4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester | 116324-75-5

• 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: 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 1,4-dihydro-4-(3-hydroxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate；dimethyl-4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate；Dimethyl 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 116324-75-5
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: HWTUTDXHWQLDFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester 在 graphite oxide 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以92%的产率得到dimethyl 4-(3-hydroxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Graphite oxide mediated oxidative aromatization of 1,4-dihydropyridines into pyridine derivatives

  摘要：

  A new approach utilizing graphite oxide as an oxidizing agent is applied for the oxidative aromatization of 1,4-dihydropyridines. Graphite oxide efficiently aromatized Hantzsch 1,4-dihydropyridines into their corresponding pyridine derivatives in excellent yields. The reaction was carried out in toluene at 100 degrees C. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.026
• 作为产物：
  描述：

  3-烯丙氧基-苯甲醛 在 四氯化钛 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Sar, Cecilia P.; Hankovszky, Olga H.; Jerkovich, Gy., ACH - Models in Chemistry, 1994, vol. 131, # 3-4, p. 363 - 376

  摘要：

  DOI：

文献信息

• [Fesipmim]Cl as highly efficient and reusable catalyst for solventless synthesis of dihydropyridine derivatives through Hantzsch reaction
  作者：Akansha Agrwal、Virendra Kasana

  DOI：10.1007/s12039-020-01770-9

  日期：2020.12

  catalyst were measured by vibrating sample magnetometer (VSM). The efficiency of the [Fesipmim]Cl catalyst was checked by using it for the synthesis of different derivatives of dihydropyridine through Hantzsch reaction via a three-component coupling reaction of substituted benzaldehydes, ethyl/ methyl acetoacetate and ammonium acetate. The formation and structures of all the synthesized compounds were confirmed

  摘要 在本研究中，合成了磁性铁氧体纳米粒子（铁氧体NPs）并通过溶胶-凝胶法用二氧化硅（ferrite @ SiO 2 NPs）进行了包覆。然后，制备二氧化硅丙基甲基咪唑氯化物离子液体[Sipmim] Cl，并与上述制备的铁氧体@SiO 2 NPs连接，以合成铁氧体二氧化硅丙基甲基咪唑氯化物[Fesipmim] Cl催化剂。[Fesipmim] Cl催化剂的形成通过傅立叶变换红外（FT-IR）光谱分析确认。X射线衍射（XRD）分析证实了铁氧体NPs和铁氧体@SiO 2 NPs的结构。透射电子显微镜（TEM）证明成功形成了铁素体NP和铁素体@SiO 2NP。扫描电子显微镜（SEM）结果表明，铁氧体NPs，铁素体@SiO 2 NPs和[Fesipmim] Cl的形态发生了变化。通过振动样品磁力计（VSM）测量[Fesipmim] Cl催化剂的磁性。[Fesipmim] Cl催化剂的效率通过使用
• Synthesis of hantzsch 1,4-dihydropyridines under solvent-free condition using zn[(L)proline]₂as lewis acid catalyst
  作者：V. Sivamurugan、R. Suresh Kumar、M. Palanichamy、V. Murugesan

  DOI：10.1002/jhet.5570420534

  日期：2005.7

  The present short communication describes a Lewis acid (Zn[(L)proline]2) catalysed one pot synthesis of Hantzsch 1,4-dihydropyridine (DHP) derivatives under solvent-free condition by conventional heating and microwave irradiation. The Lewis acid catalyst Zn[(L)proline]2 used in this reaction afford moderate to good yield. The catalyst is reusable upto five cycles without appreciable loss of its catalytic

  本简短的交流描述了路易斯酸（Zn [（L）脯氨酸] 2）在无溶剂条件下通过常规加热和微波辐射催化一锅合成Hantzsch 1,4-二氢吡啶（DHP）衍生物。在该反应中使用的路易斯酸催化剂Zn [（L）脯氨酸] 2提供中等至良好的产率。该催化剂可重复使用多达五个循环，而不会明显丧失其催化活性。
• Synthesis and Antimicrobial Evaluation of 2-Aminobenzophenone Linked 1,4-Dihydropyridine Derivatives
  作者：Pengying Li、Ketki Sahore、Jianjun Liu、Rajesh K. Singh

  DOI：10.14233/ajchem.2014.17403

  日期：——

  A series of novel aminobenzophenone linked 1,4-dihydropyridines (1,4-DHPs) hybrids were synthesized by incorporating aminobenzophenone moiety on 1,4-dihydropyridines scaffold (5a-f) and characterized by IR, 1H NMR and CHN elemental analysis. The synthesized compounds were tested for their in vitro antibacterial activity against the Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Among all the synthesized compounds, compounds 5b, 5c and 5e have shown the maximum activity in their group whereas compounds 5a, 5d, 5f have shown the minimum activity.

  一系列新型氨基苯基酮连接的1,4-二氢吡啶（1,4-DHPs）杂合物通过在1,4-二氢吡啶骨架（5a-f）上引入氨基苯基酮部分合成而成，并通过红外光谱、氢谱（1H NMR）及CHN元素分析进行了表征。合成的化合物在体外测试了其对阳性菌（葡萄球菌）和阴性菌（大肠杆菌）的抗菌活性。在所有合成的化合物中，化合物5b、5c和5e显示出该组中的最大活性，而化合物5a、5d和5f则表现出最小活性。
• Jain; Narang; Jindal, Pharmazie, 2006, vol. 61, # 5, p. 400 - 405
  作者：Jain、Narang、Jindal、Bansal, Ranju、Calle、Carron、Pemberton、Harvey

  DOI：——

  日期：——
• Hybrid pharmacophore-based drug design, synthesis, and antiproliferative activity of 1,4-dihydropyridines-linked alkylating anticancer agents
  作者：Rajesh K. Singh、D. N. Prasad、T. R. Bhardwaj

  DOI：10.1007/s00044-014-1236-1

  日期：2015.4

  Two series of novel substituted 1,4-dihydropyridine derivatives incorporating nitrogen mustard pharmacophore hybrids without spacer DHP-M (4a-4d) and with ethyl spacer DHP-L-M (8a-8g) were designed and synthesized. They were subjected to in silico ADME prediction study to check their drug-like properties and evaluated for their cytotoxicity against: A 549 (lung), COLO 205 (colon), U 87 (glioblastoma), and IMR-32 (neuroblastoma) human cancer cell lines in vitro using 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay against chlorambucil and docetaxel. Majority of the test compounds exhibited moderate to significant cytotoxic activity. The highest activity in all the investigated cancer cells was displayed by DHP-M (4a). This may be due to the less steric hindrance offered by 4a.