5-cyano-4-furan-2-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester | 94640-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-cyano-4-furan-2-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
• 英文别名: ethyl 3-cyano-4-(furan-2-yl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 94640-19-4
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: AUCSFFLGBVKTPS-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C(Solv: ethanol (64-17-5))
• 沸点：
  515.6±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-cyano-4-furan-2-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 为溶剂， 100.0 ℃ 、268.9 kPa 条件下， 反应 0.08h， 以90%的产率得到ethyl 5-cyano-4-(furan-2-yl)-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  具有血管舒张活性的3-氰基-2-吡啶酮衍生物的合成，离体和计算机模拟研究

  摘要：

  描述了通过3,4-二氢吡啶-2--2-氧化方法有效而简单地合成3-氰基-2-吡啶酮衍生物（6a – f）。通过以H 2 SO 4为催化剂源和微波辐射在水介质中重排4 H-吡喃（4a - f）衍生物，还开发了一种更环保的3,4-二氢吡啶-2-酮合成方法。3-氰基-2-吡啶酮衍生物（6a – f）在去甲肾上腺素（0.1μM）预收缩的分离的胸主动脉大鼠环上有或没有内皮（分别为+ E和-E）证明。所有化合物均表现出显着的浓度依赖性和内皮依赖性血管舒张作用，其中硝基衍生物（6a和f）和化合物6d最有效，EC 50分别为7、4.4和5μM。最后，将先前描述的人L型钙通道（LCC）中心孔的3D模型修改为与亚基α-1F亚型1的NCBI序列NP_005174.2一致，将其用于对接大多数活性化合物。6a，d和f发现最低的亲和能结构停靠在由IS6，IS5，IP和IIS6螺旋线相符的同一个空腔中。在由IIS6，I

  DOI：

  10.1016/j.ejmech.2013.10.018
• 作为产物：
  描述：

  (4R)-6-氨基-5-氰基-4-呋喃-2-基-2-甲基-4H-吡喃-3-羧酸乙酯 在 水 、 对甲苯磺酸 作用下， 反应 3.0h， 以85%的产率得到5-cyano-4-furan-2-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media

  摘要：

  A green and highly efficient protocol has been developed for the synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and a 1,3-diketo compound using nano structured ZnO as the catalyst in aqueous alcoholic medium. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran derivatives in aqueous medium applying p-TSOH as the right catalyst source. A wide spectrum of functional groups was tolerated in both the developed synthetic protocols with good to excellent yield of the targeted molecules. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.086

文献信息

• Synthesis of 3,4-dihydropyridin-2-one derivatives in convergent mode applying bio catalyst vitamin B1 and polymer supported catalyst PEG–SO3H from two different sets of building blocks
  作者：Koyel Pradhan、Pranabes Bhattacharyya、Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.08.030

  日期：2012.10

  Two highly efficient, green protocols have been developed for the synthesis of 3,4-dihydropyridin-2-one derivatives from different starting materials exploring two reaction specific catalysts, vitamin B1 (VB1), and PEG–SO3H. VB1 catalyzed simple and convenient protocol has been developed for the synthesis of 3,4-dihydropyridin-2-one derivatives by the installation of aldehyde, cyanoacetamide, and 1

  两个高效，绿色协议已经开发了用于3,4-二氢吡啶-2-酮从不同的原料衍生物的探索两个反应特定的催化剂，维生素B合成1（VB 1）和PEG-SO 3 H. VB 1通过安装醛，氰基乙酰胺和1,3-二羰基化合物，已开发出催化简单方便的方案，用于合成3,4-二氢吡啶-2-酮衍生物。此外，通过形成4 H-吡喃核和PEG-SO 3 H催化的一锅法，将醛，丙二腈和1,3-二羰基化合物简单地结合起来，也合成了3,4-二氢吡啶-2-酮衍生物。重排。
• KRAUZE, A. A.;LIEPINSH, EH. EH.;KALME, Z. A.;PELCHER, YU. EH.;DUBUR, G. Y+, XIMIYA GETEROTSIKL. SOEDIN., 1984, N 11, 1504-1508
  作者：KRAUZE, A. A.、LIEPINSH, EH. EH.、KALME, Z. A.、PELCHER, YU. EH.、DUBUR, G. Y+

  DOI：——

  日期：——
• Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media
  作者：Pranabes Bhattacharyya、Koyel Pradhan、Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.06.086

  日期：2012.8

  A green and highly efficient protocol has been developed for the synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and a 1,3-diketo compound using nano structured ZnO as the catalyst in aqueous alcoholic medium. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran derivatives in aqueous medium applying p-TSOH as the right catalyst source. A wide spectrum of functional groups was tolerated in both the developed synthetic protocols with good to excellent yield of the targeted molecules. (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis, ex vivo and in silico studies of 3-cyano-2-pyridone derivatives with vasorelaxant activity
  作者：Fernando Hernández、Arturo Sánchez、Priscila Rendón-Vallejo、César Millán-Pacheco、Yolanda Alcaraz、Francisco Delgado、Miguel A. Vázquez、Samuel Estrada-Soto

  DOI：10.1016/j.ejmech.2013.10.018

  日期：2013.12

  and simple synthesis of 3-cyano-2-pyridone derivatives (6a–f) through 3,4-dihydropyridin-2-one oxidation process is described. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran (4a–f) derivatives in aqueous medium applying H2SO4 as the catalyst source and microwave irradiation. The vasorelaxant activity of 3-cyano-2-pyridone derivatives (6a–f) was

  描述了通过3,4-二氢吡啶-2--2-氧化方法有效而简单地合成3-氰基-2-吡啶酮衍生物（6a – f）。通过以H 2 SO 4为催化剂源和微波辐射在水介质中重排4 H-吡喃（4a - f）衍生物，还开发了一种更环保的3,4-二氢吡啶-2-酮合成方法。3-氰基-2-吡啶酮衍生物（6a – f）在去甲肾上腺素（0.1μM）预收缩的分离的胸主动脉大鼠环上有或没有内皮（分别为+ E和-E）证明。所有化合物均表现出显着的浓度依赖性和内皮依赖性血管舒张作用，其中硝基衍生物（6a和f）和化合物6d最有效，EC 50分别为7、4.4和5μM。最后，将先前描述的人L型钙通道（LCC）中心孔的3D模型修改为与亚基α-1F亚型1的NCBI序列NP_005174.2一致，将其用于对接大多数活性化合物。6a，d和f发现最低的亲和能结构停靠在由IS6，IS5，IP和IIS6螺旋线相符的同一个空腔中。在由IIS6，I