Methyl 6-chloro-4-(2-chlorophenyl)-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate | 177763-76-7

• 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: Methyl 6-chloro-4-(2-chlorophenyl)-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate
• CAS: 177763-76-7
• 化学式: C₁₅H₁₃Cl₂NO₃
• 分子量: 326.179
• InChiKey: PTHFXYVCLLUZEN-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  431.7±45.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 6-chloro-4-(2-chlorophenyl)-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-(2-chlorophenyl)-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：

  N,N-二甲基甲酰胺 、 4-(2-chlorophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridin-2(1H)-one 在 三氯氧磷 、 水 、 sodium acetate 作用下， 以 氯仿 为溶剂， 反应 0.42h， 以92%的产率得到Methyl 6-chloro-4-(2-chlorophenyl)-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  4-芳基-6-氯-5-甲酰基-2-甲基-1,4-二氢吡啶-3-羧酸烷基酯衍生物的高效声化学合成。

  摘要：

  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。

  DOI：

  10.1016/j.ultsonch.2011.07.003

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.
• Synthesis and Structural Study of Semicarbazone-Containing 1,4-Dihydropyridine
  作者：Nazario Martín、Yamila Verdecia、Estael Ochoa、Blavet Barried、Dolores Molero、Carlos Seoane、Hector Novoa、Norbert M. Blaton、Oswald M. Peetersd、Amaury Álvarez、Margarita Suárez、Rolando Pérez、Mercedes Díaz、Roberto Martínez-Álvarez

  DOI：10.3987/com-06-10776

  日期：——
• Synthesis and study of novel fulleropyrrolidines bearing biologically active 1,4-dihydropyridines
  作者：Margarita Suárez、Yamila Verdecia、Beatriz Illescas、Roberto Martı́nez-Alvarez、Amaury Alvarez、Estael Ochoa、Carlos Seoane、Nour Kayali、Nazario Martı́n

  DOI：10.1016/j.tet.2003.09.047

  日期：2003.11

  New fulleropyrrolidines endowed with chlorine-containing biological active 1,4-dihydropyridines (1,4-DHPs) have been synthesised from the respective formyl substituted 1,4-DHPs by following Prato's procedure. The presence of the chlorine atom on C2 of the 1,4-DHP ring brings about important spectroscopical and structural differences in compounds 10a-f related to the parent hydrogen-containing 11a. The mass spectroscopy study reveals different fragmentation patterns for fulleropyrrolidines 10a-f and their precursors 1,4-DHPs, as well as with 11a. Semiempirical calculations (AMI and PM3) predict a most stable stereoisomer in all cases (RS for 10a-f) and the same RR for 11a. The presence of chlorine atom in 10a-f is responsible for the higher calculated conformational energy barriers in comparison with 11a. The geometry of:the 1,4-DHP shows that the presence of fullerene unit does not significantly alter the required conformation for biological activity. (C) 2003 Elsevier Ltd. All rights reserved.
• ——
  作者：Héctor Novoa de Armas、Norbert M. Blaton、Oswald M. Peeters、Camiel J. De Ranter、Margarita Suárez、Estael Ochoa、Yamila Verdecia、Esperanza Salfrán

  DOI：10.1023/a:1009539005669

  日期：——

  The synthesis and structural characterization of Methyl 6-chloro-4-(2-chlorophenyl)-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate is described. The structure was refined to R-1 = 0.0470 for 2665 reflections (with I > 2 sigma (I)). Crystal data: C15H13C12NO3, monoclinic, space group P2(1)/c, a = 11.163(9), b = 14.484(8), c = 9.422(7) Angstrom, V = 1512.9(19) Angstrom (3), Z = 4. The results of crystallographic and molecular modeling (AM1) were compared. The Cl atom attached to the phenyl group has two possible orientations, having 75% (sp) and 25% (ap) occupancy, respectively. The molecules in the crystal are held together by means of intermolecular hydrogen bonds of the type N-H . . .O and by C-H . . .O interactions.