diethyl 2,6-dimethyl-4-[4-(methylsulfanyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate | 939331-82-5

• 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: diethyl 2,6-dimethyl-4-[4-(methylsulfanyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: Diethyl 2,6-dimethyl-4-(4-methylsulfanylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 939331-82-5
• 化学式: C₂₀H₂₅NO₄S
• 分子量: 375.489
• InChiKey: ZBKOAFLOCPGJSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 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：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2,6-dimethyl-4-[4-(methylsulfanyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate 在 dipotassium peroxodisulfate 作用下， 以 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  通过将乙酸乙酯从芳香环中电化学挤出，将汉茨酯及其衍生物环缩合为吡咯

  摘要：

  开发了HEs及其吡啶衍生物的电化学环收缩法以获得多取代的吡咯。该方法提供了Hantzsch酯作为侧链或氢供体在正交文献中的正交应用。正式的转化显示了一步就将乙酸乙酯从吡啶环中挤出。除了新颖的转化，我们还发现了路易斯酸在分子内电化学过程中的区域选择性的分子间控制。该反应提供了许多从未得到的多取代的吡咯，包括药物中间体和光开关。不寻常的4电子连续还原反应驱动了前所未有的阴离子脱芳香化/环收缩/再芳香化途径。

  DOI：

  10.1039/d1gc00487e
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4-(甲基巯基)苯甲醛 在 benzyltrimethylammonium fluoride 、 ammonium acetate 作用下， 反应 0.25h， 以89%的产率得到diethyl 2,6-dimethyl-4-[4-(methylsulfanyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  苄基三甲基氟化铵水合物：一锅法合成 Hantzsch 1,4-二氢吡啶及其芳构化的高效催化剂

  摘要：

  已开发出一种高效、经济且简单的方案，用于在无溶剂条件下使用苄基三甲基氟化铵水合物作为优异催化剂合成 Hantzsch 1,4-二氢吡啶并将其氧化成吡啶。通过该方法合成的所有产品均通过各种光谱方法（IR、1H NMR、13C NMR 和 DEPT）进行表征。

  DOI：

  10.1002/hc.21308

文献信息

• <scp>l</scp>-Tyrosine loaded nanoparticles: an efficient catalyst for the synthesis of dicoumarols and Hantzsch 1,4-dihydropyridines
  作者：Anamika Khaskel、Pranjit Barman、Utpal Jana

  DOI：10.1039/c4ra16627b

  日期：——

  l-Tyrosine loaded nanoparticles catalyzed organic reactions.

  -酪氨酸载荷的纳米颗粒催化有机反应。
• One-Pot and Solvent-Free Synthesis of 1,4-Dihydropyridines and 3,4-Dihydropyrimidine-2-ones Using New Synthetic Recyclable Catalyst via Biginelli and Hantzsch Reactions
  作者：Abbas Shockravi、Mahmood Kamali、Negar Sharifi、Mahdieh Nategholeslam、Somayeh Pahlavan Moghanlo

  DOI：10.1080/00397911.2011.642923

  日期：2013.6.3

  Pyridine dicarboxylic acid guanidine-cobalt complex (PDAG-Co) (3) catalyzes one-pot, three-component coupling of aldehydes, -dicarbonyl compounds, and ammonium acetate to afford the corresponding 1,4-dihydropyridines (1,4-DHPs) via Hantzsch reaction. 3,4-Dihydropyrimidine-2-ones (3,4-DHPMs) and their sulfur analogs are also synthesized under the same conditions via Biginelli condensation protocol. The catalyst is reusable at least five times, highly efficient, easily prepared, and used under mild reaction conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view free supplemental file.
• Synthesis of diethyl 4-substituted-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates as a new series of inhibitors against yeast α-glucosidase
  作者：Huma Niaz、Hamdy Kashtoh、Jalaluddin A.J. Khan、Ajmal Khan、Atia-tul- Wahab、Muhammad Tanveer Alam、Khalid Mohammed Khan、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.ejmech.2015.03.018

  日期：2015.5

  1,4-Dihydropyridine-3,5-dicarboxylate derivatives (1-25) were synthesized in high yields via Hantzsch reaction and evaluated for their a-glucosidase inhibitory activity. Compounds 1, 2, 6-8, 11, 13-15, and 23-25 showed a potent inhibitory activity against yeast alpha-glucosidase with IC50 values in the range of 35.0-273.7 mu M, when compared with the standard drug acarbose (IC50 = 937 +/- 1.60 mu M). Their structures were characterized by different spectroscopic techniques. The kinetics, selectivity, and toxicity studies on these compounds were also carried out. The kinetic studies on most active compounds 14 and 25 determined their modes of inhibition and dissociation constants K-i. Compound 14 was found to be a noncompetitive inhibitor with K-i = 25.0 +/- 0.06, while compound 25 was identified as a competitive inhibitor with K-i = 66.0 +/- 0.07 mu M. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Ring-contraction of hantzsch esters and their derivatives to pyrroles <i>via</i> electrochemical extrusion of ethyl acetate out of aromatic rings
  作者：Xu Liu、Chang Liu、Xu Cheng

  DOI：10.1039/d1gc00487e

  日期：——

  ring-contraction of HEs and theirs pyridine derivatives is developed to obtain polysubstituted pyrroles. This process provides an orthogonal utilization of Hantzsch esters for the well-documented application as side chain or hydrogen donors. The formal transformation shows an extrusion of ethyl acetate out of the pyridine ring in a single step. In addition to the novel transformation, we also discovered the Lewis

  开发了HEs及其吡啶衍生物的电化学环收缩法以获得多取代的吡咯。该方法提供了Hantzsch酯作为侧链或氢供体在正交文献中的正交应用。正式的转化显示了一步就将乙酸乙酯从吡啶环中挤出。除了新颖的转化，我们还发现了路易斯酸在分子内电化学过程中的区域选择性的分子间控制。该反应提供了许多从未得到的多取代的吡咯，包括药物中间体和光开关。不寻常的4电子连续还原反应驱动了前所未有的阴离子脱芳香化/环收缩/再芳香化途径。
• Benzyltrimethylammoniumfluoride Hydrate: An Efficient Catalyst for One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines and Their Aromatization
  作者：Anamika Khaskel、Pranjit Barman

  DOI：10.1002/hc.21308

  日期：2016.3

  An efficient, cost-effective and simple protocol has been developed for the synthesis of Hantzsch 1,4-dihydropyridines and their oxidation into pyridines using benzyltrimethylammonium fluoride hydrate as an excellent catalyst under solvent-free condition. All of the products synthesized by this method are characterized by various spectroscopic methods (IR, 1H NMR, 13C NMR, and DEPT).

  已开发出一种高效、经济且简单的方案，用于在无溶剂条件下使用苄基三甲基氟化铵水合物作为优异催化剂合成 Hantzsch 1,4-二氢吡啶并将其氧化成吡啶。通过该方法合成的所有产品均通过各种光谱方法（IR、1H NMR、13C NMR 和 DEPT）进行表征。