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7-amino-5-(4-(dimethylamino)phenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile

中文名称
——
中文别名
——
英文名称
7-amino-5-(4-(dimethylamino)phenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile
英文别名
7-Amino-5-[4-(dimethylamino)phenyl]-2,4-dioxo-1,5-dihydropyrano[2,3-d]pyrimidine-6-carbonitrile
7-amino-5-(4-(dimethylamino)phenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile化学式
CAS
——
化学式
C16H15N5O3
mdl
——
分子量
325.327
InChiKey
FGSHOKWWGRQVCI-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    0.7
  • 重原子数:
    24
  • 可旋转键数:
    2
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.19
  • 拓扑面积:
    121
  • 氢给体数:
    3
  • 氢受体数:
    6

反应信息

  • 作为反应物:
    描述:
    劳森试剂7-amino-5-(4-(dimethylamino)phenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile乙腈 为溶剂, 反应 6.0h, 以66%的产率得到5-(4-dimethylaminophenyl)-4-imino-2-(4-methoxyphenyl)-2-sulfide-1,5,6,7,8,9-hexahydro-2H,4H-pyrimido[5',4':5,6]pyrano-[2,3-d][1,3,2]thiazaphosphinine-6,8-dione
    参考文献:
    名称:
    有机磷化合物的研究。第 1 部分:一些新的嘧啶并[5',4':5,6]吡喃并[2,3-d][1,3,2]噻唑膦化合物的合成和体外抗菌活性
    摘要:
    2,4-双(4-甲氧基苯基)-1,3,2,4-二硫代二膦烷-2,4-二硫化物(劳森试剂,LR)与吡喃并[2,3-d]嘧啶-2,4-(1H ,3H)-二酮衍生物在沸腾的乙腈中得到各种嘧啶基[5',4':5,6]吡喃并[2,3-d][1,3,2]硫氮膦衍生物。通过元素分析和光谱数据表征了目标化合物的结构。通过圆盘扩散法测试了所有合成化合物对各种微生物的生物活性。总的来说,新合成的化合物对大多数应用的微生物表现出良好的抑制作用。
    DOI:
    10.1002/ardp.201300171
  • 作为产物:
    描述:
    巴比妥酸对二甲氨基苯甲醛丙二腈 在 4,4′-(butane-1,4-diyl)bis(1-sulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium) tetrachloride 作用下, 以 为溶剂, 反应 0.13h, 以93%的产率得到7-amino-5-(4-(dimethylamino)phenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile
    参考文献:
    名称:
    纳米级NS-C 4(DABCO-SO 3 H)2·4Cl催化合成嘧啶并[4,5-d]嘧啶酮和吡喃并[2,3-d]嘧啶酮
    摘要:
    在这项工作中,4,4'-(1-丁烷1,4-丁二)双(1-磺基-1,4-二氮杂双环[2.2.2]辛烷-1,4-二鎓)四氯化物(NS-C 4(DABCO -SO 3 H)2 ·4Cl),一种新报道的纳米级布朗斯台德酸催化剂,用于有效合成嘧啶并[4,5- d ]嘧啶酮和吡喃并[2,3- d ]嘧啶酮衍生物。产物是在温和和环境友好的条件下以极短的反应时间以优异的产率形成的。使用绿色溶剂和简单的方法,无副反应和使用廉价的,负载较低的催化剂是这项工作的其他优点。
    DOI:
    10.1007/s13738-017-1074-4
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文献信息

