3,5-diacetyl-4-(3-chlorophenyl)-1,4-dihydro-2,6-dimethylpyridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-diacetyl-4-(3-chlorophenyl)-1,4-dihydro-2,6-dimethylpyridine
• 英文别名: 3,5-diacetyl-4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine；(4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-diyl)diethanone；3,5-diacetyl-2,6-dimethyl-1,4-dihydro-4-(3-chlorophenyl)-3,5-pyridine；1-[5-Acetyl-4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridin-3-yl]ethanone
• 化学式: C₁₇H₁₈ClNO₂
• 分子量: 303.788
• InChiKey: ZUZXKKMJZSIRII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯苯甲醛 、 乙酰丙酮 在 ammonium acetate 、 1-乙基-3-甲基咪唑醋酸盐 作用下， 以 乙醇 为溶剂， 反应 0.58h， 以92%的产率得到3,5-diacetyl-4-(3-chlorophenyl)-1,4-dihydro-2,6-dimethylpyridine
  参考文献：
  名称：

  超声辐照下离子液体[EMIM] OAc合成1,4-二氢吗啡

  摘要：

  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。

  DOI：

  10.1002/jccs.201190041

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。
• 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。
• Reddey, B. Palakshi; Raiesh; Vijayakumar, Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 1, p. 281 - 282
  作者：Reddey, B. Palakshi、Raiesh、Vijayakumar

  DOI：——

  日期：——
• Shinde, D. B.; Shinde, N. D.; Shingare, M. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 10, p. 920 - 922
  作者：Shinde, D. B.、Shinde, N. D.、Shingare, M. S.、Dubey, M. P.、Patnaik, G. K.

  DOI：——

  日期：——
• Synthesis and 3D-QSAR study of 1,4-dihydropyridine derivatives as MDR cancer reverters
  作者：Ashish Radadiya、Vijay Khedkar、Abhay Bavishi、Hardevsinh Vala、Shailesh Thakrar、Dhairya Bhavsar、Anamik Shah、Evans Coutinho

  DOI：10.1016/j.ejmech.2014.01.011

  日期：2014.3

  A series of symmetrical and unsymmetrical 1,4-dihydropyridines were synthesized by a rapid, single pot microwave irradiation (MWI) based protocol along with conventional approach and characterized by NMR, IR and mass spectroscopic techniques. The compounds were evaluated for their tumor cell cytotoxicity in HL-60 tumor cells. A 3D-QSAR study using CoMFA and CoMSIA was carried out to decipher the factors governing MDR reversing ability in cancer. The resulting contour maps derived by the best 3D-QSAR models provide a good insight into the molecular features relevant to the biological activity in this series of analogs. 3D contour maps as a result of 3D-QSAR were utilized to identify some novel features that can be incorporated into the 1,4-dihydropyridine framework to enhance the activity. (C) 2014 Elsevier Masson SAS. All rights reserved.