ethyl 6-methyl-4-(naphthalen-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 6-methyl-4-(naphthalen-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 5-(ethoxycarbonyl)-6-methyl-4-(naphthalen-2-yl)-3,4-dihydropyrimidin-2(1H)-one；Ethyl 6-methyl-4-(naphthalen-2-yl)-2-oxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate；ethyl 6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: RFHBCADEWPPBRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-methyl-4-(naphthalen-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 2,4-二硝基苯肼 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Heterogenized hybrid catalyst of 1-sulfonic acid-3-methyl imidazolium ferric chloride over NaY zeolite for one-pot synthesis of 2-amino-4-arylpyrimidine derivatives: A viable approach

  摘要：

  A new hybrid material of NaY zeolite supported 1-sulfonic acid-3-methyl imidazolium ferric chloride [Msim][FeCl4] has been developed by modifying the zeolite surface with six different w/w ratios through wet impregnation method. These composites were fully characterized by Powder XRD, FT-IR, Raman, TGA, SEM, TEM, EDX, BET, ICP-OES and Hammett acid strength measurement methods. The zeolite framework was found to be remaining preserved up to w/w ratio of 0.2 with some portion of extra framework Al species (EFAI) while crystallinity of the composites decreased from lower to higher loading. The overall thermal stability of composite materials increases up to w/w ratio of 0.1 than NaY. The catalytic performance of composite materials were examined for the novel one-pot consecutive formation of Biginelli- 3,4-dihydropyrimidin-2-(1H)-ones to 2-amino-4-arylpyrimidines. The 0.1 ratio composite material showed excellent catalytic activity up to ten consecutive cycles in solvent-free medium under the optimized reaction condition. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2016.06.015
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2-萘甲醛 、 尿素 在 triphenyl bismuth(V) bisperfluorooctanesulfonate 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以91%的产率得到ethyl 6-methyl-4-(naphthalen-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  空气稳定的双氟辛烷磺酸（V）双氟辛烷磺酸盐是合成含氮化合物的高效催化剂

  摘要：

  三全氟辛烷磺酸三苯基铋是一种对空气和水稳定的路易斯酸。在温和条件下，它对合成氮杂环（如二吲哚基甲烷衍生物，二氢嘧啶酮，二氢吡啶和1,2-二取代的苯并咪唑）具有很高的催化效率。此外，在五个周期的测试中，它可以重复使用而不会失去活性。该催化体系为合成含氮化合物提供了一种简单而有效的方法。

  DOI：

  10.1002/adsc.201500998

文献信息

• One Pot Synthesis of Micromolar BACE-1 Inhibitors Based on the Dihydropyrimidinone Scaffold and Their Thia and Imino Analogues
  作者：Jessica Bais、Fabio Benedetti、Federico Berti、Iole Cerminara、Sara Drioli、Maria Funicello、Giorgia Regini、Mattia Vidali、Fulvia Felluga

  DOI：10.3390/molecules25184152

  日期：——

  A library of dihydropyrimidinones was synthesized via a “one-pot” three component Biginelli reaction using different aldehydes in combination with β-dicarbonyl compounds and urea. Selected 2-thiooxo and 2-imino analogs were also obtained with the Biginelli reaction from thiourea and guanidine hydrochloride, respectively. The products were screened in vitro for their β-secretase inhibitory activity. The majority of the compounds resulted to be active, with IC50 in the range 100 nM–50 μM.

  通过使用不同的醛与β-二羰基化合物和尿素的“一锅法”三组分Biginelli反应合成了一系列二氢嘧啶酮类化合物。选择性地，也从硫脲和盐酸胍得到了2-硫氧代和2-亚氨基类似物。这些产物在体外被筛选，用于评估它们的β-分泌酶抑制活性。大多数化合物表现出活性，IC50在100 nM至50 μM范围内。
• General solvent-free ionic liquid catalyzed C–N/C–C coupled cyclization to diverse dihydropyrimidinones and new organic materials: Langmuir–Blodgett film study
  作者：Swapan Majumdar、Jhinuk De、Ajitesh Pal、Indra Ghosh、Ranendu K. Nath、Sandip Chowdhury、Dipanwita Roy、Dilip K. Maiti

  DOI：10.1039/c5ra01618e

  日期：——

  An ionic liquid catalyzed dual C–N/C–C coupled cyclization under solvent-free green conditions to DHPMs and their innovative new organic materials by LB film study are demonstrated.

