7-(4-cyanobenzylidene)-4-(4-cyanophenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one | 1141931-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-(4-cyanobenzylidene)-4-(4-cyanophenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one
• 英文别名: 4-[[4-(4-cyanophenyl)-2-oxo-3,4,5,6-tetrahydro-1H-cyclopenta[d]pyrimidin-7-ylidene]methyl]benzonitrile
• CAS: 1141931-74-9
• 化学式: C₂₂H₁₆N₄O
• 分子量: 352.395
• InChiKey: BEWMCKUSDCBCJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.71
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  环戊酮 、 4-氰基苯甲醛 、 尿素 在 potassium phtalimide 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以92%的产率得到7-(4-cyanobenzylidene)-4-(4-cyanophenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one
  参考文献：
  名称：

  邻苯二甲酰亚胺钾：一种高效的绿色有机催化剂，在溶剂下合成4-芳基-7-（芳基亚甲基）-3,4,6,7-四氢-1H-环戊[d]嘧啶-2（5H）-一个/硫酮无条件

  摘要：

  摘要报道了使用邻苯二甲酰亚胺钾作为绿色，温和且可商购的有机催化剂，在环戊酮，醛和尿素/硫脲的一锅多组分环缩合反应中高效合成Biginelli型化合物的方法。本方法学是访问4-芳基-7-（芳基亚甲基）-3,4,6,7-四氢-1H-环戊[d]嘧啶-2（5H）-酮/硫酮的绿色方法。它具有多种优点，例如操作步骤简单，不使用危险的有机溶剂以及廉价且环保的固体碱性催化剂。

  DOI：

  10.1016/j.cclet.2013.11.042

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。
• Synthesis of Substituted Pyrimidinones Catalyzed by Boric Acid and Glycerol in Aqueous Medium
  作者：Chhanda Mukhopadhyay、Arup Datta

  DOI：10.1080/00397911.2011.602497

  日期：2013.1

  An expeditious one-pot synthesis of substituted pyrimidinone derivatives with aromatic aldehydes, cyclopentanone, and urea (or thiourea) was developed with boric acid (10 mol%) and glycerol (0.1 mL) in aqueous medium at 45-50 degrees C. The methodology is simple, highly efficient, and high yielding. The idea behind this methodology is that boric acid, being a weak acid, behaves as a strong acid in presence of glycerol in aqueous medium.
• 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.