8-phenoxycaffeine | 6279-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-phenoxycaffeine
• 英文别名: 1,3,7-trimethyl-8-phenoxy-3,7-dihydro-purine-2,6-dione；1,3,7-Trimethyl-8-phenoxy-3,7-dihydro-purin-2,6-dion；1,3,7-trimethyl-8-phenoxy-3,7-dihydro-1H-purine-2,6-dione；1,3,7-trimethyl-8-phenoxypurine-2,6-dione
• CAS: 6279-37-4
• 化学式: C₁₄H₁₄N₄O₃
• 分子量: 286.29
• InChiKey: NSTBRYLMPPVUSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-phenoxycaffeine 在 magnesium bis(monoperoxyphthalate)hexahydrate 、 溴棕三甲铵 作用下， 以 氯仿 、 水 为溶剂， 反应 40.0h， 以52%的产率得到3-phenoxy-4,7,9-trimethyl-1-oxo-2,4,7,9-tetraazaspiro<4,5>dec-2-ene-6,8,10-trione
  参考文献：
  名称：

  Amer, Adel, Organic Preparations and Procedures International, 1994, vol. 26, # 3, p. 353 - 355

  摘要：

  DOI：
• 作为产物：
  描述：

  咖啡因 在 caesium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 8-phenoxycaffeine
  参考文献：
  名称：

  通过DoE优化（杂）戊烯的电化学CH功能化。

  摘要：

  提出了一种新的方法来激活包括咖啡因和茶碱在内的不同的芳烃和嘌呤。1,1,1,1,3,3,3-六氟异丙醇（HFIP）芳基醚的简单，安全和可扩展的电化学合成是使用带有硼掺杂金刚石（BDD）电极的简易电解装置进行的。获得了高达59％的高产率。三乙胺被用作碱，因为它与HFIP形成高导电性介质，从而使多余的辅助电解质成为多余。使用实验设计（DoE）技术优化了合成，从而深入了解了反应参数的重要性。通过循环伏安法（CV）研究了该机理。随后的过渡金属催化以及无金属官能化导致有趣的图案，产率高达94％。

  DOI：

  10.1002/chem.202001171

文献信息

• 8-Aryl- and alkyloxycaffeine analogues as inhibitors of monoamine oxidase
  作者：Belinda Strydom、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.ejmech.2011.05.014

  日期：2011.8

  Recently it was reported that a series of 8-benzyloxycaffeine analogues are potent reversible inhibitors of human monoamine oxidase (MAO) A and B. In an attempt to discover additional C8 oxy substituents of caffeine that lead to potent MAO inhibition, a series of related 8-aryl- and alkyloxycaffeine analogues were synthesized and their MAO-A and -B inhibition potencies were compared to those of the 8-ben-zyloxycaffeines. The results document that while the 8-substituted-oxycaffeine analogues inhibited both human MAO isoforms, they displayed a high degree of selectivity for MAO-B. 8-(3-Phenylpropoxy) caffeine, 8-(2-phenoxyethoxy)caffeine and 8-[(5-methylhexyl)oxy]caffeine were found to be the especially potent MAO-B inhibitors with IC(50) values ranging from 0.38 to 0.62 mu M. These inhibitors are therefore 2.5-4.6 fold more potent MAO-B inhibitors than is 8-benzyloxycaffeine (IC(50) = 1.77 mu M). It is also demonstrated that, analogous to 8-benzyloxycaffeine, halogen substitution on the phenyl ring of the C8 substituent significantly enhances MAO binding affinity. For example, the most potent MAO-B inhibitor of the present series is 8-[2-(4-bromophenoxy)ethoxy]caffeine with an IC(50) value of 0.166 mu M. This study also reports possible binding orientations of selected oxy caffeines within the active site cavities of MAO-A and MAO-B. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Baumann, vol. 10, p. 134
  作者：Baumann

  DOI：——

  日期：——
• Magnanini, Chemische Berichte, 25 Ref. <1892>, 45
  作者：Magnanini

  DOI：——

  日期：——
• Electrochemical C−H Functionalization of (Hetero)Arenes—Optimized by DoE
  作者：Maurice Dörr、Johannes L. Röckl、Jonas Rein、Dieter Schollmeyer、Siegfried R. Waldvogel

  DOI：10.1002/chem.202001171

  日期：2020.8.12

  presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron‐doped diamond (BDD) electrodes. Good yields up to 59 % were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized

  提出了一种新的方法来激活包括咖啡因和茶碱在内的不同的芳烃和嘌呤。1,1,1,1,3,3,3-六氟异丙醇（HFIP）芳基醚的简单，安全和可扩展的电化学合成是使用带有硼掺杂金刚石（BDD）电极的简易电解装置进行的。获得了高达59％的高产率。三乙胺被用作碱，因为它与HFIP形成高导电性介质，从而使多余的辅助电解质成为多余。使用实验设计（DoE）技术优化了合成，从而深入了解了反应参数的重要性。通过循环伏安法（CV）研究了该机理。随后的过渡金属催化以及无金属官能化导致有趣的图案，产率高达94％。
• Amer, Adel, Organic Preparations and Procedures International, 1994, vol. 26, # 3, p. 353 - 355
  作者：Amer, Adel

  DOI：——

  日期：——