5-tert-butyl-1,2,4-trihydroxybenzene | 4857-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-tert-butyl-1,2,4-trihydroxybenzene
• 英文别名: 5-tert-butyl-1,2,4-benzenetriol；5-tert-butyl-benzene-1,2,4-triol；5-tert-Butyl-benzen-1,2,4-triol；2-tert-butyl-5-hydroxy-hydroquinone；2,4,5-Trihydroxy-tert.-butyl-benzol；2-Hydroxy-5-tert.-butylhydrochinon；5-Tert-butylbenzene-1,2,4-triol
• CAS: 4857-74-3
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: WYPNQQXXKIHLFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-1,2,4-trihydroxybenzene 在 对苯醌 作用下， 生成 2-Methoxy-5-tert-butyl-benzochinon-(1,4)
  参考文献：
  名称：

  Flaig et al., Justus Liebigs Annalen der Chemie, 1955, vol. 597, p. 196,211

  摘要：

  DOI：
• 作为产物：
  描述：

  4-叔-丁基苯-1,3-二醇 在 copper(II) perchlorate sodium hydroxide 、 偏二甲肼 作用下， 以 氘代二甲亚砜 、 水 、 乙腈 为溶剂， 反应 23.5h， 生成 5-tert-butyl-1,2,4-trihydroxybenzene
  参考文献：
  名称：

  Temporary Inactivation of Plasma Amine Oxidase by Alkylhydrazines. A Combined Enzyme/Model Study Implicates Cofactor Reduction/Reoxidation but Cofactor Deoxygenation and Subsequent Reoxygenation in the Case of Hydrazine Itself

  摘要：

  It has been known for some time that hydrazine and its methyl and 1,1-dimethyl analogues induce inactivation of the copper-containing quinone-dependent plasma amine oxidase but that the activity recovers over time, suggesting metabolism of all three inhibitors. However, the mechanism responsible for loss and regain of activity has not been investigated. In this study a combination of enzyme studies under a controlled atmosphere along with model studies using 5-tert-butyl-2-hydroxy-1,4-benzoquinone to mimic the 2,4,5-trihydroxyphenylalanine quinone (TPQ) cofactor of the enzyme suggest that regain of enzyme activity represents two different Os-dependent processes. In the case of methylhydrazine and 1,1-dimethylhydrazine, we propose that the inactive methyl hydrazone/azo form of the enzyme slowly rehydrates and eliminates MeN=NH to give the triol cofactor form, which instantly reoxidizes to the catalytically active quinone form in the presence of O-2 Metabolism of methylhydrazine represents its conversion to CH4 and N-2, and of 1,1-dimethylhydrazine to CH2=O, CH4, and N-2. In the case of hydrazine itself, however, we propose that the inactive hydrazone/azo form of the enzyme instead undergoes a slow decomposition, probably facilitated by the active-site copper, to give Nz and a novel 5-desoxy resorcinol form of the cofactor. The latter undergoes a rapid, but noninstantaneous reoxygenation at C5 to restore the active cofactor form, also probably mediated by the active-site copper.

  DOI：

  10.1021/jo001115o

文献信息

• 3-Pyrrolines Are Mechanism-Based Inactivators of the Quinone-Dependent Amine Oxidases but Only Substrates of the Flavin-Dependent Amine Oxidases
  作者：Younghee Lee、Ke-Qing Ling、Xingliang Lu、Richard B. Silverman、E. M. Shepard、D. M. Dooley、Lawrence M. Sayre

  DOI：10.1021/ja0205434

  日期：2002.10.1

  previously reported that 3-pyrroline and 3-phenyl-3-pyrroline effect a time-dependent inactivation of the copper-containing quinone-dependent amine oxidase from bovine plasma (BPAO) (Lee et al. J. Am. Chem. Soc. 1996, 118, 7241-7242). Quinone cofactor model studies suggested a mechanism involving stoichiometric turnover to a stable pyrrolylated cofactor. Full details of the model studies are now reported

  我们之前曾报道过，3-吡咯啉和 3-苯基-3-吡咯啉会影响牛血浆中含铜醌依赖性胺氧化酶 (BPAO) 的时间依赖性失活（Lee 等人，J. Am. Chem. Soc. 1996, 118, 7241-7242)。醌辅因子模型研究表明涉及化学计量转换为稳定的吡咯化辅因子的机制。现在报告了模型研究的全部细节以及 3-芳基-3-吡咯啉（芳基 = 取代苯基、1-萘基、2-萘基）家族对 BPAO 抑制的数据，4-甲氧基-3 -硝基苯基类似物是最有效的。同时，母体 3-苯基类似物是来自牛肝的黄素依赖性线粒体单胺氧化酶 B 的纯底物。对被 4-甲氧基-3-硝基苯基类似物灭活的 BPAO 的光谱研究（包括共振拉曼）与 2,4,5-三羟基苯丙氨酸醌 (TPQ) 辅因子的共价衍生一致。作为一个胺氧化酶家族的灭活剂和另一个胺氧化酶家族的纯底物的一类化合物的区别代表了开发哺乳动物含铜胺氧化酶的选择性抑制剂的独特线索。
• Penam derivatives for treating bacterial infections
  申请人：TenNor Therapeutics Limited

  公开号：US11040987B2

  公开（公告）日：2021-06-22

  Novel iron chelating group conjugated penam derivatives described herein show antibacterial activity, and could be used as antibacterial agents or beta-lactamase inhibitors (BLIs) which are of value for application in combination with other antibacterial agents.

  本文所述的新型铁螯合基团共轭五氯化萘衍生物具有抗菌活性，可用作抗菌剂或β-内酰胺酶抑制剂（BLIs），具有与其他抗菌剂联合应用的价值。
• [EN] LIGNIN OXIDATION AND PRODUCTS THEREOF<br/>[FR] OXYDATION DE LA LIGNINE ET PRODUITS DÉRIVÉS
  申请人：STRATEGIC ENZYME APPLIC INC

  公开号：WO2012075053A3

  公开（公告）日：2012-08-02
• Musso,H.; Maassen,D., Justus Liebigs Annalen der Chemie, 1965, vol. 689, p. 93 - 108
  作者：Musso,H.、Maassen,D.

  DOI：——

  日期：——
• Lee Younghee; Sayre, Journal of the American Chemical Society, 1995, vol. 117, # 48, p. 11823 - 11828
  作者：Lee Younghee、Sayre

  DOI：——

  日期：——