepared from hydroquinone. It was studied as a high activity ligand for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions. The coupling reactions were performed in the presence

  使用Vilsmeier-Haack反应和肟化合成了一系列N，O-双齿配体。由对苯二酚制备作为有效的N，O-对称双齿配体的2，5-二羟基对苯甲醛二肟（L 8）。作为温和条件下芳基氯化物与芳基硼酸的钯催化的Suzuki-Miyaura交叉偶联反应的高活性配体，已对其进行了研究。偶联反应在PdCl 2作为催化剂，L 8作为配体，Na 2 CO 3存在下进行在85°C下，PEG-400作为PTC，在乙醇/水（1：1）中作为对环境无害的溶剂。通过优化的反应在0.20 mol％的低钯负载下以良好的收率获得了大量的联芳基。
• [60]Fullerene Adducts with Improved Electron Acceptor Properties
  作者：Beatriz M. Illescas、Nazario Martín

  DOI：10.1021/jo0003753

  日期：2000.9.1

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.
• Synthesis and SAR Study of Simple Aryl Oximes and Nitrofuranyl Derivatives with Potent Activity Against Mycobacterium tuberculosis
  作者：Cristiane França da Costa、Marcus Vinicius Nora de Souza、Maria Cristina da Silva Lourenço、Elaine Soares Coimbra、Guilherme da Silva Lourenço Carvalho、James Wardell、Stephane Lima Calixto、Juliana da Trindade Granato

  DOI：10.2174/1570180816666181227115738

  日期：2019.12.31

  Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight

  背景：肟和硝基呋喃基衍生物是药物化学中特别重要的化合物。因此，据报道，许多研究人员具有抗菌、抗寄生虫、杀虫和杀真菌活性。方法：在这项工作中，我们报告了一系列五十种芳基肟 ArCH=N-OH, I 和八种硝基呋喃基化合物 2-硝基呋喃基-X, II 的合成和抗结核分枝杆菌 H37RV 的生物活性。结果：在肟中，I：Ar = 2-OH-4-OH，42 和 I：Ar = 5-硝基呋喃基，46，分别在 3.74 和 32.0 µM 处具有最佳活性。还有，46，硝基呋喃化合物，II；X = MeO，55 和 II：X = NHCH2Ph，58，（分别为 14.6 和 12.6 µM），表现出优异的生物活性并且无细胞毒性。结论：化合物55显示出9.85的选择性指数。使用化合物 55 进行了进一步的抗菌测试，该化合物对粪肠球菌、肺炎克雷伯菌、铜绿假单胞菌、金黄色葡萄球菌、鼠伤寒沙门氏菌和福氏志贺氏菌无活
• Synthesis and tyrosinase inhibitory activity of novel N-hydroxybenzyl-N-nitrosohydroxylamines
  作者：Mitsuhiro Shiino、Yumi Watanabe、Kazuo Umezawa

  DOI：10.1016/s0045-2068(03)00026-9

  日期：2003.4

  Several novel N-substituted N-nitrosohydroxylamines were synthesized. They all inhibited mushroom tyrosinase, but the type of inhibition was different depending on the substituent. Some N-(mono- or dihydroxybenzyl)-N-nitrosohydroxylamines exhibited uncompetitive inhibition with respect to (L)-dopa. Among them, compound 6 was also a competitive inhibitor with respect to oxygen. This observation suggests that another interaction by the meta- or para-hydroxyl group might stabilize the binding of the inhibitor to the enzyme through the oxygen binding site. (C) 2003 Elsevier Science (USA). All rights reserved.