2,6-dimethyl-3,5-di(ethoxycarbonyl)-4-(3-hydroxy-4-methoxyphenyl)-1,4-dihydropyridine | 320741-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-dimethyl-3,5-di(ethoxycarbonyl)-4-(3-hydroxy-4-methoxyphenyl)-1,4-dihydropyridine
• 英文别名: Diethyl 4-(3-hydroxy-4-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 320741-61-5
• 化学式: C₂₀H₂₅NO₆
• mdl: MFCD00717485
• 分子量: 375.422
• InChiKey: CBKXUHBWDZNIAE-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168 °C
• 沸点：
  515.5±50.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-3,5-di(ethoxycarbonyl)-4-(3-hydroxy-4-methoxyphenyl)-1,4-dihydropyridine 在 盐酸 、 sodium chlorite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以99%的产率得到diethyl 2,6-dimethyl-4-(3-hydroxy-4-methoxyphenyl)pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  亚氯酸钠对Hantzsch 1,4-二氢吡啶的氧化芳构化作用

  摘要：

  在温和的条件下，亚氯酸钠可有效地将Hantzsch 1,4-二氢吡啶有效转化为相应的吡啶，并具有优异的收率。

  DOI：

  10.1016/j.tetlet.2010.05.091
• 作为产物：
  描述：

  异香兰素 、 3-氨基巴豆酸乙酯 在 溶剂黄146 作用下， 反应 1.0h， 以62%的产率得到2,6-dimethyl-3,5-di(ethoxycarbonyl)-4-(3-hydroxy-4-methoxyphenyl)-1,4-dihydropyridine
  参考文献：
  名称：

  Synthesis of Some C‐3,4,5‐Substituted 2,6‐Dimethyl‐1,4‐dihydropyridines (4‐DHPs)

  摘要：

  DOI：

  10.1080/00397910701357007

文献信息

• Anchored sulfonic acid on silica-layered NiFe2O4: A magnetically reusable nanocatalyst for Hantzsch synthesis of 1,4-dihydropyridines
  作者：Behzad Zeynizadeh、Soleiman Rahmani、Elham Eghbali

  DOI：10.1016/j.poly.2019.04.035

  日期：2019.8

  Abstract In this study, the immobilization of sulfonic acid on silica-layered nickel ferrite, NiFe2O4@SiO2@SO3H, was investigated. The sulfonated Ni-nanocatalyst was then characterized using FT-IR, SEM, EDX, XRD and VSM analyses. Catalytic activity of the Ni-nanocomposite was also studied towards Hantzsch synthesis of 1,4-dihydropyridines via one-pot condensation reaction of 1,3-diketones (ethyl acetoacetate

  摘要研究了磺酸固定在二氧化硅层状镍铁氧体NiFe2O4 @ SiO2 @ SO3H上的方法。然后使用FT-IR，SEM，EDX，XRD和VSM分析对磺化的镍纳米催化剂进行表征。还研究了Ni-纳米复合物对1,3-二酮（乙酰乙酸乙酯或4-羟基香豆素），芳族醛和氨水在H2O中的一锅缩合反应对Hantzsch合成1,4-二氢吡啶的催化活性。 C）作为绿色溶剂。所有反应都在10-100分钟内进行，以高到极好的收率得到产物。通过检查NiFe2O4 @ SiO2 @ SO3H MNPs连续七个循环的可重复使用性，而没有明显降低催化活性，对该合成规程的绿色方面进行了更多研究。
• 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。
• <scp>One‐pot</scp> synthesis of 1, <scp>4‐dihydropyridine</scp> derivatives using the <scp> Fe ₂ ZnAl ₂ O ₇ </scp> catalyzed Hantzsch <scp>three‐component</scp> reaction
  作者：Reza Zargarzadeh、Karim Akbari Dilmaghani、Abbas Nikoo

  DOI：10.1002/jccs.202000322

  日期：2021.7

  effective one-pot method was developed for the synthesis of 1,4-dihydropyridine derivatives with high yields through the three-component reaction of ammonium acetate, ethyl acetoacetate, and aromatic aldehydes using Fe2ZnAl2O7 as catalyst. The reaction was conducted at 70–80°C temperature under solvent free conditions. The developed method had some great advantages, including safe and clean reaction conditions

  使用Fe 2 ZnAl 2 O，通过乙酸铵、乙酰乙酸乙酯和芳香醛的三组分反应，开发了一种简便、低成本、高效的一锅法合成1,4-二氢吡啶衍生物7作为催化剂。反应在 70-80°C 温度下在无溶剂条件下进行。该方法具有反应条件安全清洁、产品收率高、反应时间短、新型高效多相催化剂等优点。所开发的多相固体催化剂在一锅多组分合成中具有高效率和可重复使用性，因此可以轻松重复使用四到五次，而不会显着降低效率和产品收率。该催化剂通过扫描电子显微镜（SEM）/能量色散X射线光谱（EDS）和X射线衍射技术进行表征。制备的纳米复合材料的 N2 吸附等温线显示表面积为 2.1313E+01 m 2 /g，总孔体积为 3.0957E-02 cm 3/G。取代的二氢吡啶衍生物使用1 H NMR 和13 C NMR 以及元素光谱数据进行表征和确认。
• Aromatization of 1,4-dihydropyridines with selenium dioxide
  作者：Xiao-hua Cai、Hai-jun Yang、Guo-lin Zhang

  DOI：10.1139/v05-058

  日期：2005.3.1

  1,4-Dihydropyridines were aromatized to corresponding pyridines using stoichiometric selenium dioxide at ambient temperature in a yield of 87%~98%.Key words: 1,4-dihydropyridines, aromatization, oxidation, pyridine derivatives, selenium dioxide.

  1,4-二氢吡啶在常温下用化学计量的二氧化硒芳构化为相应的吡啶，产率为87%~98%。关键词：1,4-二氢吡啶，芳构化，氧化，吡啶衍生物，二氧化硒。
• 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.