phenyl(4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methanone | 1166821-21-1

• 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: phenyl(4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methanone
• 英文别名: 4-phenyl-5-phenylmethanone-yl-3,4-dihydropyrimidine-2(1H)-thione；phenyl-(4-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl)methanone
• CAS: 1166821-21-1
• 化学式: C₁₇H₁₄N₂OS
• 分子量: 294.377
• InChiKey: RPEHXCJIWISJJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  73.2
• 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 在 iron(III) chloride 、 三甲基氯硅烷 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 phenyl(4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methanone
  参考文献：
  名称：

  Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions

  摘要：

  Highly stereoselective synthesis of Z-enaminones bearing reactive secondary amino group has been successfully performed in water using tertiary amino group functionalized enaminones under ambient conditions. An interesting promotion effect of water on the reaction via hydrolysis-dehydration condensation has been observed through a designed isotope labeling experiment. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.715712

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。
• Solvent-free synthesis of 6-unsubstituted dihydropyrimidinones using 2-pyrrolidonium bisulphate as efficient catalyst
  作者：Heshmatollah Alinezhad、Mahmood Tajbakhsh、Mahboobeh Zare、Mahbooeh Mousavi

  DOI：10.1515/chempap-2016-0048

  日期：2016.1.1

  A one-pot three-component Biginelli-like reaction of enaminones, aldehydes with urea/thiourea in the presence of 2-pyrrolidonium bisulphate as an acidic ionic liquid catalyst for the preparation of 6-unsubstituted dihydropyrimidinones is described. The excellent yield, short reaction time, simple procedure and avoidance of the use of organic solvents are some advantages of this method.

  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。
• 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。
• Novel four-component reaction towards diastereoselective synthesis of tetrahydropyrimidinthiones
  作者：Jie-Ping Wan、Chunping Wang、Yuanjiang Pan

  DOI：10.1016/j.tet.2010.12.011

  日期：2011.2

  The first multicomponent synthesis of tetrahydropyrimidinthiones has been realized via the four-component assembly of aromatic aldehyde, enaminone, aromatic amine, and thiourea. The reaction was performed at room temperature and the products were obtained in excellent diastereoselectivity. (C) 2010 Elsevier Ltd. All rights reserved.
• Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions
  作者：Yunyun Liu、Rihui Zhou、Jie-Ping Wan

  DOI：10.1080/00397911.2012.715712

  日期：2013.9.17

  Highly stereoselective synthesis of Z-enaminones bearing reactive secondary amino group has been successfully performed in water using tertiary amino group functionalized enaminones under ambient conditions. An interesting promotion effect of water on the reaction via hydrolysis-dehydration condensation has been observed through a designed isotope labeling experiment. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.