methyl 1,4,5,6-tetrahydro-2-methyl-4-(2-nitrophenyl)-6-oxo-pyridine-3-carboxylate | 130734-39-3

• 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: methyl 1,4,5,6-tetrahydro-2-methyl-4-(2-nitrophenyl)-6-oxo-pyridine-3-carboxylate
• 英文别名: methyl 1,4,5,6-tetrahydro-2-methyl-4-(2-nitrophenyl)-6-oxopyridine-3-carboxylate；Methyl-1,4,5,6-tetrahydro-2-methyl-4-(2-nitrophenyl)-6-oxo-pyridin-3-carboxylat；4-(2-nitrophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridin-2(1H)-one；6-methyl-5-methoxycarbonyl-4-(2-nitrophenyl)-3,4-dihydropyridone；1,4,5,6-tetrahydro-2-methyl-4-(2-nitro-phenyl)-6-oxo-pyridine-3-carboxylic acid methyl ester；Methyl 2-methyl-4-(2-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate；methyl 6-methyl-4-(2-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 130734-39-3
• 化学式: C₁₄H₁₄N₂O₅
• 分子量: 290.276
• InChiKey: DUGMRWWBMORGRS-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C
• 沸点：
  494.3±45.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1,4,5,6-tetrahydro-2-methyl-4-(2-nitrophenyl)-6-oxo-pyridine-3-carboxylate 在 N,N-二甲基甲酰胺 、 三氯氧磷 、 水 、 sodium acetate 作用下， 反应 0.58h， 以69%的产率得到methyl 6-chloro-5-formyl-2-methyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Eco-Friendly Methodology to Prepare N-Heterocycles Related to Dihydropyridines: Microwave-Assisted Synthesis of Alkyl 4-Arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate and 4-Arylsubstituted-4,7-dihydrofuro[3,4-b]pyridine-2,5(1H,3H)-dione

  摘要：

  本文描述了通过微波加速反应，高效合成烷基4-芳基取代-6-氯-5-甲酰基-2-甲基-1,4-二氢吡啶-3-羧酸酯和4-芳基取代-4,7-二氢-呋喃[3,4-b]吡啶-2,5(1H,3H)-二酮的方法。该环保合成途径不涉及传统加热中的苛刻或高度污染条件，减少了溶剂使用和回收，简化了后处理步骤，易于规模放大，能耗低，并且产率适中至较高。

  DOI：

  10.3390/molecules16119620
• 作为产物：
  描述：

  甲醇 、 5-(2-nitrobenzylidene)-2,2-dimethyl-1,3-dioxan-4,6-dione 、 1,3-dioxin-4-one 生成 methyl 1,4,5,6-tetrahydro-2-methyl-4-(2-nitrophenyl)-6-oxo-pyridine-3-carboxylate
  参考文献：
  名称：

  4-芳基取代的5-羧基-6-甲基-3,4-二氢吡啶酮的固相合成

  摘要：

  通过固相合成，使用Wang树脂从固定的β-酮酸酯中进行了固相合成，并进一步进行了Hantzsch型杂环化反应，从而有效地制备了3,4-二氢-2-吡啶酮。

  DOI：

  10.1016/s0040-4039(01)02172-4

文献信息

• Efficient sonochemical synthesis of alkyl 4-aryl-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate derivatives
  作者：Enrique Ruiz、Hortensia Rodríguez、Julieta Coro、Vladimir Niebla、Alfredo Rodríguez、Roberto Martínez-Alvarez、Hector Novoa de Armas、Margarita Suárez、Nazario Martín

  DOI：10.1016/j.ultsonch.2011.07.003

  日期：2012.3

  facile, efficient and environment-friendly protocol for the synthesis of 6-chloro-5-formyl-1,4-dihydropyridine derivatives has been developed by the convenient ultrasound-mediated reaction of 2(1H)pyridone derivatives with the Vilsmeier-Haack reagent. This method provides several advantages over current reaction methodologies including a simpler work-up procedure, shorter reaction times and higher yields

