4-(4-fluorophenyl)-7-[(4-fluorophenyl)methylidene]-3,4,5,6-tetrahydro-1H-cyclopenta[d]pyrimidin-2-one | 861633-18-3

• 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: 4-(4-fluorophenyl)-7-[(4-fluorophenyl)methylidene]-3,4,5,6-tetrahydro-1H-cyclopenta[d]pyrimidin-2-one
• CAS: 861633-18-3
• 化学式: C₂₀H₁₆F₂N₂O
• 分子量: 338.357
• InChiKey: SSRNOSAINKGQTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 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：

  对氟苯甲醛 、 环戊酮 、 尿素 在 nano-TiO₂-SO₃H 作用下， 反应 1.25h， 以83%的产率得到4-(4-fluorophenyl)-7-[(4-fluorophenyl)methylidene]-3,4,5,6-tetrahydro-1H-cyclopenta[d]pyrimidin-2-one
  参考文献：
  名称：

  纳米二氧化钛负载的磺酸：一种有效且可重复使用的催化剂，可在无溶剂条件下用于多种有机反应

  摘要：

  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。

  DOI：

  10.1016/j.catcom.2014.07.002

文献信息

• A Regioselective Biginelli-like Reaction Controlled by the Size of Alicyclic Mono-ketones
  作者：Yu Wan、Rui Yuan、Hua-hong Xu、Chao Wang、Jin-long Qi、Hui Wu

  DOI：10.1002/jhet.1893

  日期：2014.8

  A regioselective Biginelli-like reaction of alicyclic mono-ketones, aromatic aldehydes, and urea in ionic liquid [BPY]BF4 has been investigated. The process is controlled by the size of alicyclic mono-ketones and the steric hindrance of aromatic aldehydes. The reaction of cyclopentanone with urea and aromatic aldehydes afforded 7-arylidene-3,4,6,7-tetrahydro-4-aryl-1H-cyclopenta[d]pyrimidin-2(5H)-ones

  研究了离子液体[BPY] BF 4中脂环族单酮，芳族醛和脲的区域选择性Biginelli样反应。该过程受脂环族单酮的大小和芳族醛的空间位阻的控制。的反应环戊酮与尿素和芳香族醛基反应制得7-亚芳基-3,4,6,7-四氢-4-芳基-1 H-环戊基[d]嘧啶-2（5 H）-ones（）。当在相同条件下使用环己酮作为活性亚甲基的来源与具有少量位阻基团的脲和醛反应时，8-亚芳基-3,4,5,6,7，8-六氢-4-芳基喹唑啉-2（ 1 H）-个（），是 ，而得到4,8-双芳基-tahydro-1 H-嘧啶[5,4 - i ]-喹唑啉-2,10（3 H，11 H）-二酮（）是通过环己酮，尿素和具有高空间位阻基团的芳族醛的简单一锅反应获得的。讨论了可能的过渡状态和区域选择性过程的机制。
• Efficient synthesis of pyrimidinone derivatives by ytterbium chloride catalyzed Biginelli-type reaction under solvent-free conditions
  作者：Huihui Zhang、Zhuqing Zhou、Zhigang Yao、Fan Xu、Qi Shen

  DOI：10.1016/j.tetlet.2009.01.103

  日期：2009.4

  An efficient and clean method was developed for the one-pot synthesis of pyrimidinones by ytterbium chloride catalyzed Biginelli-type reaction of aromatic aldehyde, cyclopentanone, and urea or thiourea under solvent-free conditions.

  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。
• 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。
• Microwave-assisted Brønsted acidic ionic liquid-promoted one-pot synthesis of heterobicyclic dihydropyrimidinones by a three-component coupling of cyclopentanone, aldehydes, and urea
  作者：Matiur Rahman、Adinath Majee、Alakananda Hajra

  DOI：10.1002/jhet.415

  日期：——

  A simple and efficient method has been developed for the synthesis of heterobicyclic dihydropyrimidinone derivatives through a solvent‐free one‐pot three‐component condensation of aromatic aldehydes, cyclopentanone, and urea or thiourea in the presence of Brønsted acidic ionic liquid under microwave irradiation. The catalyst can be reused at least six times without any noticeable decrease in catalytic

  在布朗斯台德酸性离子液体的存在下，在微波辐射下，芳香族醛，环戊酮和尿素或硫脲的无溶剂单锅三组分缩合反应，已开发出一种简单有效的方法来合成杂双环二氢嘧啶酮衍生物。催化剂可以重复使用至少六次，而催化活性不会明显降低。J.杂环化​​学。（2010）。
• An efficient and environmentally friendly procedure for synthesis of pyrimidinone derivatives by use of a Biginelli-type reaction
  作者：Min Lei、Lei Ma、Lihong Hu

  DOI：10.1007/s00706-010-0357-6

  日期：2010.9

  A Biginelli-type three-component reaction involving cyclopentanone, aromatic aldehyde, and urea or thiourea for preparation of pyrimidinone derivatives under neat conditions is described. This condensation reaction can also take place smoothly in the presence of vitamin B(1) in EtOH at 80 A degrees C in good yield. The procedure is simple, high-yielding, time-saving, and environment friendly.