4-(naphthalen-1-yl)-7-(naphthalen-1-ylmethylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one | 1141931-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(naphthalen-1-yl)-7-(naphthalen-1-ylmethylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one
• 英文别名: 4-(naphthalen-1-yl)-7-(naphthalen-1yl-methylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one
• CAS: 1141931-67-0
• 化学式: C₂₈H₂₂N₂O
• 分子量: 402.495
• InChiKey: OHSQBSFPAPZALF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-萘甲醛 、 环戊酮 、 尿素 在 1-butane-sulfonic acid-3-methylimidazolium tosylate 作用下， 反应 0.1h， 以84%的产率得到4-(naphthalen-1-yl)-7-(naphthalen-1-ylmethylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-one
  参考文献：
  名称：

  微波辅助布朗斯台德酸性离子液体通过环戊酮，醛和尿素的三组分偶联促进一锅合成杂双环二氢嘧啶酮

  摘要：

  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）。

  DOI：

  10.1002/jhet.415

文献信息

• Gallium(III) Iodide‐catalyzed Biginelli‐type Reaction Under Solvent‐free Conditions: Efficient Synthesis of Dihydropyrimidine‐2(1 <i>H</i> )‐one Derivatives
  作者：Dapeng Li、Haifeng Mao、Litao An、Zhihao Zhao、Jianping Zou

  DOI：10.1002/cjoc.201090338

  日期：2010.10

  The Biginelli‐type condensation of ethyl acetoacetate/cycloketone, aldehyde and urea/thiourea under solvent‐free condition catalyzed by 10% gallium(III) iodide to form dihydropyrimidine‐2(1H)‐one derivatives was described. This process offered one way to constructing dihydropyrimidine‐2(1H)‐ones in good to excellent yields with simple procedure and short reaction time.

  描述了乙炔乙酸乙酯/环酮，醛和脲/硫脲在无溶剂条件下由10％碘化镓（III）催化形成二氢嘧啶-2（1 H）-一衍生物的Biginelli型缩合反应。该方法提供了一种以良好的收率和良好的产率，简单的方法和较短的反应时间构建二氢嘧啶-2（1 H）-酮的方法。
• 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.
• Ga(OTf)3 Catalyzed Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones
  作者：Jingjing Xia、Kehua Zhang

  DOI：10.3987/com-14-13118

  日期：——

  Gallium(III) triflate was used to catalyze Biginelli-like reactions under solvent-free condition to obtain dihydropyrimidinone derivatives in good to excellent yields and short reaction time.