6-chloro-5-formyl-3-phenyluracil | 35824-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-chloro-5-formyl-3-phenyluracil
• 英文别名: 3-Phenyl-5-formyl-6-chlorouracil；6-chloro-2,4-dioxo-3-phenyl-1H-pyrimidine-5-carbaldehyde
• CAS: 35824-99-8
• 化学式: C₁₁H₇ClN₂O₃
• 分子量: 250.641
• InChiKey: CVGPIUZDQVRIEI-UHFFFAOYSA-N

物化性质

• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-5-formyl-3-phenyluracil 在 trithylamine 、 三氯氧磷 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 10.5h， 生成 4-oxo-3,7-diphenyl-9-(3-ethyl-2(3H)-benzothiazolylidine)methyl-3,4-dihydrothiazolo<3,4-a>pyrimido<5,4-e>pyrimidinium-2-oxide
  参考文献：
  名称：

  Condensed heterocycles with a thiazole nucleus. 8. Thiazolo[4,3-a]pyrimido[5,4-e]pyrimidines

  摘要：

  DOI：

  10.1007/bf00513584

文献信息

• Autorecycling system for reduction of carbonyl compounds to alcohols by 1,5-dihydro-5-deazaflavins
  作者：Fumio Yoneda、Kazunori Kuroda、Mutsuko Kamishimoto

  DOI：10.1039/c39810001160

  日期：——

  An effective recycling system for the reduction of carbonyl compounds to alcohols was constructed for the first time using 5-deazaflavins and formic acid, in such a way that each mol of the compound catalyses the reduction, by formic acid, of up to 25 mol of benzaldehyde.

  首次构建了一种有效的回收系统，用于将羰基化合物还原为醇，使用了5-脱氮氟黄素和甲酸，以一种方式使每摩尔化合物催化甲酸对多达25摩尔苯甲醛的还原。
• The autorecycling oxidation of benzylamine by synthetic 8-hydroxy-5-deazaflavin derivatives
  作者：Ryoichi Hirayama、Masahiro Kawase、Tetsutaro Kimachi、Kiyoshi Tanaka、Fumio Yoneda

  DOI：10.1002/jhet.5570260509

  日期：1989.9

  Various 8-hydroxy-5-deazaflavin derivatives were synthesized as the model compounds of coenzyme F420-These compounds oxidized benzylamine to benzaldehyde more efficiently than the corresponding 8-unsubstituted 5-deazaflavins.

  合成了多种8-羟基-5-脱氮黄素衍生物作为辅酶F 420的模型化合物。这些化合物比相应的8-未取代的5-脱氮黄素更有效地将苄胺氧化为苯甲醛。
• SYNTHESIS OF 2<i>H</i>-PYRIDO[l′,2′:1,6]PYRIDO[2,3-<i>d</i>]PYRIMIDINE-2,4(3<i>H</i>)DIONES (“BENT 5-DEAZAFLAVINS”) AND THEIR USE IN OXIDATION OF ALCOHOL AND AMINE
  作者：Fumio Yoneda、Masami Ono、Keiko Kira、Hisako Tanaka、Yoshiharu Sakuma、Akira Koshiro

  DOI：10.1246/cl.1980.817

  日期：1980.7.5

  Treatment of 6-chloro-5-formyluracils with 2-benzylpyridines in dimethylformamide gave the corresponding 2H-pyrido[1′,2′:1,6]pyrido[2,3-d.]pyrimidine-2 ,4(3H)diones which are a bent type of 5-deazaflavin. Similarly, treatment of 6-chloro-5-formyl-3-methyluracil with 2-aminopyridine gave a 6-azalog of the above bent 5-deazaflavin, 2H-pyrido-[2′,1′:2,3]pyrimido[4,5-d]pyrimidine-2,4(3H)dione. These “bent 5-deazaflavins” showed oxidizing ability toward benzyl alcohol, cyclohexanol and benzylamine giving the corresponding carbonyl compounds.

