1,6,7-trimethyl-2,4-dioxo-(1H,3H)pteridine | 50256-21-8

• 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: 1,6,7-trimethyl-2,4-dioxo-(1H,3H)pteridine
• 英文别名: 1,6,7-trimethylpteridine-2,4,(1H,3H)-dione；1,6,7-trimethylmethyllumazine；1,6,7-trimethyllumazine；1,6,7-methyllumazine；1,6,7-trimethyl-1H-pteridine-2,4-dione；1,6,7-Trimethyl-1H-pteridin-2,4-dion；1,6,7-Trimethylpteridine-2,4-dione
• CAS: 50256-21-8
• 化学式: C₉H₁₀N₄O₂
• 分子量: 206.204
• InChiKey: XCOSZAUDQCILGD-UHFFFAOYSA-N

物化性质

• 熔点：
  327-329 °C
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 1,6,7-trimethyl-2,4-dioxo-(1H,3H)pteridine 以 not given 为溶剂， 以70%的产率得到(1,6,7-trimethyllumazine)Re(CO)3Cl
  参考文献：
  名称：

  Rhenium(I) coordinated lumazine and pterin derivatives: structure and spectroelectrochemistry of reversibly reducible (6-ATML)Re(CO)3Cl (6-ATML=6-acetyl-1,3,7-trimethyllumazine)

  摘要：

  A number of complexes between substituted lumazines (2,4-dioxo-(1H,3H)pteridines) or pterins (2-amino-4-oxo-(3H)pteridines) and Re(CO)(3)Cl have been synthesized and characterized electrochemically and spectroscopically. The structure of the (6-ATML)Re(CO)(3)Cl derivative (6-ATML = 6-acetyl-1,3,7-trimethyllumazine) could be determined in [fac-(6-ATML)Re(CO)(3)Cl]. 3C(6)H(6). The rhenium(I) center coordinates in a rather symmetrical fashion through the O4-N5 alpha -carbonylimino chelate site of 6-ATML; the potentially available acetyl function is not involved in the metal coordination. The acetyl acceptor substituent facilitates the reversible one-electron reduction of this compound to a persistent anion radical complex [(6-ATML)Re(CO)(3)Cl](.-), which is accompanied by variable low-frequency shifts of the six carbonyl stretching bands and by the appearance of a broad EPR signal. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(01)00646-6
• 作为产物：
  描述：

  1,3,7-Trimethylpterin 在 sodium hydroxide 作用下， 生成 1,6,7-trimethyl-2,4-dioxo-(1H,3H)pteridine
  参考文献：
  名称：

  Pteridine Chemistry. III. 2-Amino-1(and 3)6,7-trimethyl-4-pteridones and Some Related Compounds

  摘要：

  DOI：

  10.1021/ja01555a050

文献信息

• Isolation, Structural Elucidation, and Synthesis of Lepteridine From Ma̅nuka (<i>Leptospermum scoparium</i>) Honey
  作者：Benjamin J. Daniels、Gordana Prijic、Sarah Meidinger、Kerry M. Loomes、Jonathan M. Stephens、Ralf C. Schlothauer、Daniel P. Furkert、Margaret A. Brimble

  DOI：10.1021/acs.jafc.6b01596

  日期：2016.6.22

  manuka honey. This work reports the identification of a compound previously unreported in manuka honey by HPLC, and determination of the structure of the as 3,6,7 trimethyllumazine using NMR, MS, IR and UV/Vis spectroscopy. This assignment was confirmed by total synthesis. The natural product, renamed lepteridine, was only observed in manuka honeys and could potentially serve as a biomarker for genuine

  麦卢卡蜂蜜是由Leptospermum scoparium的花蜜制成，由于其非过氧化物抗菌活性而赢得了科学和经济利益。由于存在伪造的麦卢卡蜂蜜，对真正麦卢卡蜂蜜的生物标记物的需求日益增加。这项工作报告了通过HPLC鉴定麦卢卡蜂蜜中以前未报道的化合物，并使用NMR，MS，IR和UV / Vis光谱法确定了3,6,7三甲基鲁嗪的结构。通过完全综合证实了该分配。仅在麦卢卡蜂蜜中观察到了天然产物，重命名为lepteridine，可以用作真正的麦卢卡蜂蜜的生物标记。
• Sachs; Meyerheim, Chemische Berichte, 1908, vol. 41, p. 3964
  作者：Sachs、Meyerheim

  DOI：——

  日期：——
• Synthesis and characterization of new complexes formed between 1-methyllumazine and 1,6,7-trimethyllumazine ligand with transition metal(II) nitrate. Crystal structure of cobalt(II), copper(II) and cadmium(II) complexes
  作者：Esther R Acuña-Cueva、Rene Faure、Nuria A Illán-Cabeza、Sonia B Jiménez-Pulido、Miguel N Moreno-Carretero、Miguel Quirós-Olozábal

