3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid hydrazide | 2325-01-1

• 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: 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid hydrazide
• 英文别名: 3,5-di-tert-butyl-4-hydroxybenzoyl hydrazide；3,5-di-tert-butyl-4-hydroxybenzohydrazide；3,5-di-t-butyl-4-hydroxybenzhydrazide；4-Hydroxy-3.5-di-tert.-butyl-benzhydrazid；3,5-ditert-butyl-4-hydroxybenzohydrazide
• CAS: 2325-01-1
• 化学式: C₁₅H₂₄N₂O₂
• mdl: MFCD01821356
• 分子量: 264.368
• InChiKey: ZNWRUFKGBSZSDC-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C
• 密度：
  1.062±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid hydrazide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2,4-dihydro-4-methyl-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazoles, -1,3,4-oxadiazoles, and -1,2,4-triazoles as orally active, nonulcerogenic antiinflammatory agents

  摘要：

  To discover dual inhibitors of 5-lipoxygenase (LO) and cyclooxygenase (CO) with improved pharmacokinetic properties, we have designed and synthesized series of 1,2,4-triazole, 1,3,4-oxadiazole, and 1,3,4-thiadiazole di-tert-butylphenol derivatives which exhibit a wide range of log P (2.3 to >4) and pK(a) (5.5-12) values. From this work 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione, choline salt (12a, CI-986) was found to be a potent inhibitor of 5-LO (IC50 = 2.8 muM) and CO (IC50= 0.8 muM), orally active in rat models of inflammation and nonulcerogenic.

  DOI：

  10.1021/jm00060a017
• 作为产物：
  描述：

  4-Hydroxy-3.5-di-tert.-butyl-thiolbenzoesaeure-methylester 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid hydrazide
  参考文献：
  名称：

  Gompper,R. et al., Justus Liebigs Annalen der Chemie, 1965, vol. 684, p. 37 - 57

  摘要：

  DOI：

文献信息

• Stereoselective, solvent free, highly efficient synthesis of aldo- and keto-N-acylhydrazones applying grindstone chemistry
  作者：José Maurício dos Santos Filho、Savio Moita Pinheiro

  DOI：10.1039/c7gc00730b

  日期：——

  A mild and efficient synthesis of N-acylhydrazones has been developed, applying a simple grindstone procedure, leading to a library of 51 examples exhibiting a broad variety of structural features, 21 of them described for the first time in this paper. This methodology works without any organic solvent under the catalysis of acetic acid at room temperature, promotes the formation of essentially pure

  已经开发出了温和而有效的N-酰基hydr酮合成方法，该方法采用了简单的磨石程序，从而产生了51个实例，这些实例均显示出多种结构特征，其中21个实例首次在本文中进行了描述。该方法在室温下在乙酸催化下无需任何有机溶剂即可工作，可促进形成基本纯净的粗产物，并避免繁琐的后处理和有害溶剂的使用以及能耗。另外，如NMR分析所支持的，其导致N-酰基hydr的立体选择性形成。
• Derivatives of N-HALS-substituted amic acid hydrazides
  申请人：Elf Atochem North America, Inc.

  公开号：US05338853A1

  公开（公告）日：1994-08-16

  N-(2,2,6,6-tetraalkyl-4-piperidinyl)amic acid hydrazides contain a light stabilizing group, a heat stabilizing group and an amic acid hydrazide functionality in the same molecule. The amic acid hydrazide functionality in the compounds enhances the photooxidative stabilizing properties of the hindered amine groups and contributes thermal and oxidative stabilizing and metal complexing properties to the compounds. The novel compounds are excellent light stabilizers for polyolefins, have low volatility and are not readily lost from polymeric systems via volatilization, migration or extraction.

  N-(2,2,6,6-四烷基-4-哌啶基)酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸酰肼酸
• Synthesis and ESR study of Co and Ni hydrazides and hydroxamates containing 2,6-di-tert-butylphenol moiety in the ligands
  作者：I. A. Zav'yalov、O. V. Polyakova、E. R. Milaeva、A. I. Prokof'ev

  DOI：10.1007/bf01151299

  日期：1995.9

  hydroxamates containing the 2,6-di-tert-butylphenol moiety as a potential free radical precursor in the ligand environment of the complexes were synthesized. ESR spectroscopy was used to study the dependence of the stability of metal complexes incorporating a paramagnetic center in the ligand on the type of the coordination environment of the metal and the nature of the ligand. The complexes, in which

  合成了一系列含有 2,6-二叔丁基苯酚部分作为复合物配体环境中潜在自由基前体的 Co 和 Ni 酰肼和异羟肟酸酯。ESR 光谱用于研究在配体中包含顺磁中心的金属配合物的稳定性对金属配位环境类型和配体性质的依赖性。其中饱和脂肪族桥接基团将 2,6-二叔丁基苯酚部分与金属的配位环境分开的配合物可以进行氧化以产生稳定的顺磁性物质，在配体环境中具有未配对的电子。配体中自由基中心与金属配位环境的相互作用实际上不存在（除了弱自旋相互作用）。
• Synthesis and study of new phenolic antioxidants with nitroaromatic and heterocyclic substituents
  作者：O. V. Mikhalev、D. B. Shpakovsky、Yu. A. Gracheva、T. A. Antonenko、D. V. Albov、L. A. Aslanov、E. R. Milaeva

  DOI：10.1007/s11172-018-2127-2

  日期：2018.4

  New polyfunctional aromatic, nitroaromatic, and heterocyclic compounds linked to the 2,6-di-tert-butylphenol moiety via –NH–, –C(O)NH–, –S–, or–C=N– spacers were synthesized. These structures provide intramolecular charge transfer (ICT) and exhibit antioxidant activity. The structures of the new compounds were established by X-ray diffraction. The novel compounds were evaluated for antioxidant activity

  合成了通过–NH–、–C(O)NH–、–S– 或–C=N– 间隔基与2,6-二叔丁基苯酚部分连接的新型多功能芳族、硝基芳族和杂环化合物。这些结构提供分子内电荷转移 (ICT) 并表现出抗氧化活性。通过X射线衍射确定了新化合物的结构。使用 DPPH 测定法评估新化合物的抗氧化活性。2,4,6-三硝基苯基部分与–NH–间隔基的结合导致2,6-二叔丁基苯酚的抗氧化活性显着增加。这些化合物也是弱脂氧合酶抑制剂。这项研究的结果为利用 ICT 寻找新型抗氧化剂提供了机会。
• 3,5-di-tertiary-butyl-4-hydroxyphenyl-1,3,4-thiadiazoles, and
  申请人：Warner-Lambert Company

  公开号：US05155122A1

  公开（公告）日：1992-10-13

  The present invention is novel compounds which are 3,5-di-tertiary-butyl-4-hydroxyphenyl substituted 1,2,4- and 1,3,4-thiadazoles and oxadiazoles, and 1,2,4-triazoles, and pharmaceutically acceptable additions and base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like.

  本发明涉及新型化合物，其为3,5-二叔丁基-4-羟基苯基取代的1,2,4-和1,3,4-噻二唑和噁二唑以及1,2,4-三唑，以及其药学上可接受的加合物和碱盐、制药组合物和使用方法。现发现该发明化合物具有作为5-脂氧合酶和/或环氧合酶抑制剂的活性，从而提供治疗因此类抑制而受益的疾病的方法，包括炎症、关节炎、疼痛、发热等。