4-phenyl-5-phenylmethanone-yl-3,4-dihydropyrimidine-2(1H)-one | 1166821-42-6

• 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: 4-phenyl-5-phenylmethanone-yl-3,4-dihydropyrimidine-2(1H)-one
• 英文别名: 5-benzoyl-3,4-dihydro-4-phenylpyrimidin-2(1H)-one；5-benzoyl-4-phenyl-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 1166821-42-6
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: PJPZYDSTAFDMJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-phenyl-3-dimethylaminoprop-2-enone 、 苯甲醛 、 尿素 在 1.    2-pyrrolidon-1-ium hydrogen sulfate 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以92%的产率得到4-phenyl-5-phenylmethanone-yl-3,4-dihydropyrimidine-2(1H)-one
  参考文献：
  名称：

  使用2-吡咯烷鎓硫酸氢盐作为有效催化剂的无溶剂合成6-未取代的二氢嘧啶酮

  摘要：

  描述了在2-吡咯烷鎓硫酸氢盐作为酸性离子液体催化剂的存在下，烯胺酮，醛与脲/硫脲的一锅三组分类似Biginelli的反应，用于制备6-未取代的二氢嘧啶酮。该方法的优点是产率高，反应时间短，操作简单并且避免使用有机溶剂。

  DOI：

  10.1515/chempap-2016-0048

文献信息

• Phenylphosphinic acid-catalyzed synthesis of 6-unsubstituted dihydropyrimidinones under solvent-free conditions
  作者：Heshmatollah Alinezhad、Mahmood Tajbakhsh、Mahboobeh Zare、Mahboobeh Mousavi

  DOI：10.1002/hc.21327

  日期：2016.9

  Phenylphosphinic acid is found to catalyze the three-component condensation of an aldehyde, enaminone, and urea or thiourea to afford the corresponding 6-unsubstituted dihydropyrimidinones in high to excellent yields. This methodology is simple and fast synthetic route for the preparation of interesting class of heterocycles.

  发现苯基次膦酸催化醛、烯胺酮和脲或硫脲的三组分缩合反应，以高产率至极好的产率提供相应的 6-未取代二氢嘧啶酮。该方法是制备感兴趣的杂环类的简单快速的合成路线。
• Chemo-/regioselective synthesis of 6-unsubstituted dihydropyrimidinones, 1,3-thiazines and chromones via novel variants of Biginelli reaction
  作者：Jie-Ping Wan、Yuan-Jiang Pan

  DOI：10.1039/b901112a

  日期：——

  A novel and facile cascade Biginelli-like assembly employing enaminone, aldehyde and urea/thiourea has been developed, which provides a highly chemo- and regioselective synthesis of new dihydropyrimidinones, 1,3-thiazines and chromones by altering particular functional groups in the reactants.

  开发了一种新颖且简便的级联Biginelli类似反应，采用了烯酰胺、醛和尿素/硫脲，通过改变反应物中的特定官能团，实现了新型二氢嘧啶酮、1,3-噻嗪和色酮的高度化学选择性和区位选择性合成。
• A green approach for the multicomponent synthesis of polyhydroquinolines and 6-unsubstituted dihydropyrimidinones using novel highly proficient acidic ionic liquid [CEMIM][MSA] as a reusable catalyst
  作者：Priyanka Patil、Suresh Kadam、Dayanand Patil、Paresh More

  DOI：10.1016/j.catcom.2022.106500

  日期：2022.10

  Carboxylic acid functionalized imidazolium based novel acidic ionic liquid [CEMIM][MSA] was synthesized using economically feasible raw materials under very mild condition. The cost effective and sustainable synthesis of polyhydroquinoline and 6-unsustituted dihydropyrimidinone derivatives in green media was first time carried out very effectively using [CEMIM][MSA] catalyst. Acidic ionic liquid catalyst

  采用经济可行的原料，在非常温和的条件下合成了羧酸官能化咪唑基新型酸性离子液体[CEMIM][MSA]。首次使用 [CEMIM][MSA] 催化剂非常有效地在绿色介质中进行了具有成本效益且可持续的多氢喹啉和 6-未取代的二氢嘧啶酮衍生物合成。具有羧酸基团的酸性离子液体催化剂[CEMIM][MSA]易于分离并重复使用多达五个循环，而其催化活性和稳定性没有太大损失。引入的催化剂在水性介质中表现出更好的催化性能，可以在更短的时间内以优异的收率获得所述化合物。
• Dihydropyrimidones and pharmaceutical compositions thereof
  申请人：King Abdulaziz University

  公开号：US10358425B1

  公开（公告）日：2019-07-23

  A series of heterocyclic compounds containing a dihydropyrimidone or dihydropyrimidinthione functionality. Pharmaceutical compositions containing the compounds and methods of producing the compounds via ultrasonication are also provided.

  一系列含有二氢嘧啶酮或二氢嘧啶酮官能团的杂环化合物。此外，还提供了含有这些化合物的药物组合物以及通过超声波生产这些化合物的方法。
• A One-Pot Biginelli Synthesis of 6-Unsubstituted 5-Aroylpyrimidin-2(1H)-ones and 6-Acetyl-1,2,4-triazin-3(2H)-ones
  作者：Elham Sayed Darwish、Ismail Abdelshafy Abdelhamid、Miead Adel Nasra、Fathy Mohamed Abdel-Gallil、Daisy Hanna Fleita

  DOI：10.1002/hlca.200900355

  日期：——

  AbstractThe three‐component Biginelli‐like cyclocondensation reaction of enamines 1, urea, and aldehydes in dioxane/acetic acid efficiently afforded the corresponding 6‐unsubstituted 3,4‐dihydropyrimidin‐2(1H)‐ones 2 in good yields (Scheme 1, Table). The corresponding reaction of azaenamine (=hydrazone) 7 with benzaldehyde and urea afforded 6‐acetyl‐1,2,4‐triazin‐3(2H)‐ones in good yields (Scheme 3).