N-[(5-amino-4-cyano-3-phenyl-2,3-dihydrothiophen-2-yl)carbonyl]piperidine-1-carboxamide | 1146596-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: N-[(5-amino-4-cyano-3-phenyl-2,3-dihydrothiophen-2-yl)carbonyl]piperidine-1-carboxamide
• 英文别名: N-(5-amino-4-cyano-3-phenyl-2,3-dihydrothiophene-2-carbonyl)piperidine-1-carboxamide
• CAS: 1146596-05-5
• 化学式: C₁₈H₂₀N₄O₂S
• 分子量: 356.448
• InChiKey: KKNWZKQNCPFYIU-UHFFFAOYSA-N

物化性质

• 熔点：
  223-224 °C
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 以 水 、 PEG 400 为溶剂， 反应 6.17h， 生成 N-[(5-amino-4-cyano-3-phenyl-2,3-dihydrothiophen-2-yl)carbonyl]piperidine-1-carboxamide
  参考文献：
  名称：

  An efficient synthesis of dihydrothiophene ureidoformamides by domino reactions of 1,3-thiazolidinedione under catalyst-free conditions

  摘要：

  通过研究在聚乙二醇400/水体系中，醛、丙二腈、胺和1,3-噻唑烷二酮的串联反应，高效合成了二氢噻吩脲基甲酰胺。该反应无需催化剂和有毒溶剂，反应时间短，产物分离简便，因而更加环保，适合大规模操作。

  DOI：

  10.1039/c0gc00884b

文献信息

• Improved synthesis of dihydrothiophenes derivatives under ultrasound irradiation
  作者：Da-Qing Shi、Yi Zou、Yu Hu、Hui Wu

  DOI：10.1002/jhet.662

  日期：2011.7

  A series of dihydrothiphenes derivatives were synthesized via the four‐component reaction of aldehyde, malononitrile, 1,3‐thiazolidinedione, and piperidine at room temperature under ultrasound irradiation. Compared with the conventional methods, the remarkable advantages of this method are operational simplicity, higher yield, and shorter reaction time. J. Heterocyclic Chem., (2011).

  醛，丙二腈，1,3-噻唑烷二酮和哌啶在室温下超声辐射下的四组分反应合成了一系列二氢噻吩衍生物。与常规方法相比，该方法的显着优点是操作简单，产率更高，反应时间更短。J.杂环化​​学。（2011）。
• Green synthesis of 5-arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium
  作者：Ardeshir Khazaei、Hojat Veisi、Maryam Safaei、Hossein Ahmadian

  DOI：10.1080/17415993.2013.860142

  日期：2014.5.4

  An efficient synthesis of 5-arylidene-2,4-thiazolidinediones and 5-benzylidene rhodanines by the Knoevenagel condensation of 2,4-thiazolidinedione or rhodanine with aromatic aldehydes was studied. It proceeded smoothly in the presence of tetrabutylammonium hydroxide/H O-2-EtOH to afford the corresponding products in high yields at 50 degrees C. Also, a series of dihydrothiophene derivatives were synthesized via the four-component reaction of aldehyde, malonitrile, 2,4-thiazolidinedione, and piperidine in the presence of Bu4NOH as a basic ionic liquid in aqueous medium. This new method offers several advantages, such as excellent yields, short reaction times, and simple procedure.
• Synthesis of Dihydrothiophenes or Spirocyclic Compounds by Domino Reactions of 1,3-Thiazolidinedione
  作者：Jing Sun、Li-Li Zhang、Er-Yan Xia、Chao-Guo Yan

  DOI：10.1021/jo900215a

  日期：2009.5.1

  The domino reactions of 1,3-thiazolidinedione, malononitrile, and aromatic aldehydes in the presence of different organic amines were studied. Secondary amines such as pyrrolidine, piperidine, morpholine, and dimethylamine and primary amines such as benzylamine yield dihydrothiophene derivatives through a domino ring-opening/recyclization reaction of 1,3-thiazolidinedione. Bulky diethylamine, diisopropylamine, and 1,4-diazabicyclo[2.2.2]octane give spirocyclohexano-1,3-thiazole through a double Michael addition/spirocyclization reaction.