8-fluorocaffeine | 42297-34-7

• 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-fluorocaffeine
• 英文别名: 8-fluorocaffein；8-fluoro-1,3,7-trimethylpurine-2,6-dione
• CAS: 42297-34-7
• 化学式: C₈H₉FN₄O₂
• 分子量: 212.183
• InChiKey: CDBGCIJBOBMKCH-UHFFFAOYSA-N

物化性质

• 沸点：
  403.4±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  咖啡因 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 反应 17.0h， 以40.3%的产率得到8-fluorocaffeine
  参考文献：
  名称：

  Functionalization Including Fluorination of Nitrogen-Containing Compounds Using Electrochemical Oxidation.

  摘要：

  含氮化合物在以Et3N-3HF为电解质的条件下进行了电化学氧化。咖啡因的氧化产物为8-氟咖啡因，产率为40.3%。鸟苷四乙酸酯和尿苷三乙酸酯分别给出了17.5%和4.6%的氟化化合物。咖啡因与甲醇、KCl或KCN的类似电化学氧化分别得到了8-甲氧基咖啡因、8-氯咖啡因或8-氰基咖啡因。

  DOI：

  10.1248/cpb.44.1141

文献信息

• Functionalisation including fluorination of caffeine, guanosine tetraacetate, and uridine triacetate using electrochemical oxidation
  作者：Masakazu Sono、Naoko Toyoda、Yoshikazu Shizuri、Motoo Tori

  DOI：10.1016/0040-4039(94)88476-5

  日期：1994.12

  The title compounds have been subjected to electrochemical oxidation with Et3N-3HF as an electrolyte. Caffeine afforded 8-fluorocaffeine as a sole product in 43% yield. Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 7.3 and 4.8 % yield, respectively. Similar electrochemical oxidation of caffeine with methanol, KCl or KCN yielded 8-methoxycaffeine, 8-chlorocaffeine,

  标题化合物已经用Et 3 N-3HF作为电解质进行了电化学氧化。咖啡因提供8-氟咖啡因作为唯一产品​​，收率为43％。鸟嘌呤四乙酸酯和尿苷三乙酸酯分别以7.3％和4.8％的收率得到氟化化合物。用甲醇，KCl或KCN对咖啡因进行类似的电化学氧化，分别制得8-甲氧基咖啡因，8-氯咖啡因或8-氰基咖啡因。
• Skulski, Lech; Wroczynski, Piotr, Polish Journal of Chemistry, 1982, vol. 56, # 7/8/9, p. 975 - 982
  作者：Skulski, Lech、Wroczynski, Piotr

  DOI：——

  日期：——
• In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides
  作者：Phillip J. Milner、Yang Yang、Stephen L. Buchwald

  DOI：10.1021/acs.organomet.5b00631

  日期：2015.10.12

  A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.
• Functionalization Including Fluorination of Nitrogen-Containing Compounds Using Electrochemical Oxidation.
  作者：Masakazu SONO、Naoko TOYODA、Kahori SHIMIZU、Eiji NODA、Yoshikazu SHIZURI、Motoo TORI

  DOI：10.1248/cpb.44.1141

  日期：——

  Nitrogen-containing compounds have been subjected to electrochemical oxidation with Et3N-3HF as an electrolyte. Caffeine afforded 8-fluorocaffeine as a sole product in 40.3% yield. Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 17.5 and 4.6% yields, rspectively. Similar electrochemical oxidation of caffeine with methanol, KCl, or KCN afforded 8-methoxycaffeine, 8-chlorocaffeine, or 8-cyanocaffeine, respectively.

  含氮化合物在以Et3N-3HF为电解质的条件下进行了电化学氧化。咖啡因的氧化产物为8-氟咖啡因，产率为40.3%。鸟苷四乙酸酯和尿苷三乙酸酯分别给出了17.5%和4.6%的氟化化合物。咖啡因与甲醇、KCl或KCN的类似电化学氧化分别得到了8-甲氧基咖啡因、8-氯咖啡因或8-氰基咖啡因。