  将6-氯-5-甲醛尿嘧啶与2-苄基吡啶在二甲基甲酰胺中反应，得到了相应的2H-吡啶[1′,2′:1,6]吡啶[2,3-d.]嘧啶-2,4(3H)二酮，这是一种弯曲类型的5-脱氨黄素。类似地，将6-氯-5-甲醛-3-甲基尿嘧啶与2-氨基吡啶反应，得到了上述弯曲型5-脱氨黄素的6-氮杂衍生物，2H-吡啶-[2′,1′:2,3]嘧噻咪[4,5-d]嘧啶-2,4(3H)二酮。这些“弯曲的5-脱氨黄素”对苄醇、环己醇和苄胺具有氧化能力，生成相应的羰基化合物。
• Syntheses of 2-deoxo-2-phenyl-5-deazaflavins and 3-phenyl-5-deazaflavins and their use in the oxidation of benzyl alcohol and benzylamine.
  作者：FUMIO YONEDA、KENYA MORI、MASAMI ONO、YOKO KADOKAWA、ETSUKO NAGAO、HIROYUKI YAMAGUCHI

  DOI：10.1248/cpb.28.3514

  日期：——

  Treatment of 6-(N-alkylanilino)-2-phenylpyrimidin-4 (3H)-ones, which were prepared by the condensation of 6-chloro-2-phenylpyrimidin-4 (3H)-one with N-alkylanilines, with the Vilsmeier reagent (dimethylformamide-phosphoryl chloride) gave the corresponding 10-alkyl-2-deoxo-2-phenyl-5-deazaflavins (III) in excellent yields. Heating of 6-chloro-5-formyl-3-phenyluracil with N-alkylanilines in dimethylformamide gave the corresponding 10-alkyl-3-phenyl-5-deazaflavins (VI) in a single step. The abilities of the 5-deazaflavins (III) and (VI) thus obtained to oxidize benzyl alcohol and benzylamine were compared, and some automatic recycling of the oxidation reactions was observed. The reaction of compounds III with benzylamine exceptionally gave the adducts, 5-benzylamino-2-deoxo-2-phenyl-5-deazaflavins.

  将 6-氯-2-苯基嘧啶-4 (3H)-酮与 N-烷基苯胺缩合制备的 6-(N-烷基苯胺)-2-苯基嘧啶-4 (3H)-酮用维尔斯梅尔试剂（二甲基甲酰胺-磷酰氯）处理，可以得到相应的 10-烷基-2-脱氧-2-苯基-5-脱氮黄素（III），产量极高。将 6-氯-5-甲酰基-3-苯基脲嘧啶与 N-烷基苯胺在二甲基甲酰胺中加热，只需一步就能得到相应的 10-烷基-3-苯基-5-去氮黄素（VI）。比较了由此得到的 5-脱氮黄素（III）和（VI）氧化苄醇和苄胺的能力，并观察到氧化反应的一些自动循环。化合物 III 与苄胺的反应特别生成了加合物 5-苄氨基-2-脱氧-2-苯基-5-脱氮黄素。
• 1,3,9,1l,12,14-Hexazapentacene-2,4,8,10(1H,3H,9H,11H)-tetraones (double-headed 5-deazaflavins) with potential for oxido-reduction
  作者：Fumio Yoneda、Kazunori Kuroda、Masakazu Koga、Toshiro Ibuka

  DOI：10.1039/c39840000872

  日期：——

  Condensation of 8-(substituted-amino)-1,5-dihydro-5-deazaflavins with 6-chloro-5-formyuracils, followed by dehydrogenation with diethyl azodicarboxylate gives the corresponding 1,3,9,1l,12,14-hexazapentacene-2,4,8,10(1H,3H,9H,11H)-tetraones, which exhibit strong oxido-reductive abilities.

  将8-（取代的氨基）-1,5-二氢-5-脱氮黄素与6-氯-5-甲酰嘧啶缩合，然后与偶氮二羧酸二乙酯脱氢，得到相应的1,3,9,1l，12,14-六氮杂戊烯-2,4,8,10（1 H，3 H，9 H，11 H）-四酮，具有很强的氧化还原能力。