2-(4-methoxyphenyl)-1,4,5,6-tetrahydropyrimidine | 46313-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)-1,4,5,6-tetrahydropyrimidine
• 英文别名: 2-(4-methoxy-phenyl)-1,4,5,6-tetrahydro-pyrimidine；2-p-Methoxy-phenyl-3,4,5,6-tetrahydro-pyrimidin
• CAS: 46313-35-3
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: GIEKQBSDGMDXJN-UHFFFAOYSA-N

物化性质

• 熔点：
  132-135 °C
• 沸点：
  352.9±34.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-1,4,5,6-tetrahydropyrimidine 在 吡啶 、 sodium hydroxide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 2-(4-甲氧基苯基)嘧啶
  参考文献：
  名称：

  Efficient and Benign One-Pot Conversion of N-Tosyl-1,4,5,6-tetrahydropyrimidines to Pyrimidines via Tandem β-Elimination and Aromatization

  摘要：

  An efficient, mild, benign, and practical method for one-pot conversion of N-tosyl-1,4,5,6-tetrahydropyrimidines into pyrimidines is discussed in detail. In this method, N-tosyl-1,4,5,6-tetrahydropyrimidines are first prepared via N-tosylation of tetrahydropyrimidines with TsCl and then treated with 1.5 equivalents of NaOH in dimethylsulfoxide (DMSO) under air at 60 degrees C to afford corresponding pyrimidines in 70-95% yields via cascade -elimination and aromatization. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resources: Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.764433
• 作为产物：
  描述：

  2-(4-Methoxy-phenyl)-hexahydro-pyrimidine 在 碘 、 potassium carbonate 、 sodium hydroxide 作用下， 以 叔丁醇 、 水 为溶剂， 反应 3.0h， 以1.4 g的产率得到2-(4-methoxyphenyl)-1,4,5,6-tetrahydropyrimidine
  参考文献：
  名称：

  使用四氢嘧啶作为导向基团的Cu（II）介导的氧化性分子间邻CH功能化。

  摘要：

  四氢嘧啶可作为Cu（ii）介导的氧化性芳香族CH官能化中的导向基团，用于将氧或氮选择性引入邻位。

  DOI：

  10.1039/b905586j

文献信息

• EcoFriendly Synthesis of Tetrahydropyrimidine Derivatives in Aqueous Medium Under Ultrasonic Irradiation
  作者：Valasani Koteswara Rao、Boppudi Hari Babu、Kilaru Raveendra Babu、Doddaga Srinivasulu、Chamarthi Naga Raju

  DOI：10.1080/00397911.2011.582218

  日期：2012.11.15

  Abstract A simple, efficient, and ecofriendly procedure was developed for the synthesis of 2-substituted 1,4,5,6-tetrahydropyrimidine derivatives catalyzed by N-bromosuccinimide using ultrasonic irradiation in aqueous medium. Prominent advantages of this new method are good yields, aqueous medium, short reaction times, and easy workup procedure. The compounds were characterized by infrared, NMR, liquid

  摘要 开发了一种简单、高效且环保的方法，用于在水介质中使用超声波辐照 N-溴代琥珀酰亚胺催化合成 2-取代的 1,4,5,6-四氢嘧啶衍生物。这种新方法的突出优点是收率高、使用水性介质、反应时间短、后处理程序简单。通过红外、核磁共振、液相色谱-质谱和元素分析对化合物进行了表征。图形概要
• A novel iodo bridged 1D CuI coordination polymer containing N,N-bidentate Schiff base ligand: Synthesis, structure, theoretical studies, electrochemical properties, and catalytic activity in the synthesis of tetrahydropyrimidines
  作者：Hadi Kargar、Mehdi Fallah-Mehrjardi、Majid Moghadam、Akbar Omidvar、Hamid Reza Zare-Mehrjardi、Necmi Dege、Muhammad Ashfaq、Khurram Shahzad Munawar、Muhammad Nawaz Tahir

  DOI：10.1016/j.poly.2023.116754

  日期：2024.2

  new 1D polymeric Cu(I) complex [Cu(L2Cl)I]n, where L = N,N′-bis(2-chlorobenzylidene)ethane-1,2-diamine, was synthesized and characterized using different analytical approaches, comprising 1H NMR, FT-IR, and CHN analysis. The geometrical features of the complex were determined through the single crystal X-ray diffraction (SC-XRD) method, which revealed that the copper atom is coordinated to the N atoms

  在本研究中，一种新的一维聚合Cu(I)配合物[Cu(L 2Cl )I] n ，其中L = N,N′-双(2-氯亚苄基)乙烷-1,2-二胺采用不同的分析方法进行合成和表征，包括 1 H NMR、FT-IR 和 CHN 分析。通过单晶X射线衍射（SC-XRD）方法确定了配合物的几何特征，表明铜原子与席夫碱的N原子配位。 Cu(I) 离子周围的键角表明该配合物的三角平面几何形状有些扭曲。 Hirshfeld 表面分析 (HSA) 用于研究非共价分子间相互作用，而理论研究则利用 B3P86/Def2-TZVP 理论水平的 DFT 进行。 [Cu(L 2Cl )I] n 的理论结果与实验键长的一致性证实了理论结论的可靠性。为了更好地了解 [Cu(L 2Cl )I] n 的分子间电荷转移特征，还进行了自然键轨道以及分子中的原子分析。在 25 °C 下，使用循环伏安法在 pH 7.0 缓冲溶液中探索了 Cu(I)
• Efficient and Benign One-Pot Conversion of <i>N</i>-Tosyl-1,4,5,6-tetrahydropyrimidines to Pyrimidines via Tandem <font>β</font>-Elimination and Aromatization
  作者：Tien Ha Trieu、Jing Dong、Xiao-Xin Shi、Xia Lu、Qiang Zhang

  DOI：10.1080/00397911.2013.764433

  日期：2013.12.2

  An efficient, mild, benign, and practical method for one-pot conversion of N-tosyl-1,4,5,6-tetrahydropyrimidines into pyrimidines is discussed in detail. In this method, N-tosyl-1,4,5,6-tetrahydropyrimidines are first prepared via N-tosylation of tetrahydropyrimidines with TsCl and then treated with 1.5 equivalents of NaOH in dimethylsulfoxide (DMSO) under air at 60 degrees C to afford corresponding pyrimidines in 70-95% yields via cascade -elimination and aromatization. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resources: Full experimental and spectral details.]
• Cu(ii)-mediated oxidative intermolecular ortho C–H functionalisation using tetrahydropyrimidine as the directing group
  作者：Tsukasa Mizuhara、Shinsuke Inuki、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1039/b905586j

  日期：——

  Tetrahydropyrimidine works efficiently as a directing group in Cu(ii)-mediated oxidative aromatic C-H functionalisation for the selective introduction of oxygen or nitrogen to the ortho-position.

  四氢嘧啶可作为Cu（ii）介导的氧化性芳香族CH官能化中的导向基团，用于将氧或氮选择性引入邻位。