methyl 6-chloro-4-(4'-methoxycarbonylphenyl)-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate | 177763-79-0

• 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 6-chloro-4-(4'-methoxycarbonylphenyl)-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate
• 英文别名: Methyl 6-chloro-5-formyl-4-(4-methoxycarbonylphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
• CAS: 177763-79-0
• 化学式: C₁₇H₁₆ClNO₅
• 分子量: 349.771
• InChiKey: LRBXFZANZCYMQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-chloro-4-(4'-methoxycarbonylphenyl)-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以60%的产率得到Methyl 4-(4-methoxycarbonylphenyl)-6-methyl-4,7-dihydro-1H-pyrazolo<3,4-b>pyridine-5-carboxylate
  参考文献：
  名称：

  Synthesis of methyl 4-aryl-6-methyl-4,7-dihydro-1H-pyrazolo-[3,4-b]pyridine-5-carboxylates from methyl 4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates

  摘要：

  Novel methyl 4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5 3a-e have been prepared in a two step procedure from the readily available 2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates 1a-e by treatment with the Vilsmeier-Haack reagent. Further treatment of the novel o-chloroformyl substituted methyl 1,4-dihydropyridine-5-carboxylates 2a-e with hydrazine affords the corresponding methyl pyrazolo[3,4-b]pyridine-5-carboxylates in good yields. Semiempirical calculations reveal a favoured geometry with a boat conformation in the dihydropyridine system and a planar pyrazole ring.

  DOI：

  10.1039/p19960000947
• 作为产物：
  描述：

  Methyl 4-(4-methoxycarbonylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-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63%的产率得到methyl 6-chloro-4-(4'-methoxycarbonylphenyl)-5-formyl-2-methyl-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

文献信息

• Synthesis and structural characterization of substituted thieno[2,3-<i>b</i>]pyridines from<i>o</i>-chloroformyl-1,4-dihydropyridines
  作者：Margarita Suárez、Estael Ochoa、Beatriz Pita、Remberto Espinosa、Leandro González、Nazario Martín、Margarita Quinteiro、Carlos Seoane、Jose L. Soto

  DOI：10.1002/jhet.5570340334

  日期：1997.5

  9a-d and ethyl mercaptoacetate in good yields. Semiempirical calculations reveal a favoured geometry with a boat conformation in the dihydropyridine system and a planar thieno ring. The calculated charge density values for the olefmic carbons (C5 and C6) are in agreement with the experimental push-pull effect observed in the 13C nmr.

  一种新的4，7-二氢噻吩并[2，3- b ]吡啶10a-d以一步法由容易获得的邻氯甲酰基取代的1，4-二氢吡啶9a-d和巯基乙酸乙酯制成。半经验计算显示了在二氢吡啶体系中具有舟状构型和平面噻吩环的良好几何形状。分子碳（C5和C6）的计算电荷密度值与在13 C nmr中观察到的实验推挽效应一致。
• A straightforward synthesis and structure of unprecedented iminium salts of dihydropyrido[3,2-e][1,3]thiazines
  作者：Margarita Suárez、Hector Novoa、Yamila Verdecia、Estael Ochoa、Amaury Alvarez、Rolando Pérez、Roberto Martínez-Alvarez、Dolores Molero、Carlos Seoane、Norbert M. Blaton、Oswald M. Peeters、Nazario Martín

  DOI：10.1016/j.tet.2005.11.054

  日期：2006.2

  Unprecedented 2-iminium chloride salts of 5,8-dihydro-2H-pyrido[3,2-e][1,3]thiazines derivatives (8) were easily synthesized in one step from the corresponding o-chloroformyl-1,4-dihydropyridime (2) and thiourea. The Structural Study has been carried out by X-ray crystallography and theoretical calculations at the B3LYP/6-31G* levels and reveal that the new salts exhibit appropriate structural features to behave as calcium channel modulators. (c) 2005 Elsevier Ltd. All rights reserved.