1-[5-乙酰基-2,6-二甲基-4-(2-硝基苯基)-1,4-二氢吡啶-3-基]乙酮 | 34551-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[5-乙酰基-2,6-二甲基-4-(2-硝基苯基)-1,4-二氢吡啶-3-基]乙酮
• 英文名称: (2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-diyl)diethanone
• 英文别名: 3,5-Diacetyl-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridin；4-(2-Nitrophenyl)-2,6-dimethyl-3,5-diacetyl-1,4-dihydropyridine；1-[5-acetyl-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridin-3-yl]ethanone
• CAS: 34551-63-8
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: AJUAJYUOPRGZPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 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：
  92
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[5-乙酰基-2,6-二甲基-4-(2-硝基苯基)-1,4-二氢吡啶-3-基]乙酮 在 乙醇 作用下， 生成 3,5-Diacetyl-2,6-dimethyl-4-(2-nitrosophenyl)-pyridin
  参考文献：
  名称：

  Studies on Dihydropyridines. I. The Preparation of Unsymmetrical 4-Aryl-1,4-dihydropyridines by the Hantzsch-Beyer Synthesis¹

  摘要：

  DOI：

  10.1021/ja01607a066
• 作为产物：
  描述：

  邻硝基苯甲醛 生成 1-[5-乙酰基-2,6-二甲基-4-(2-硝基苯基)-1,4-二氢吡啶-3-基]乙酮
  参考文献：
  名称：

  1.杂环化合物的新合成。第十三部分。一些10-氨基-1：3-二甲基-2：9-二氮杂菲

  摘要：

  DOI：

  10.1039/jr9520000001

文献信息

• Ionic Liquid [EMIM]OAc under Ultrasonic Irradiation towards Synthesis of 1,4-DHP's
  作者：B. Palakshi Reddy、K. Rajesh、V. Vijayakumar

  DOI：10.1002/jccs.201190041

  日期：2011.6

  The ionic liquid 1‐ethyl‐3‐methylimidazole acetate ([EMIM]OAc) was found to be a mild and effective catalyst for the efficient, one‐pot, three‐component synthesis of 1,4‐dihydropyridines from arylaldehydes, ethylacetoacetate/acetylacetone and ammonium acetate at room temperature under sonication. The developed method has many advantages, including devoid of harmful catalysts, reacting at room temperature

  发现离子液体1-乙基-3-甲基咪唑乙酸酯（[EMIM] OAc）是一种温和而有效的催化剂，可从芳基醛，乙酰乙酸乙酯/乙酰丙酮高效，一锅，三组分合成1,4-二氢吡啶和乙酸铵在室温下超声处理。所开发的方法具有许多优点，包括没有有害的催化剂，在室温下反应，以简单的方法或操作方便的更高产率。
• 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。
• Ultrasound-mediated, uranyl nitrate hexahydrate-catalyzed synthesis of 1,4-dihydropyridines under mild conditions
  作者：B. Palakshi Reddy、S. Sarveswari、V. Vijayakumar

  DOI：10.1007/s11164-014-1784-5

  日期：2015.9

  Synthesis of 1,4-dihydropyridines by three-component condensation reaction of aldehyde, 1,3-dicarbonyl compounds, and ammonium acetate have been found to be efficiently catalyzed by uranyl nitrate hexahydrate [UO2(NO3)2 · 6H2O] at room temperature under ultrasound irradiation. This novel synthetic method offers the advantages of high yields, short reaction times, simplicity, and easy workup compared

  通过醛，1,3-二羰基化合物和乙酸铵的三组分缩合反应合成1,4-二氢吡啶被发现可被六水合硝酸铀酰[UO 2（NO 3）2 · 6H 2 O]有效地催化。在室温下超声照射下。与文献中报道的常规方法相比，这种新颖的合成方法具有高收率，反应时间短，简单且易于后处理的优点。
• 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。
• Electron Transfer-induced Aromatization of 1,4-Dihydropyridines
  作者：Hamid R. Memarian、Marieh Ghazaie、Somayeh Kakhki Mehneh

  DOI：10.1515/znb-2009-1012

  日期：2009.10.1

  A wide variety of 3,5-dicarboethoxy-1,4-dihydropyridines and 3,5-diacetyl-1,4-dihydropyridines are aromatized to the pyridine derivatives by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at room temperature and under microwave irradiation. An electron transfer-induced mechanism is proposed for this reaction which is influenced by the nature of the solvent, the nature of the substituents located on 3-, 4- and 5-positions of the 1,4-dihydropyridine ring, and the presence of oxygen or argon atmosphere.

  一种广泛的3,5-二乙酰基-1,4-二氢吡啶和3,5-二酯基-1,4-二氢吡啶在室温和微波辐射下，通过2,3-二氯-5,6-二氰-p-苯醌（DDQ）被芳构化为吡啶衍生物。本反应提出了一种受电子转移诱导的机制，该机制受溶剂性质、位于1,4-二氢吡啶环的3、4和5位取代基的性质以及氧气或氩气氛围的影响。