5-ethoxycarbonyl-6-methyl-4-(6-methyl-4-oxo-4H-1-benzopyran-3-yl)-3,4-dihydroxypyrimidin-2(1H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-ethoxycarbonyl-6-methyl-4-(6-methyl-4-oxo-4H-1-benzopyran-3-yl)-3,4-dihydroxypyrimidin-2(1H)-one
• 英文别名: ethyl 6-methyl-4-(6-methyl-4-oxo-4H-chromen-3-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 6-methyl-4-(6-methyl-4-oxo-chromen-3-yl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate；ethyl 6-methyl-4-(6-methyl-4-oxochromen-3-yl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: XOCIJIFBUSBYKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酸对甲酚酯 在 aluminum (III) chloride 、 草酰氯 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-ethoxycarbonyl-6-methyl-4-(6-methyl-4-oxo-4H-1-benzopyran-3-yl)-3,4-dihydroxypyrimidin-2(1H)-one
  参考文献：
  名称：

  新型取代的4 H -chromen-1,2,3,4-四氢嘧啶-5-羧酸酯的合成，构效关系作为潜在的抗分枝杆菌和抗癌药

  摘要：

  合成了一系列4 H -1,2,3,4-四氢嘧啶-5-羧甲基铬衍生物7a - 7zb，8a - 8d和9a - 9d并筛选了其对结核分枝杆菌H 37 Rv的体外抗分枝杆菌活性。（MTB）和针对三种人类癌细胞系（包括A549，SK-N-SH和HeLa）的细胞毒性。结果表明，六种化合物的效价更高，而7za与标准药物乙胺丁醇和环丙沙星相比，它是最有效的抗分枝杆菌衍生物。但是，有12种化合物对人神经母细胞瘤细胞系表现出细胞毒性。其中，与标准药物阿霉素相比，化合物7v最有效。这是首次针对这种新型的4 H -chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylates分配体外抗分枝杆菌，抗癌和结构-活性关系的报告。

  DOI：

  10.1016/j.bmcl.2011.03.079

文献信息

• Simple and ecofriendly synthesis of dihydropyrimidinones (thiones), dihydropyridines, and pyridines using 3-formylchromones as substrates assisted by a recyclable Preyssler heteropolyacid
  作者：Laura M. Sanchez、Gustavo Pasquale、Ángel Sathicq、Diego Ruiz、Jorge Jios、Andrea L. Ferreira de Souza、Gustavo P. Romanelli

  DOI：10.1002/hc.21340

  日期：2016.9

  Several dihydropyrimidinones/thiones, 1,4-dihydropyridines, and pyridine derivatives were prepared in very good yields and purity values. The corresponding reactions were carried out by employing a bulk Preyssler heteropolyacid H14[NaP5W29MoO110] as an efficient and recyclable catalyst. The preparation of pyridine derivatives was carried out not through a usual procedure, i.e., the opening of the γ-pyrone

  以非常好的产率和纯度值制备了几种二氢嘧啶酮/硫酮、1,4-二氢吡啶和吡啶衍生物。相应的反应是通过使用本体 Preyssler 杂多酸 H14[NaP5W29MoO110] 作为有效且可回收的催化剂进行的。吡啶衍生物的制备不是通过通常的程序进行的，即3-甲酰基色酮的γ-吡喃酮环的开环。通常，反应在 80°C 的无溶剂条件下进行，反应时间很短。
• Bandyopadhyay, Chandrakanta; Nag, Partha Pratim; Sur, Kumar Ranabir, Journal of the Indian Chemical Society, 2004, vol. 81, # 2, p. 132 - 136
  作者：Bandyopadhyay, Chandrakanta、Nag, Partha Pratim、Sur, Kumar Ranabir、Patra, Ranjan、Banerjee, Subhabrata、Sen, Arunabha、Ghosh, Tapas

  DOI：——

  日期：——
• Sulphated silica tungstic acid as a highly efficient and recyclable solid acid catalyst for the synthesis of tetrahydropyrimidines and dihydropyrimidines
  作者：Nayeem Ahmed、Zeba N. Siddiqui

  DOI：10.1016/j.molcata.2014.02.019

  日期：2014.6

  For the first time sulphated silica tungstic acid (SSTA) has been synthesized and used as an acidic catalyst in organic synthesis. The catalyst was prepared by a simple method based on the reaction of silica with SOCl2 followed by addition of sodium tungstate and then functionalization with chlorosulfonic acid. The three-component Biginelli-like condensation of different heteroaldehydes, urea and ethyl cyanoacetate or phenyl acetic acid catalyzed by SSTA under solvent-free conditions afforded novel tetrahydropyrimidines in high yields. The catalyst tolerated different heteroaldehydes and also catalyzed the synthesis of Biginelli compounds efficiently giving excellent yield of products. The catalyst was characterized by FT-IR, XRD and SEM-EDX analyses. The stability of the catalyst was evaluated by DSC and TG analyses. The major advantages of the present method are high yields, short reaction times, and solvent-free reaction conditions. The activity and simple recyclability without losing catalytic activity make this catalyst a good replacement to literature methods.(c) 2014 Elsevier B.V. All rights reserved.
• Synthesis, structure–activity relationship of novel substituted 4H-chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylates as potential anti-mycobacterial and anticancer agents
  作者：B. China Raju、R. Nageswara Rao、P. Suman、P. Yogeeswari、D. Sriram、Thokhir Basha Shaik、Shasi Vardhan Kalivendi

  DOI：10.1016/j.bmcl.2011.03.079

  日期：2011.5

  neuroblastoma cell line; amongst them the compound 7v is most effective compared to the standard drug Doxorubicin. This is the first report assigning in vitro anti-mycobacterial, anticancer and structure–activity relationship for this new class of 4H-chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylates.

  合成了一系列4 H -1,2,3,4-四氢嘧啶-5-羧甲基铬衍生物7a - 7zb，8a - 8d和9a - 9d并筛选了其对结核分枝杆菌H 37 Rv的体外抗分枝杆菌活性。（MTB）和针对三种人类癌细胞系（包括A549，SK-N-SH和HeLa）的细胞毒性。结果表明，六种化合物的效价更高，而7za与标准药物乙胺丁醇和环丙沙星相比，它是最有效的抗分枝杆菌衍生物。但是，有12种化合物对人神经母细胞瘤细胞系表现出细胞毒性。其中，与标准药物阿霉素相比，化合物7v最有效。这是首次针对这种新型的4 H -chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylates分配体外抗分枝杆菌，抗癌和结构-活性关系的报告。