6-acetyl-1,3,7-trimethyllumazine | 94591-19-2

• 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: 6-acetyl-1,3,7-trimethyllumazine
• 英文别名: 6-Acetyl-1,3,7-trimethylpteridine-2,4-dione
• CAS: 94591-19-2
• 化学式: C₁₁H₁₂N₄O₃
• 分子量: 248.241
• InChiKey: QIICXDUQNHXBDB-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  457.8±55.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-acetyl-1,3,7-trimethyllumazine 在 硝酸 作用下， 反应 18.0h， 以79%的产率得到1,3,7-trimethyllumazine-6-carboxylic acid
  参考文献：
  名称：

  Selective Oxidation of 6-Acetyl-1,3,7-trimethyllumazine by Nitric Acid

  摘要：

  DOI：

  10.3987/com-98-8460
• 作为产物：
  描述：

  1,3-二甲基-6-亚氨基-5-异亚硝基尿嘧啶 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 6-acetyl-1,3,7-trimethyllumazine
  参考文献：
  名称：

  Giori, P.; Poli, T.; Veronese, A.C., Journal of Heterocyclic Chemistry, 1986, vol. 23, # 6, p. 1661 - 1666

  摘要：

  DOI：

文献信息

• Reductive amination of 6-acetylpteridine to 6-<i>N</i>-arylaminoethylpteridine
  作者：Yasuhiro Kuroda、Kazuhiro Isarai、Shizuaki Murata

  DOI：10.1515/hc-2012-0046

  日期：2012.8.1

  converted to 6-[1-(arylamino)ethyl]pteridine derivatives 8 and 7, respectively, in good to moderate yields by stepwise reactions with p-substituted anilines via imine intermediates using a Lewis acid catalyst followed by treatment with sodium tetrahydroborate. The one-step reductive amination of the starting acetylpteridine also proceeded in the presence of 2-picoline-borane complex in satisfactory yield

  摘要 6-乙酰基-7-甲基蝶啶衍生物 2 和 3（lumazine 和蝶呤）分别转化为 6-[1-(芳氨基)乙基]蝶啶衍生物 8 和 7，通过与对位取代的逐步反应，产率良好至中等。使用路易斯酸催化剂通过亚胺中间体生成苯胺，然后用四氢硼酸钠处理。起始乙酰蝶啶的一步还原胺化也在 2-甲基吡啶-硼烷络合物的存在下以令人满意的产率进行。
• A new five-coordinated CuIP2NO2 system: XRD structure of 6-acetyl-1,3,7-trimethyl-pteridine-2,4(1H,3H)-dione and its Cu(i) (N5,O61,O4)-tridentate complex with triphenylphosphine. An AIM study of the nature of metal–ligand bonds
  作者：Francisco Hueso-Ureña、Sonia B. Jiménez-Pulido、Maria P. Fernández-Liencres、Manuel Fernández-Gómez、Miguel N. Moreno-Carretero

  DOI：10.1039/b807634k

  日期：——

  The second example of a five-coordinated CuIP2NO2 system, [Cu(DLMAceM)(PPh3)2]ClO4 (DLMAceM = 6-acetyl-1,3,7-trimethyl-pteridine-2,4(1H,3H)-dione), is reported. The structural characterization of both the DLMAceM ligand and the Cu(I) compound has been achieved by IR, 13C and 1H NMR and XRD methods. The metal is coordinated to the PPh3 molecules (Cu–P 2.224(2) and 2.258(2) Å) and the pyrazine N(5) atom (Cu–N(5) 2.058(6) Å) in a trigonal planar arrangement; two additional semi-coordinated atoms (Cu⋯O(4) 2.479(5) and Cu⋯O(61) 2.559(5) Å) can be observed, forming an intermediate SP/TBP polyhedron. To define the nature of the metal–ligand bonds for the Cu(I) compound, especially in regards to the semi-coordinated oxygen atoms, a topological analysis of the electron density ρb within the framework provided by the quantum theory of atoms in a molecule (QTAIM) using Hartree–Fock and DFT(B3LYP) levels of theory has been performed. Five bond critical points (BCP) have been found, whose associated bond paths connect the Cu metal with the atoms P(1), P(2), O(4) O(61) and N(5). The type of interaction between the Cu and ligand binding sites has been characterized in terms of the Laplacian of the electron density, ∇2ρb, the total energy density, Hb, and the delocalization index, δAB.

