3,5-diacetyl-2,6-dimethyl-4-(4'-hydroxyphenyl)-1,4-dihydropyridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-diacetyl-2,6-dimethyl-4-(4'-hydroxyphenyl)-1,4-dihydropyridine
• 英文别名: 1-[5-acetyl-4-(4-hydroxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridin-3-yl]-ethanone；1-[5-Acetyl-4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridin-3-yl]ethanone
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: XZPOIGBEFVDMEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对羟基苯甲醛 、 乙酰丙酮 在 1%Cu/ZnO 、 ammonium acetate 作用下， 以 水 为溶剂， 反应 1.75h， 以92%的产率得到3,5-diacetyl-2,6-dimethyl-4-(4'-hydroxyphenyl)-1,4-dihydropyridine
  参考文献：
  名称：

  Cu-doped ZnO nanocrystalline powder as a catalyst for green and convenient multi-component synthesis of 1,4-dihydropyridine

  摘要：

  报道了一种简单、高效、方便的一步法合成Hantzsch 1,4-二氢吡啶，采用掺铜ZnO纳米结晶粉末作为催化剂。该方法具有多个优点，包括优异的产率、绿色溶剂、简单的后处理、易操作和催化剂可重复使用。

  DOI：

  10.1007/s11164-014-1712-8

文献信息

• Triton-X-100 catalyzed synthesis of 1,4-dihydropyridines and their aromatization to pyridines and a new one pot synthesis of pyridines using visible light in aqueous media
  作者：Partha Pratim Ghosh、Prasun Mukherjee、Asish R. Das

  DOI：10.1039/c3ra40706c

  日期：——

  temperature. A greener method to synthesize pyridine derivatives has also been developed by the oxidation of 1,4-dihydropyridine derivatives with almost 100% yields and also in a one pot synthesis, employing an aldehyde, ethyl acetoacetate and ammonium acetate in an aqueous micellar medium by irradiation with potassium persulphate in the presence of visible light. The one pot protocol offered excellent

  已经开发出一种现实且方便的合成方法，用于在室温下在水性介质中在非离子表面活性剂Triton X-100存在下轻松合成1,4-二氢吡啶衍生物。通过以几乎100％的收率氧化1,4-二氢吡啶衍生物，并且还在通过在胶束介质中的醛，乙酰乙酸乙酯和乙酸铵进行辐射的单罐合成中，已经开发了一种更绿色的合成吡啶衍生物的方法。在可见光下用过硫酸钾。一锅操作方案可在室温下非常短的时间内提供优异的目标产物收率，而且非离子表面活性剂催化剂可以很容易地回收。我们还观察到在反应过程中形成了胶束，来自非离子表面活性剂和水中反应混合物的胶束状或胶束状胶体聚集体，通过动态光散射法测量并通过光学显微镜观察。该方法是有利的，因为在绝对中性的条件下从铵盐中产生氨，并且产物的纯化遵循组助剂纯化化学过程（GAP）。
• Solvent-free efficient one-pot synthesis of Biginelli and Hantzsch compounds catalyzed by potassium phthalimide as a green and reusable organocatalyst
  作者：Hamzeh Kiyani、Maryam Ghiasi

  DOI：10.1007/s11164-014-1621-x

  日期：2015.8

  The usage of potassium phthalimide (PPI) for the simple and green one-step multicomponent synthesis of Hantzsch 1,4-dihydropyridines, polyhydroquinolines, 3,4-dihydropyrimidin-2(1H)-ones/thiones, and octahydroquinazolinones under solventless conditions at 120 °C is reported. The method is operationally simple, environmentally benign, and has relatively high yields. The other merits of this method include efficient, clean, green, and catalyst reusability.

  本文报道了在无溶剂条件下，于120°C下使用邻苯二甲酰亚胺钾（PPI）进行Hantzsch 1,4-二氢吡啶、多氢喹啉、3,4-二氢嘧啶-2(1H)-酮/硫酮以及八氢喹唑啉酮的一步多组分简单绿色合成。该方法操作简便，环境友好，且产率相对较高。此外，该方法还具有高效、清洁、绿色以及催化剂可重复使用的优点。
• Experimental and theoretical structural study of 2-pyridyl- and 4-hydroxyphenyl-1,4-dihydropyridine derivatives
  作者：Héctor Novoa De Armas、Norbert Blaton、Oswald M. Peeters、Camiel De Ranter、Margarita Suárez、Emilio Rolando、Yamila Verdecia、Estael Ochoa、Nazario Martín、Margarita Quinteiro、Carlos Seoane、José L. Soto

  DOI：10.1002/jhet.5570370627

  日期：2000.11

  symmetrical 1,4-DHP. The structures of these compounds have been thoroughly studied by X-ray crystallographic analysis and semiempirical (AMI) calculations. A good agreement is found between the theoretical and experimental results. In all cases, the most stable conformation fulfils all the requirements needed for exhibiting an antagonist calcium effect.

  按照众所周知的对称1,4-DHP的Hantzsch程序合成了一系列取代的1,4-二氢吡啶（1,4-DHP）。这些化合物的结构已通过X射线晶体学分析和半经验（AMI）计算进行了深入研究。在理论和实验结果之间找到了很好的一致性。在所有情况下，最稳定的构象均满足显示拮抗剂钙效应所需的所有要求。
• 1,4-Dihydropyridine charge control agents for electrostatographic toners and developers
  申请人：EASTMAN KODAK COMPANY

  公开号：EP1109070A2

  公开（公告）日：2001-06-20

  A charge control agent is disclosed selected from the group consisting of 1,4-dihydropyridines having the following general structure: where R1, R2, R3, R4, R5, X, and Z are defined in the specification. These compounds are useful in electrostatographic toners and developers.

  本发明公开了一种电荷控制剂，它选自具有以下一般结构的 1,4-二氢吡啶类： 其中 R1、R2、R3、R4、R5、X 和 Z 的定义见说明书。这些化合物适用于电致发光调色剂和显影剂。
• Light induced synthesis of symmetrical and unsymmetrical dihydropyridines in ethyl lactate–water under tunable conditions
  作者：Partha Pratim Ghosh、Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.10.106

  日期：2013.1

  A highly efficient environment-friendly one-pot green methodology has been developed for the synthesis of symmetrical and unsymmetrical 1,4-dihydropyridines and polyhydroquinolines following the multicomponent Hantzsch synthesis under visible light irradiation in ethyl-L-lactate-water solution at room temperature. The present methodology offers several advantages such as simple procedure, greener condition, excellent yields and short reaction time sans any catalyst, support or promoter. The developed protocol has been materialized with the involvement of a household compact tungsten lamp as the visible light source, and the manifested high selectivity of the reaction performed in ethyl lactate-water solvent mixture under tunable conditions. The Ca2+ channel blocker nitrendipine and nemadipine B were also successfully synthesized applying the developed methodology in high yields. (C) 2012 Elsevier Ltd. All rights reserved.

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