2,5-二羟基-N-(2-羟乙基)苯甲酰胺 | 61969-53-7

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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: 2,5-二羟基-N-(2-羟乙基)苯甲酰胺
• 中文别名: 龙胆酸乙醇胺；2,4-二氢-5-(4-甲基苯基)-3H-吡唑-3-酮
• 英文名称: 2,5-dihydroxy-N-(2-hydroxyethyl)benzamide
• CAS: 61969-53-7
• 化学式: C₉H₁₁NO₄
• mdl: MFCD00128117
• 分子量: 197.191
• InChiKey: YNCOLLPSNIHBGO-UHFFFAOYSA-N

物化性质

• 熔点：
  145-148 °C
• 沸点：
  466.6±45.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)
• 溶解度：
  0.29 M

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

制备方法与用途

用途：用于重氮偶合剂、硫化剂和感光剂等。

反应信息

• 作为反应物：
  描述：

  2,5-二羟基-N-(2-羟乙基)苯甲酰胺 在 氯化亚砜 、 碳酸氢钠 作用下， 生成 2-(2-oxazolin-2-yl)benzene-1,4-diol
  参考文献：
  名称：

  2-(2-Oxazolin-2-yl)benzene-1,4-diol: X-ray and density functional theory studies

  摘要：

  In the crystal structure of the title compound, C9H9NO3, there are strong intramolecular O-H center dot center dot center dot N and intermolecular O-H center dot center dot center dot O hydrogen bonds which, together with weak intermolecular C-H center dot center dot center dot O hydrogen bonds, lead to the formation of in nite chains of molecules. The calculated intermolecular hydrogen-bond energies are -11.3 and -2.7 kJ mol(-1), respectively, showing the dominant role of the O-H center dot center dot center dot O hydrogen bonding. A natural bond orbital analysis revealed the electron contribution of the lone pairs of the oxazoline N and O atoms, and of the two hydroxy O atoms, to the order of the relevant bonds.

  DOI：

  10.1107/s0108270107004131
• 作为产物：
  描述：

  2,5-二羟基苯甲酸甲酯 、 C.I.酸性橙108 生成 2,5-二羟基-N-(2-羟乙基)苯甲酰胺
  参考文献：
  名称：

  US2463462

  摘要：

  公开号：

文献信息

• Nuclear Amination Catalyzed by Fungal Laccases:  Reaction Products of <i>p</i>-Hydroquinones and Primary Aromatic Amines
  作者：Timo H. J. Niedermeyer、Annett Mikolasch、Michael Lalk

  DOI：10.1021/jo048454s

  日期：2005.3.1

  amination of p-hydroquinones with primary aromatic amines was catalyzed by fungal laccases (EC 1.10.3.2) from Trametes spec. and Myceliophthora thermophila. This is the first report of laccase-catalyzed synthesis of aminoquinones. Incubation of two compounds with laccase in the presence of oxygen resulted in the formation of the corresponding monoaminated or diaminated quinones. No hydroquinonoids were formed

  Trametes spec。的真菌漆酶（EC 1.10.3.2）催化了对羟基苯醌与伯芳族胺的核胺化反应。和嗜热毁丝霉菌。这是漆酶催化合成氨基醌的首次报道。在氧气存在下将两种化合物与漆酶一起孵育会导致形成相应的单胺化或二价苯醌。没有形成氢醌类化合物。讨论了在不同的对氢醌和芳香胺与不同的漆酶反应过程中观察到的差异。
• Novel Cephalosporins Synthesized by Amination of 2,5-Dihydroxybenzoic Acid Derivatives Using Fungal Laccases II
  作者：Annett Mikolasch、Timo Horst Johannes Niedermeyer、Michael Lalk、Sabine Witt、Simone Seefeldt、Elke Hammer、Frieder Schauer、Manuela Gesell Salazar、Susanne Hessel、Wolf-Dieter J&uuml;lich、Ulrike Lindequist

  DOI：10.1248/cpb.55.412

  日期：——

  Sixteen novel cephalosporins were synthesized by amination of 2,5-dihydroxybenzoic acid derivatives with the aminocephalosporins cefadroxil, cefalexin, cefaclor, and the structurally related carbacephem loracarbef using laccases from Trametes sp. or Myceliophthora thermophila. All products inhibited the growth of several Gram positive bacterial strains in the agar diffusion assay, among them methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci. The products protected mice against an infection with Staphylococcus aureus lethal to the control animals. Cytotoxicity and acute toxicity of the new compounds were negligible. The results show the usefulness of laccase for the synthesis of potential new antibiotics. The biological activity of the new compounds stimulates intensified pharmacological tests.