  报告了第二个五配位CuIP2NO2体系，即[Cu(DLMAceM)(PPh3)2]ClO4（DLMAceM = 6-乙酰基-1,3,7-三甲基-蝶啶-2,4(1H,3H)-二酮）。通过红外光谱、13C和1H核磁共振以及X射线衍射方法，对DLMAceM配体和Cu(I)化合物的结构特征进行了表征。金属与PPh3分子（Cu-P 2.224(2)和2.258(2) Å）和吡嗪N(5)原子（Cu-N(5) 2.058(6) Å）以三角平面排列方式配位；可以观察到另外两个半配位原子（Cu¯O(4) 2.479(5)和Cu¯O(61) 2.559(5) Å），形成中间SP/TBP多面体。为了确定Cu(I)化合物的金属-配体键的性质，特别是半配位氧原子的性质，使用Hartree-Fock和DFT(B3LYP)理论水平，对分子中原子量子理论（QTAIM）提供的框架内的电子密度Λb进行了拓扑
• Interactions between 2,4-bis-pteridine-1,5-benzodiazepine and group 12 dihalides: synthesis, spectral and XRD structural studies and theoretical calculations
  作者：Nuria A. Illán-Cabeza、Sonia B. Jiménez-Pulido、Francisco Hueso-Ureña、Tomás Peña-Ruiz、Miguel Quirós-Olozábal、Miguel N. Moreno-Carretero

  DOI：10.1039/c6dt03583c

  日期：——

  determined from spectral and XRD data. The benzodiazepine ligand was reacted with zinc(II), cadmium(II) and mercury(II) chloride, bromide and iodide to give complexes with general formula [M(DLMBZD)X2]. The complexes have been synthesized and characterized by IR, NMR and elemental analysis. The structure of seven complexes has been obtained by single crystal X-ray diffraction. In all the cases, the metal

  2,4-双（1,3,7-三甲基-哌啶-2,4（1 H，3 H）-二酮-6-基）-2,3-二氢-2-甲基-1 H -1,5已制备了苯并二氮杂卓（DLMBZD），并已根据光谱和XRD数据确定了其分子和晶体结构。使苯并二氮杂ligand配体与锌（II），镉（II）和汞（II）氯化物，溴化物和碘化物反应，得到通式为[M（DLMBZD）X 2的配合物]。该配合物已经合成并通过IR，NMR和元素分析表征。通过单晶X射线衍射获得了七个配合物的结构。在所有情况下，金属都是由两个卤化物配体，两个吡嗪环和二氮杂环上的氮原子和一个蝶啶环上的羰基氧（5 + 2）配位的。金属的配位环境是一个基于正方形的金字塔，从Hg（II）到Zn（II）配合物的三角关系不断增加。为了协调金属，配体自身折叠，与嘧啶和吡嗪环建立了四个分子内σ-π相互作用。使用分子中的原子量子理论和配合物的稳定性对电子密度进行了拓扑分析。
• Re(I) and Ag(I) complexes containing the polydentate symmetric diazine derived from 6-acetyl-1,3,7-trimethylpteridine-2,4(1H,3H)-dione in two different binuclear modes
  作者：Sonia B. Jiménez-Pulido、Nuria A. Illán-Cabeza、Francisco Hueso-Ureña、Miguel N. Moreno-Carretero

  DOI：10.1016/j.poly.2012.10.033

  日期：2013.2

  The symmetric diazine derived from 6-acetyl-1,3,7-trimethylpteridine-2,4(1H,3H)-dione, (6,6',1,1'-(hydrazine-1,2-diylidene) bis (ethan-1-yl-1-ylidene) his (1,3,7-trimethylpteridine-2,4(1H,3H)-dione), DHzD) has been prepared and reacted with ReCl(CO)(5) and AgClO4 to give binuclear complexes with formula fRe(2)C(12)(CO)(6)(DHzD)]center dot 2CH(3)CN and [Ag-2(DHzD)(2)](ClO4)(2)center dot 7H(2)O. The XRD single-crystal results indicate two quite different binuclear modes depending on the number of ligands and the counteranion coordinative capacities. Thus, the dirhenium complex consists in two fac-ReCl(CO)(3)(+) units attached to the N5-O4 bidentate sites from both pteridine moieties of the ZZ' isomer of the ligand (Re-O, 2.185(5) and Re-N5, 2.225(6) angstrom). The disilver complex displays two crystallographically independent but practically equivalent 3 + 3-coordinated silver centers to N61, N5 and O4 atoms from both DHzD ligands (E,E' isomer); distances Ag-N range between 2.31 and 2.48 angstrom, whereas oxygen atoms are weaker bonded (2.65-2.82 angstrom). In the molecular units there are not M-M bonds, both metal atoms lying farther than the sum of Van der Waals' radii (Re-Re, 7.959(5) angstrom; Ag-Ag, 4.073(5) angstrom). (C) 2012 Elsevier Ltd. All rights reserved.
• Sachs; Meyerheim, Chemische Berichte, 1908, vol. 41, p. 3964
  作者：Sachs、Meyerheim

  DOI：——

  日期：——