2,3,5,6-tetrafluoro-4-(hydroxymethyl)phenol | 61596-38-1

• 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: 2,3,5,6-tetrafluoro-4-(hydroxymethyl)phenol
• CAS: 61596-38-1
• 化学式: C₇H₄F₄O₂
• 分子量: 196.101
• InChiKey: OERWOOHCPAZTKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetrafluoro-4-(hydroxymethyl)phenol 在 indium 、 氯化亚砜 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 aceto-β-glucuronic acid methyl ester 2,3,5,6-tetrafluoro-para-hydroxybenzyl β-lapa-ketol
  参考文献：
  名称：

  [EN] QUINONE PROTECTED FORMS AND CONJUGATES
  [FR] FORMES PROTÉGÉES DE QUINONE ET CONJUGUÉS

  摘要：

  The invention provides protected ortho-quinone compounds comprising a group represented by: Formula (I) where -Ar- is optionally substituted phenylene, -X is selected from -NH2, -OH and -SH, and the protected forms of each, -W- is optionally substituted methylene, such as methylene, and d is a double or single bond, and the salts and solvates thereof

  公开号：

  WO2023227757A1
• 作为产物：
  描述：

  2,3,5,6-四氟-4-羟基苯甲醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以65%的产率得到2,3,5,6-tetrafluoro-4-(hydroxymethyl)phenol
  参考文献：
  名称：

  Mechanism and Mechanism-Based Inactivation of 4-Hydroxyphenylpyruvate Dioxygenase

  摘要：

  Six substrate analogs of 4-hydroxyphenylpyruvate, specifically pentafluorophenylpyruvate, 4-hydroxytetrafluorophenylpyruvate,2-thienylpyruvate, 3-thienylpyruvate, thiophenol oxalate, and p-thiocresoloxalate were synthesized and their interactions with porcine liver 4-hydroxyphenylpyruvate dioxygenase investigated. Both pentafluorophenylpyruvate and thiophenol oxalate are competitive inhibitors of the enzyme with Ki values of 14 and 150 mu M, respectively, but p-thiocresol oxalate has no effect on the enzymic activity. The other three substrate analogs are both substrates and mechanism-based inactivators of the enzyme with the following kinetic characteristics (compound, K-m, V-max, k(mact), K', partition ratio) at pH 6.0, 37 degrees C, and an air atmosphere: 4-hydroxytetrafluorophenylpyruvate, 50 mu M, 1.9 mkat/ kg, 1.5/min, 70 mu M 4.2; 2-thienylpyruvate, 500 mu M, 7.8 mkat/kg, 0.6/min, 400 CLM, 41; 3thienylpymvate, 250 mu M, 2 9 mkatikg, 0.6/min, 300 CLM, 22. When inactivated, the dioxygenase was found to contain per mole of active enzyme, 0.78 mol of label from 3-thienyt3 [3H]pyruvate and 0.85 mol of label from 4-hydroxytetrafluorophenyl-3 [3H]pyruvate. The product formed from the enzyme-catalyzed oxidation of 3-thienylpyruvate was determined to be 3-carboxymethyl-3-thiolene-2-one. The implication of these results to the mechanism of the dioxygenase is considered, (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1028

文献信息

• Rational Design, Synthesis and Biological Evaluation of Modular Fluorogenic Substrates with High Affinity and Selectivity for PTP1B
  作者：Silvano Sanchini、Francesca Perruccio、Grazia Piizzi

  DOI：10.1002/cbic.201400033

  日期：2014.5.5

  released through an enzyme‐initiated 1,6‐elimination reaction. Optimisation of the stereoelectronic properties and of the binding interactions at the enzyme active site led to substrates with high affinity and promising selectivity.

  智能探针：氨基香豆素潜在的发色团通过酶引发的1,6消除反应释放。立体电子性质和在酶活性位点的结合相互作用的优化导致底物具有高亲和力和有希望的选择性。
• Activity-based probe compounds, compositions, and methods of use
  申请人：THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY

  公开号：US10829477B2

  公开（公告）日：2020-11-10

  Activity-based probe compounds for use in labeling a cysteine protease are provided. The compounds are targeted to the protease through a specific targeting element. The compounds additionally include a detectable element, such as a fluorescent label, a radiolabel, or a chelator. In some cases, the compounds additionally include a quenching element that is released upon reaction with the protease. Also provided are compositions comprising the compounds and methods for using the compounds, for example in labeling a protease in an animal and in visualizing a tumor in an animal.

  提供了用于标记半胱氨酸蛋白酶的基于活性的探针化合物。这些化合物通过特定的靶向元件靶向蛋白酶。化合物还包括可检测元素，如荧光标签、放射性标签或螯合剂。在某些情况下，化合物还包括一种淬灭元素，在与蛋白酶反应时释放出来。此外，还提供了包含这些化合物的组合物和使用这些化合物的方法，例如标记动物体内的蛋白酶和观察动物体内的肿瘤。
• Brooke, Gerald M.; Ferguson, J. A. K. Jamie, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2091 - 2098
  作者：Brooke, Gerald M.、Ferguson, J. A. K. Jamie

  DOI：——

  日期：——
• Budnik,A.G. et al., Journal of Organic Chemistry USSR (English Translation), 1978, vol. 14, p. 1185 - 1189
  作者：Budnik,A.G. et al.

  DOI：——

  日期：——
• BROOKE, GERALD M.;FERGUSON, J. A. K. JAMIE, J. CHEM. SOC. PERKIN TRANS.,(1987) N 9, 2091-2097
  作者：BROOKE, GERALD M.、FERGUSON, J. A. K. JAMIE

  DOI：——

  日期：——