  一种离子液体催化的双C-N/C-C偶联环化反应在无溶剂绿色条件下合成了DHPMs及其创新的新有机材料，通过LB膜研究进行了展示。
• [bmim(SO 3 H)][OTf]/[bmim][X] and Zn(NTf 2 ) 2 /[bmim][X] (X = PF 6 and BF 4 ); efficient catalytic systems for the synthesis of tetrahydropyrimidin-ones (-thiones) via the Biginelli reaction
  作者：Hemantkumar M. Savanur、Rajesh G. Kalkhambkar、Gopalakrishnan Aridoss、Kenneth K. Laali

  DOI：10.1016/j.tetlet.2016.05.103

  日期：2016.7

  facile, high yielding, and simple method for the synthesis of a library of dihydropyrimidinones (and -thiones) via the one-pot Biginelli reaction of aldehydes is reported. The method employs the Brønsted acidic IL [bmim(SO3H][OTf] or Zn(NTf2)2 as catalyst along with the readily available imidazolium-ILs as solvent, and exhibits good potential for the recycling and reuse of the IL solvent.

  报道了一种通过醛的一锅Biginelli反应合成二氢嘧啶酮（和-硫酮）文库的简便，高产率和简单的方法。该方法采用布朗斯台德酸性IL [bmim（SO 3 H] [OTf]或Zn（NTf 2）2作为催化剂，并使用易获得的咪唑类ILs作为溶剂，并具有回收和再利用IL溶剂的良好潜力。 。
• Air‐stable zirconium (IV)‐salophen perfluorooctanesulfonate as a highly efficient and reusable catalyst for the synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐ones/thiones under solvent‐free conditions
  作者：Ningbo Li、Yijun Wang、Feijun Liu、Xin Zhao、Xinhua Xu、Quan An、Keming Yun

  DOI：10.1002/aoc.5454

  日期：2020.3

  An air‐stable complex of zirconium (IV)‐salophen perfluorooctanesulfonate (1) was successfully synthesized by reacting Zr (salphen)Cl2 and C8F17SO3Ag. Complex 1 was characterized and studied by different techniques (NMR, IR, HRMS, TG‐DSC, conductivity and acidity measurements), and was found to be air‐stable, water tolerant, thermally stable and strongly Lewis‐acidic. Complex 1 exhibited high catalytic

  通过使Zr（salphen）Cl 2与C 8 F 17 SO 3 Ag反应成功合成了一种空气稳定的锆（IV）-salophen全氟辛烷磺酸盐（1）。配合物1通过不同的技术（NMR，IR，HRMS，TG-DSC，电导率和酸度测量）进行了表征和研究，被发现具有空气稳定性，耐水性，热稳定性和强路易斯酸性。络合物1在无溶剂条件下通过醛，1,3-二羰基化合物和脲/硫脲的Biginelli反应合成3,4-二氢嘧啶-2-（1H）-酮/硫酮具有很高的催化效率。此外，复数1可以重复使用5次，而催化效率的变化却很小。与以前报道的方法相比，该方案的重要特征是无溶剂条件，反应时间短，底物相容性广，效率高和可重复使用性好。
• Polyvinylsulfonic Acid: An Efficient, Water-Soluble and Reusable Brønsted Acid Catalyst for the Three-Component Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones in Water and Ethanol
  作者：Ali Rahmatpour

  DOI：10.1007/s10562-012-0873-6

  日期：2012.12

  environmentally benign protocol has been developed for the one-pot three-component synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones from the cyclocondensation reaction of aldehyde, ethyl acetoacetate (β-dicarbonyl compound) and urea or thiourea using polyvinylsulfonic acid as a reusable homogeneous Brønsted acid- and metal-free organocatalyst in water and ethanol. This new protocol has the advantages

  已经开发了一种简便且环境友好的方案，用于从醛、乙酰乙酸乙酯（β-二羰基化合物）和尿素的环缩反应中一锅三组分合成 3,4-二氢嘧啶-2(1H)-酮/硫酮或硫脲，使用聚乙烯磺酸作为可重复使用的均质布朗斯台德酸和无金属有机催化剂，在水和乙醇中。该新方案具有催化剂易得、稳定、可重复使用和环保、产率高至极好、实验和后处理程序简单等优点。