  通过2（1H）吡啶酮衍生物与Vilsmeier-Haack试剂的便捷超声介导反应，已开发出一种简便，高效且环境友好的合成6-氯-5-甲酰基-1,4-二氢吡啶衍生物的方案。 。与当前的反应方法相比，该方法具有多个优点，包括更简单的后处理步骤，更短的反应时间和更高的产率。
• Oxygen-bridged tetrahydropyridines, hexahydropyridines, and dihydropyridones via a Hantzsch-like synthesis with 4-(2-hydroxyphenyl)but-3-en-2-one
  作者：Jan Světlík、Igor Goljer、František Tureček

  DOI：10.1039/p19900001315

  日期：——

  Substituted oxygen-bridged tetrahydro-2-pyridones and tetrahydropyridines (4) and (7) were synthesized by condensation of 4-(2-hydroxyphenyl)but-3-en-2-one (1) with Meldrum's acid (2) and 3-aminocrotononitrile, respectively, in the presence of ammonium acetate. Analogous cyclo-condensations of (1) with methyl 3-amino-2,4-dicyanobut-2-enoate (8) and methyl 3-amino-2-cyanopentene-2-dioate (10) led to

  通过将4-（2-羟苯基）but-3-en-2-one（1）与Meldrum's酸（2）和3缩合合成取代的氧桥联的四氢-2-吡啶酮和四氢吡啶（4）和（7）。-氨基丁腈分别在乙酸铵的存在下。类似的（环缩合1）与3-氨基-2,4- dicyanobut -2-烯酸乙酯（8）和甲基3-氨基-2- cyanopentene -2-二酸盐（10导致氧桥hexahydropyridines）（9）和（11）分别在哌啶环中具有不同的立体化学。讨论了这些氧桥联杂环的立体定向途径中的二分法。还报道了4-芳基取代的二氢-2-吡啶酮的制备。
• Novel hexahydrofuro[3,4-<i>b</i>]-2(1<i>H</i>)-pyridones from 4-aryl substituted 5-alkoxycarbonyl-6-methyl-3,4-dihydropyridones
  作者：Alhmed Morales、Estael Ochoa、Margarita Suárez、Yamila Verdecia、Leandro González、Nazario Martín、Margarita Quinteiro、Carlos Seoane、José L. Soto

  DOI：10.1002/jhet.5570330118

  日期：1996.1

  The title compounds 6 have been prepared in a one-step procedure from the corresponding 4-aryl substituted 5-alkoxycarbonyl-6-methyl-3,4-dihydropyridones 4 in good yields. Quantum chemical calculations reveal a non-planar molecule with a distorted dihydropyridone ring and two favoured conformations. The 13C nmr data and theoretical calculations support a strong push-pull effect on the olefinic moiety

  标题化合物6是由相应的4-芳基取代的5-烷氧基羰基-6-甲基-3，4-二氢吡啶酮4以良好的产率一步制备的。量子化学计算揭示了具有扭曲的二氢吡啶酮环和两个有利构象的非平面分子。13C nmr数据和理论计算支持对烯烃部分的强推挽效应。
• High-throughput preparation of alkyl 4-aryl substituted-2-methyl-6-thioxo-1,4,5,6-tetrahydropyridine-3-carboxylates under microwave irradiation
  作者：Hortensia Rodríguez、Julieta Coro、Anabel Lam、Esperanza Salfrán、Javier Rodríguez-Salarichs、Margarita Suárez、Fernando Albericio、Nazario Martin

  DOI：10.3998/ark.5550190.0012.909

  日期：——

  An efficient high-throughput synthesis of 4-aryl substituted 1,4,5,6-tetrahydro-2-methyl-6thioxopyridine-3-carboxylates 5a-p was developed by using Lawesson’s reagent, a very effective thionating reagent for carbonyl compounds, under conventional conditions and microwave irradiation. In order to gain a better understanding of the structure of the heterocycles obtained, theoretical calculations at the

  4-芳基取代的 1,4,5,6-四氢-2-甲基-6thioxopyridine-3-carboxylates 5a-p 的高效高通量合成是通过使用 Lawesson 试剂开发的，劳森试剂是一种非常有效的羰基化合物硫代试剂，在常规条件和微波辐射。为了更好地理解所得杂环的结构，进行了从头算水平的理论计算。
• Goerlitzer; Enge; Jones, Pharmazie, 2006, vol. 61, # 1, p. 4 - 9
  作者：Goerlitzer、Enge、Jones

  DOI：——

  日期：——