7-(4-bromobenzylidene)-4-(4-bromophenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one | 1141931-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 7-(4-bromobenzylidene)-4-(4-bromophenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one
• 英文别名: (4-bromobenzylidene)-4-(4-bromophenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one
• CAS: 1141931-71-6
• 化学式: C₂₀H₁₆Br₂N₂O
• 分子量: 460.168
• InChiKey: AHQQIQIDPKBZFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  41.13
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 、 环戊酮 、 尿素 在 ytterbium(III) chloride 作用下， 反应 4.0h， 以74%的产率得到7-(4-bromobenzylidene)-4-(4-bromophenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one
  参考文献：
  名称：

  无溶剂条件下氯化催化Biginelli型反应有效合成嘧啶酮衍生物

  摘要：

  开发了一种高效清洁的方法，用于在无溶剂条件下通过氯化催化芳香族醛，环戊酮，尿素或硫脲的Biginelli型反应进行一锅法合成嘧啶酮。

  DOI：

  10.1016/j.tetlet.2009.01.103

文献信息

• Application of O-sulfonic acid poly(4-vinylpyrrolidonium) chloride as an efficient polymer-supported catalyst in the rapid synthesis of 2H-indazolo[2,1-b]phthalazine-triones and Biginelli-like products
  作者：Seyedeh Zahra Dalil Heirati、Farhad Shirini、Abdollah Fallah Shojaei

  DOI：10.1007/s13738-020-01982-3

  日期：2020.12

  used as a catalyst for the synthesis of a series of 2H-indazolo[2,1-b]phthalazine-triones and Biginelli-like products. It was observed that only 10 mg of the catalyst was enough to catalyze these reactions under mild conditions, and the corresponding products were obtained in high to excellent yields. Moreover, the catalyst could be repeatedly used for at least five times without a noticeable decrease

  在这项工作中，使用O-磺酸聚（4-乙烯基吡咯烷鎓）氯化物（[PVP-SO]首次有效地合成了一系列2 H-吲唑并[2,1-b]邻苯二嗪三酮和类似Biginelli的产物。3 H] Cl）作为环保型聚合物负载型催化剂。首先，根据氯磺酸的量和磺化时间对催化剂的制备工艺进行优化，以得到最大酸度的催化剂。获得的[PVP-SO 3 H] Cl的最大酸度为3.31 mmol g -1。然后，将优化的[PVP-SO 3 H] Cl用作合成一系列2 H的催化剂-吲唑并[2,1-b]酞嗪三酮类和Biginelli样产品。观察到仅10mg的催化剂足以在温和的条件下催化这些反应，并且以高至优异的产率获得了相应的产物。此外，该催化剂可以重复使用至少五次而其催化活性没有明显降低。
• Nano titania-supported sulfonic acid: An efficient and reusable catalyst for a range of organic reactions under solvent free conditions
  作者：Salman Rahmani、Ali Amoozadeh、Eskandar Kolvari

  DOI：10.1016/j.catcom.2014.07.002

  日期：2014.11

  gravimetric analysis (TGA). The catalytic activity of n-TSA was investigated in the synthesis of important organic derivatives such as pyrimidones, benzothiazoles and chalcones. All of the reactions are very fast and the yields are good to excellent. The catalyst was easily separated and reused for several runs without appreciable loss of its catalytic activity.

  纳米二氧化钛负载的磺酸（n-TSA）可以很容易地由纳米二氧化钛（氧化钛）与氯磺酸作为磺化剂的反应制得，并通过FT-IR光谱，扫描电子显微镜（SEM）和X射线进行表征衍射（XRD）和热重分析（TGA）。在合成重要的有机衍生物（如嘧啶酮，苯并噻唑和查耳酮）中，研究了n-TSA的催化活性。所有的反应都非常快，收率良好至极好。催化剂易于分离，可重复使用几次，而不会明显降低其催化活性。
• PEG-SANM nanocomposite: a new catalytic application towards clean and highly efficient Biginelli-like reaction under solvent-free conditions
  作者：Seyedeh Zahra Dalil Heirati、Farhad Shirini、Abdollah Fallah Shojaei

  DOI：10.1039/c6ra11201c

  日期：——

  A series of pyrimidinone derivatives were efficiently synthesized using PEG-SANM nanocomposite as the solid acid nanocatalyst under mild and solvent-free conditions. The generality of the process was successfully demonstrated by variation of the starting materials. Also, large-scale synthesis of products occurred readily in the presence of this nanocatalyst. This new method eliminated the use of organic

  以PEG-SANM纳米复合材料为固体酸纳米催化剂，在温和无溶剂条件下有效合成了一系列嘧啶酮衍生物。通过改变起始原料成功地证明了该方法的一般性。而且，在这种纳米催化剂的存在下，容易发生大规模的产物合成。这种新方法省去了有机溶剂的使用，在较短的反应时间内进行简单的后处理即可获得高至优异的收率和高纯度的产物。无需色谱分离即可分离获得的产物。回收纳米催化剂并重复使用多达五次，而催化活性没有明显降低。
• Three-component one-pot synthesis of pyrimidinone derivatives in fluorous media: Ytterbium bis(perfluorooctanesulfonyl)imide complex catalyzed Biginelli-type reaction
  作者：Mei Hong、Chun Cai

  DOI：10.1002/jhet.241

  日期：2009.11

  The condensation of aromatic aldehyde, cyclopentanone, and urea or thiourea in the presence of Ytterbium bis(perfluorooctanesulfonyl)imide complex in perfluorodecalin was used to synthesize a variety of benzylidene heterobicyclic pyrimidinones in excellent yields. J. Heterocyclic Chem., (2009).

  在全氟萘烷中的双（全氟辛烷磺酰基）酰亚胺Y配合物存在下，芳香醛，环戊酮和脲或硫脲的缩合反应可用于合成各种亚苄基杂环双环嘧啶酮。J.杂环化​​学，（2009）。
• Brønsted Acidic Ionic Liquid as an Efficient and Reusable Catalyst for One-Pot, Three-Component Synthesis of Pyrimidinone Derivatives via Biginelli-Type Reaction Under Solvent-Free Conditions
  作者：Abdol R. Hajipour、Yosof Ghayeb、Nafisehsadat Sheikhan、Arnold E. Ruoho

  DOI：10.1080/00397911.2010.501474

  日期：2011.8

  cyclopentanone and urea or thiourea in the presence of N-(4-sulfonic acid) butyl triethyl ammonium hydrogen sulfate ([TEBSA][HSO4]) as the Brønsted acidic ionic liquid and effective catalyst under thermal and solvent-free conditions. Good yields, short reaction times, straightforward workup, reusability of the catalyst, and green conditions are the most obvious advantages of this procedure.

  摘要 在 N-(4-磺酸) 丁基三乙基硫酸氢铵 ([TEBSA][HSO4 ]) 作为 Brønsted 酸性离子液体和在热和无溶剂条件下的有效催化剂。良好的收率、较短的反应时间、简单的后处理、催化剂的可重复使用性和绿色条件是该程序最明显的优势。