7-(trifluoromethyl)alloxazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 7-(trifluoromethyl)alloxazine
• 英文别名: 7-trifluoromethyl-alloxazine；7-Trifluoromethyl-10H-benzo[g]pteridine-2,4-dione；7-(trifluoromethyl)-1H-benzo[g]pteridine-2,4-dione
• 化学式: C₁₁H₅F₃N₄O₂
• 分子量: 282.182
• InChiKey: GWOCYYKUHWETAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  四氧嘧啶 、 3,4-二胺基苄氧基三氟化物 在 硼酸 、 溶剂黄146 作用下， 反应 3.0h， 生成 8-(trifluoromethyl)alloxazine 、 7-(trifluoromethyl)alloxazine
  参考文献：
  名称：

  N，N，N-1，3，5-三烷基黄素衍生物的制备和氧化还原性质及其作为氧化还原催化剂的活性。

  摘要：

  合成了八种不同的黄素衍生物，并研究了不同位置的取代基对黄素氧化还原化学的电子影响。通过循环伏安法测定的黄素的氧化还原电位与其在甲基对甲苯基硫化物的H2O2氧化中作为催化剂的效率相关。吸电子基团的引入增加了还原的催化剂前体的稳定性。

  DOI：

  10.1002/chem.200400540

文献信息

• Electron-Deficient Alloxazinium Salts: Efficient Organocatalysts of Mild and Chemoselective Sulfoxidations with Hydrogen Peroxide
  作者：Petra Ménová、Hana Dvořáková、Václav Eigner、Jiří Ludvík、Radek Cibulka

  DOI：10.1002/adsc.201300617

  日期：2013.11.25

  AbstractA series of substituted alloxazinium perchlorates has been prepared and tested as catalysts for the oxidation of sulfides to sulfoxides with hydrogen peroxide. The logarithms of the observed rate constants of thioanisole oxidation correlate with the Hammett σ constants of the substituents on the alloxazinium catalysts, as well as with their reduction potentials E0′ and their pKR+ values, representing the alloxazinium salt/pseudobase equilibrium. The stronger the electron‐withdrawing substituent, the more efficient is the alloxazinium catalyst. The alloxazinium salts with a cyano or trifluoromethyl group in position 8 proved to be the most efficient, operating at room temperature at small loadings, down to 0.1 mol%, achieving turnover number values of up to 640 and acceleration by a factor of 350 relative to the non‐catalyzed oxidation. The 8‐cyanoalloxazinium perchlorate was evaluated as the best catalyst; however, due to its relatively good accessibility, the 8‐(trifluoromethyl)alloxazinium perchlorate seems to be the catalyst of choice for sulfoxidations with hydrogen peroxide. It was successfully tested for the sulfoxidation of a series of aliphatic and aromatic sulfides on a preparative scale. It produced the corresponding sulfoxides in quantitative conversions and with high isolated yields (87–98%). No over‐oxidation to sulfone was ever observed.magnified image
• Preparation and Redox Properties of<i>N</i>,<i>N</i>,<i>N</i>-1,3,5-Trialkylated Flavin Derivatives and Their Activity as Redox Catalysts
  作者：Auri A. Lindén、Nina Hermanns、Sascha Ott、Lars Krüger、Jan-E. Bäckvall

  DOI：10.1002/chem.200400540

  日期：2005.1

  Eight different flavin derivatives have been synthesized and the electronic effects of substituents in various positions on the flavin redox chemistry were investigated. The redox potentials of the flavins, determined by cyclic voltammetry, correlated with their efficiency as catalysts in the H2O2 oxidation of methyl p-tolyl sulfide. Introduction of electron-withdrawing groups increased the stability

  合成了八种不同的黄素衍生物，并研究了不同位置的取代基对黄素氧化还原化学的电子影响。通过循环伏安法测定的黄素的氧化还原电位与其在甲基对甲苯基硫化物的H2O2氧化中作为催化剂的效率相关。吸电子基团的引入增加了还原的催化剂前体的稳定性。