  通过使用来自曲霉菌或嗜热菌丝体的酶，将 2,5-二羟基苯甲酸衍生物与氨基头孢菌素头孢羟氨苄、头孢氨苄、头孢克洛以及结构相关的卡巴匹林洛拉贝夫进行胺化，合成了 16 种新型头孢菌素。在琼脂扩散试验中，所有产品都能抑制几种革兰氏阳性细菌菌株的生长，其中包括耐甲氧西林金黄色葡萄球菌和耐万古霉素肠球菌。这些产品能保护小鼠免受金黄色葡萄球菌的感染，这种感染对对照组动物来说是致命的。新化合物的细胞毒性和急性毒性几乎可以忽略不计。研究结果表明，漆酶可用于合成潜在的新抗生素。新化合物的生物活性激发了更多的药理学试验。
• Enzymatic cyclizations using laccases: Multiple bond formation between dihydroxybenzoic acid derivatives and aromatic amines
  作者：Veronika Hahn、Timo Davids、Michael Lalk、Frieder Schauer、Annett Mikolasch

  DOI：10.1039/b920081a

  日期：——

  Oxidative C–N bond formation followed by cyclization of dihydroxybenzoic acid derivatives with aromatic and heteroaromatic amines was catalyzed in the presence of oxygen by laccases [E.C. 1.10.3.2] from the white rot fungi Pycnoporus cinnabarinus and Myceliophthora thermophila. The laccase-catalyzed formation of cycloheptenes, cyclooctenes, diazaspiro cyclohexenes, and phenazines was investigated for

  氧化性C–N键形成，随后 环化 的 二羟基苯甲酸 芳族和杂芳族胺的衍生物在下列物质的存在下进行了催化。 氧 通过漆酶[欧共体。1.10.3.2]来自白腐真菌Pycnoporus cinnabarinus和嗜热毁丝霉菌。这漆酶环己烯，环辛烯，二氮杂螺环己烯和吩嗪的催化形成研究是关于环的大小和取代基的首次研究。 芳香胺以及基板的替换图案。没有C-N键形成的差异环化 讨论。
• Synthesis of New N-Analogous Corollosporine Derivatives with Antibacterial Activity by Laccase-Catalyzed Amination
  作者：Annett Mikolasch、Susanne Hessel、Manuela Gesell Salazar、Helfried Neumann、Katrin Manda、Dirk Gōrdes、Enrico Schmidt、Kerstin Thurow、Elke Hammer、Ulrike Lindequist、Matthias Beller、Frieder Schauer

  DOI：10.1248/cpb.56.781

  日期：——

  Corollosporine isolated from the marine fungus Corollospora maritima and N-analogous corollosporines are antimicrobial substances. Owing to the basic structure of the N-analogous corollosporines, they have become an attractive target for laccase-catalyzed derivatisation. In this regard we report on the straightforward laccase-catalyzed amination of dihydroxylated arenes with N-analogous corollosporines. In biological assays the obtained amination products are more active than the parent compounds.

  从海洋真菌 Corollospora maritima 中分离出的珊瑚霉素和 N-类似珊瑚霉素是一种抗菌物质。由于 N-analogous corollosporines 的基本结构，它们已成为漆酶催化衍生化的诱人目标。在这方面，我们报告了漆酶催化二羟基烷与 N-类似冠霉素胺化的简单方法。在生物检测中，所获得的胺化产物比母体化合物更具活性。
• Laccase-catalyzed derivatization of 6-aminopenicillanic, 7-aminocephalosporanic and 7-aminodesacetoxycephalosporanic acid
  作者：Annett Mikolasch、Elke Hammer、Sabine Witt、Ulrike Lindequist

  DOI：10.1186/s13568-020-01117-0

  日期：2020.12

  Trametes spec. laccase (EC 1.10.3.2.) mediates the oxidative coupling of 6-aminopenicillanic, 7-aminocephalosporanic, and 7-aminodesacetoxycephalosporanic acid with 2,5-dihydroxybenzoic acid derivatives to form new penicillin and cephalosporin structures, respectively. The heteromolecular hybrid dimers are formed by nuclear amination of the p-hydroquinones with the primary amines and inhibited in vitro

  Trametes规格 漆酶（EC 1.10.3.2。）介导6-氨基青霉素，7-氨基头孢烷酸和7-氨基去乙酰氧基头孢菌酸与2,5-二羟基苯甲酸衍生物的氧化偶联分别形成新的青霉素和头孢菌素结构。异分子杂合二聚体是通过对氢苯醌与伯胺的核胺化作用形成的，并在体外抑制葡萄球菌菌种的生长，包括一些耐多药菌株。

表征谱图