  • Succinimidinium N-sulfonic acid hydrogen sulfate as an efficient ionic liquid catalyst for the synthesis of 5-arylmethylene-pyrimidine-2,4,6-trione and pyrano[2,3-d]pyrimidinone derivatives
    作者:Masoumeh Abedini、Farhad Shirini、Javad Mohammad-Alinejad Omran、Mohadeseh Seddighi、Omid Goli-Jolodar
    DOI:10.1007/s11164-015-2289-6
    日期:2016.5
    ([SuSA-H]HSO4) as a new ionic liquid is prepared and characterized using a variety of techniques, including infrared spectra (FT-IR), 1H and 13C NMR, scanning electron microscopy, a mass spectra method, as well as by Hammett acidity function. The prepared reagent is efficiently able to catalyze the preparation of 5-arylmethylene-pyrimidine-2,4,6-triones via the condensation of aldehydes and barbituric acid
    使用多种技术制备并表征了琥珀酰亚胺 N- 磺酸硫酸氢盐([SuSA-H] HSO 4),并使用多种技术进行了表征,包括红外光谱(FT-IR),1 H和13 C NMR,扫描电子显微镜,质谱方法以及Hammett酸度函数。通过醛和巴比妥酸的缩合,所制备的试剂能够有效地催化5-芳基亚甲基-嘧啶-2,4,6-三酮的制备。进一步的研究表明,醛与巴比妥酸和丙二腈的缩合反应生成吡喃并[2,3- d 在该试剂的存在下,也可以有效地促进]嘧啶酮衍生物。本发明的方法具有几个优点,包括易于制备和处理催化剂,简单和容易的后处理,短的反应时间,产物的高产率和催化剂的可回收性。
  • Three-component synthesis of 4<i>H</i>-pyran scaffolds accelerated by a gabapentin-based natural deep eutectic solvent
    作者:Meysam Alipour Khoshdel、Farhad Shirini、Mohaddeseh Safarpoor Nikoo Langarudi、Mehdi Zabihzadeh、Mohammad Biglari
    DOI:10.1039/d0nj05342b
    日期:——
    catalyst for the synthesis of 4H-pyran scaffolds such as tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone(thione) derivatives. The use of inexpensive and bio-compatible reagents for the synthesis of the catalyst, a simple and green procedure for the preparation of the catalyst and products, short reaction times, high yields of the products, and applicability to large-scale synthesis are the prominent
    在最近的有机合成中,对环境无害的合成方法的发展引起了越来越多的关注。作为这一概念的一部分,我们的小组使用加巴喷丁和氯化胆碱合成了一种新型的天然深共熔溶剂(NADES)。在通过FTIR,1 H和13 C NMR以及质谱进行表征后,所制备的NADES被用作合成4 H-吡喃骨架如四氢苯并[ b ]吡喃和吡喃并[2,3- d ]的有效催化剂。]嘧啶酮(硫酮)衍生物。廉价的和生物相容性试剂用于催化剂的合成,用于催化剂和产物的制备的简单且绿色的过程,短的反应时间,产物的高产率以及适用于大规模合成是突出的问题。该协议的功能。而且,该催化剂可以容易地回收并循环多达五次,而不会显着损失其催化活性。
  • Cheap thiamine hydrochloride as efficient catalyst for synthesis of 4H-benzo[b]pyrans in aqueous ethanol
    作者:Lu Chen、Sunan Bao、Lixiang Yang、Xian Zhang、Bin Li、Yibiao Li
    DOI:10.1007/s11164-016-2843-x
    日期:2017.7
    Preparation of pharmaceutically active 2-amino-4H-pyran derivatives has been achieved using cheap thiamine hydrochloride as catalyst. A wide range of aromatic aldehydes easily undergo condensation with malononitrile and several kinds of 1,3-cyclohexanedione under mild condition to afford the desired product with good purity in excellent yield. This protocol has various advantages as a simple, clean, and environmentally benign three-component process.
    利用廉价原料盐酸硫胺素作为催化剂,已经实现了具有药理活性的2-氨基-4H-吡喃衍生物的制备。多种芳香醛可以在温和条件下与丙二腈以及几种1,3-环己二酮发生缩合反应,得到纯度高且产率优异的目标产物。该方法作为一个简便、清洁且环境友好的三组分反应,具有多种优势。
  • A study on the physical properties of low melting mixtures and their use as catalysts/solvent in the synthesis of barbiturates
    作者:Letcy Vincent Theresa、Govindan Avudaiappan、Machingal Shaibuna、Kottayil Hiba、Krishnapillai Sreekumar
    DOI:10.1002/jhet.4315
    日期:2021.9
    In recent years, deep eutectic solvents have become attractive due to their interesting characteristics such as, physicochemical properties, low cost of components, easiness to prepare, low toxicity, bio-renewability, and biodegradability. In order to make the deep eutectic mixture more cost-effective and renewable, carbohydrate derivatives were linked with deep eutectic mixtures, since, carbohydrates
    近年来,深共熔溶剂由于其物理化学性质、组分成本低、易于制备、低毒性、生物可再生和生物降解性等有趣特性而变得有吸引力。为了使深共晶混合物更具成本效益和可再生性,碳水化合物衍生物与深共晶混合物相关联,因为碳水化合物是地球上最重要和分布最广的可再生化合物。在这项工作中,我们使用由碳水化合物组成的低熔点混合物来创建有机转化的反应介质。对混合物的密度、粘度、酸度、折射率、表面张力、溶解度、玻璃化转变温度、热稳定性、溶剂极性和毒性等物理性质进行了研究。低熔点混合物被用作反应介质和催化剂以有效合成巴比妥酸盐。醛类与巴比妥酸/硫代巴比妥酸之间的反应,以及醛类、巴比妥酸/硫代巴比妥酸和丙二腈/二甲酮之间的反应均以良好到极好的收率进行。还确定了催化剂/溶剂的可回收性。
  • Efficient synthesis of pyrano[2,3- d ]pyrimidinone and pyrido[2,3- d ]pyrimidine derivatives in presence of novel basic ionic liquid catalyst
    作者:Omid Goli Jolodar、Farhad Shirini、Mohadeseh Seddighi
    DOI:10.1016/s1872-2067(17)62827-4
    日期:2017.7
    ABSTRACT A basic ionic liquid, namely 1,1′-(butane-1,4-diyl)bis(1,4-diazabicyclo [2.2.2]octan-1-ium) hydroxide, was prepared and characterized using Fourier-transform infrared spectroscopy, 1H nuclear magnetic resonance spectroscopy, and pH measurements. The ionic liquid was used for efficient promotion of the synthesis of pyrano[2,3-d]pyrimidinone and pyrido[2,3-d]pyrimidine derivatives at room temperature
    摘要 制备了碱性离子液体,即 1,1'-(丁烷-1,4-二基)双(1,4-二氮杂双环 [2.2.2]octan-1-ium)氢氧化物,并使用傅里叶变换红外光谱对其进行表征。光谱、1H 核磁共振光谱和 pH 测量。该离子液体用于在室温研磨条件下有效促进吡喃并[2,3-d]嘧啶酮和吡啶并[2,3-d]嘧啶衍生物的合成。程序简单、反应时间短、收率高、非柱色谱分离、起始原料的商业可用性和催化剂的可回收性是该方法的吸引人的特征。
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