  DOI：10.1016/s0020-1693(02)01165-9

  日期：2003.1

  The structures and spectroscopic properties of Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) nitrate complexes of 1-methyllumazine (MLM) and 1,6,7-trimethyllumazine (MLMD) with general formula M(II)(NO3)(2)L-2.nH(2)O are reported. In all the complexes, the lumazine-derived ligands seem to be coordinated in bidentate form through the N5 and 04 atoms. The crystal structures of [Cu(MLM)(2)(H2O)(2)](NO3)(2) (1), [Co(MLMD)(2)(H2O)(2)](NO3)(2) (2) and [Cd(MLMD)(2)(NO3)(2)] (3) have been determined by X-ray crystallographic methods. In compounds I and 2 the nitrate anions are uncoordinated, and the metal ions are surrounded in an octahedral geometry by two bidentate lumazine ligands and two coordinated water molecules. The absolute configuration of the complex I can be described as the 4M stereoisomer, following Bailar's nomenclature, with the two lumazine in a cis arrangement and the complex 2 exhibits the 2L stereoisomer as is usually in this kind of complexes. Compound 3 consists of neutral mononuclear units, the Cd(II) environment being a bicapped octahedral close to the trigonal antiprism due to the two nitrate anions coordinating in a very unsymmetrical bidentate mode. (C) 2002 Elsevier Science B.V. All rights reserved.
• Spectral and XRD studies on perchlorate salts of several Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) complexes from 1-methyllumazine and 1,6,7-trimethyllumazine
  作者：Esther R. Acuña-Cueva、René Faure、Nuria A. Illán-Cabeza、Sonia B. Jiménez-Pulido、Miguel N. Moreno-Carretero

  DOI：10.1016/s0277-5387(02)01085-9

  日期：2002.8

  A number of complexes with general formula ML2(ClO4)(2)(.)nH(2)O(.)mCH(3)CN [M -Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II)] have been synthesized by reaction of 1-methyllumazine (MLM) and 1,6,7-trimethyllumazine (MLMD) and perchlorate salts in acetonitrile. The complexes have been characterized by elemental analysis, TG and DSC, as well as by IR, UV-Vis, EPR spectroscopies and magnetic measurements. The crystal structures of [Cu(MLM)(2)(H2O)(2)](CLO4)(2), [Zn(MLM)(2)(H2O)(2)](ClO4)(2) and [Cu(MLM)(MLMD)(H2O)(CH3CN)](ClO4)(2) have been determined by X-ray diffraction methods. In the complexes Cu/MLM and Zn/MLM, the metal ions involve an octahedral geometry with two water molecules and two lumazine ligands coordinated through O4 and N5 atoms. The compound Cu/MLM/MLMD consists of monomeric units in which the CU(II) atom is linked by two different lumazine derivatives (MLM and MLMD), a water and an acetonitrile molecules bonding directly to the metal ion. The environment around metal ion exhibits a geometry between a square-based pyramidal and an elongated tetragonal octahedral due to the different distances Cu-O4 in the apical positions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and characterization of several lumazine derivative complexes of Co(II), Ni(II), Cu(II), Cd(II), Pd(II) and Pt(II). X-ray structures of a mononuclear copper complex and a dinuclear cadmium complex
  作者：Esther R. Acuña-Cueva、René Faure、Nuria A. Illán-Cabeza、Sonia B. Jiménez-Pulido、Miguel N. Moreno-Carretero、Miguel Quirós-Olozábal

  DOI：10.1016/s0020-1693(03)00172-5

  日期：2003.7

  The synthesis of the new Co(II), Ni(II), Cu(II), Cd(II), Pd(II) and Pt(II) complexes with 1-methyllumazine (1-methylpteridine-2,4(1H, 3H)-dione, MLM) and 1,6,7-trymethyllumazine (1,6,7-trimethylpteridine-2,4(1H,3H)-dione, MLMD) is described. The coordination chemistry of these ligands have been investigated and an usual bidentate bonding mode through the N5 and 04 atoms is observed. These complexes present the form (MCl2L)-Cl-II and were characterized by elemental analyses, TG and DSC, as well as by IR, UV-Vis, EPR spectroscopy and magnetic measurements. The crystal structures of [CuCl2(MLM)(H2O)] and [CdCl2(MLM)(H2O)](2) have been determined by X-ray diffraction methods. The copper(II) compound exists in the monomeric form with an environment around the metal ion as a distorted square-based pyramidal geometry whereas the cadmium complex was observed as dimers with an edge-sharing distorted octahedral coordination sphere around each cadmium center. (C) 2003 Elsevier Science B.V. All rights reserved.