1,3-dimethyl-6-(2-oxo-2-phenylethyl)pteridine-2,4(1H,3H)-dione | 647826-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dimethyl-6-(2-oxo-2-phenylethyl)pteridine-2,4(1H,3H)-dione
• 英文别名: 6-benzoylmethyl-1,3-dimethyllumazine；1,3-Dimethyl-6-phenacylpteridine-2,4-dione
• CAS: 647826-49-1
• 化学式: C₁₆H₁₄N₄O₃
• 分子量: 310.312
• InChiKey: RWRARCHLNJNTCS-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  522.9±60.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-chloro-1,3-dimethylpteridine-2,4(1H,3H)-dione 在 tris-(dibenzylideneacetone)dipalladium(0) 哌啶 、 copper(l) iodide 、 bis(pyridine)silver(I) permanganate 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168002.0h， 生成 1,3-dimethyl-6-(2-oxo-2-phenylethyl)pteridine-2,4(1H,3H)-dione
  参考文献：
  名称：

  摘要：

  Sonogashira cross-coupling of 6-chloro-1,3-dimethyllumazine with terminal alkynes gave 6-alkynyl derivatives in good yields. Oxidative amination of the latter with primary alkylamines was accompanied by the pyrrole-ring closure to form 1-R'-2-R-6,8-dimethylpyrrolo[3,2-g]pteridine-5,7(6H,8H)-diones. The addition of bromine to 6-alkynyllumazines afforded the corresponding dibromoalkenes whose treatment with sodium trithiocarbonate gave rise to 2-R-6,8-dimethyltliieno[3,2-g]pteridine-5,7(6H,8H)-diones. The latter compounds are close analogs of the metabolite of molybdenum cofactor (molybdopterine).

  DOI：

  10.1023/a:1024891530684

文献信息

• Pteridines. Part CXVII
  作者：Kiyoshi Torigoe、Naohiro Kariya、Kazuyuki Soranaka、Wolfgang Pfleiderer

  DOI：10.1002/hlca.200790118

  日期：2007.6

  A series of side chain reactions starting from the 6- and 7-styryl-substituted 1,3-dimethyllumazines 1 and 21 as well as from the 6- and 7-[2-(methoxycarbonyl)ethenyl]-substituted 1,3-dimethyllumazine 2 and 22 were performed first by addition of Br2 to the CC bond forming the 1′,2′-dibromo derivatives 3, 4, 24, and 26 in high yields (Schemes 1 and 3) (lumazine=pteridine-2,4(1H,3H)-dione). Treatment

  从6-和7-苯乙烯基取代的1,3- dimethyllumazines开始一系列的侧链反应的1和21，以及从所述6-和7-〔2-（甲氧羰基）乙烯基] -取代1,3- dimethyllumazine 2和22首先通过加入Br中进行2向CC键形成的1'，2'-二溴衍生物3,4，24，和26以高收率（方案1和3）（lumazine =蝶啶-2,4- （1 H，3 H）-二酮）。治疗3带有各种亲核试剂的化合物在7位产生意外的远位取代，并消除了产生7-烷氧基-（参见5和6），7-羟基-（参见7）和7-氨基-6-苯乙烯基的Br原子。-1,3- dimethyllumazines（参见8 - 11）（方案1）。在另一方面，4后行，用稀DBU（1,8-二氮杂双环[5.4.0]十一碳-2-烯），一个正常的HBr消除在侧链中导致18，而用的MeONa处理，得到了更严重的结构性更改为19。同样地，24和26反
• ——
  作者：A. V. Gulevskaya、Dang Van Shee、A. F. Pozharskii

  DOI：10.1023/a:1024891530684

  日期：——

  Sonogashira cross-coupling of 6-chloro-1,3-dimethyllumazine with terminal alkynes gave 6-alkynyl derivatives in good yields. Oxidative amination of the latter with primary alkylamines was accompanied by the pyrrole-ring closure to form 1-R'-2-R-6,8-dimethylpyrrolo[3,2-g]pteridine-5,7(6H,8H)-diones. The addition of bromine to 6-alkynyllumazines afforded the corresponding dibromoalkenes whose treatment with sodium trithiocarbonate gave rise to 2-R-6,8-dimethyltliieno[3,2-g]pteridine-5,7(6H,8H)-diones. The latter compounds are close analogs of the metabolite of molybdenum cofactor (molybdopterine).