(±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-4-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyridone | 1614264-70-8

• 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: (±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-4-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyridone
• 英文别名: 2-cyanoethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 1614264-70-8
• 化学式: C₁₆H₁₅N₃O₅
• 分子量: 329.312
• InChiKey: QRIVJWBITWOYFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-4-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyridone 在 水 、 caesium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (±)-5-(acetoxymethyloxycarbonyl)-6-methyl-4-(3-nitrophenyl)-3,4-dihydro-2-(1H)-pyridone
  参考文献：
  名称：

  Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives

  摘要：

  A series of racemic 4-ary1-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridones have been prepared by means of a modified Hantzsch reaction using commercially available starting materials. An easy removal of the tert-butyl group of these pyridones and subsequent reaction with cesium carbonate and chloromethyl 2-methylpropanoate provided us suitable substrates (+/-)-5 to be used in lipase-catalyzed hydrolysis reactions. Lipase B from Candida antarctica (CAL-B) was the most adequate lipase in the hydrolysis of (+/-)-5. Despite the low enantioselectivity values obtained (E <= 12), several optically active pyridone derivatives were finally isolated with high enantiomeric excesses (ee >= 91%) and moderate yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.012
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 2-cyanoethyl 2-oxobutanoate 、 间硝基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 16.0h， 以51%的产率得到(±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-4-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyridone
  参考文献：
  名称：

  Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives

  摘要：

  A series of racemic 4-ary1-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridones have been prepared by means of a modified Hantzsch reaction using commercially available starting materials. An easy removal of the tert-butyl group of these pyridones and subsequent reaction with cesium carbonate and chloromethyl 2-methylpropanoate provided us suitable substrates (+/-)-5 to be used in lipase-catalyzed hydrolysis reactions. Lipase B from Candida antarctica (CAL-B) was the most adequate lipase in the hydrolysis of (+/-)-5. Despite the low enantioselectivity values obtained (E <= 12), several optically active pyridone derivatives were finally isolated with high enantiomeric excesses (ee >= 91%) and moderate yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.012

文献信息

• Tricyclic and tetracyclic systems acting upon the vascular and central nervous systems
  申请人：Verdecia Reyes Yamila

  公开号：US10138231B2

  公开（公告）日：2018-11-27

  Tricyclic and tetracyclic derivatives of benzodiazepine, pyridodiazepine, and pyrimidodiazepine fused with 1,4-dihydropyridine derivatives are disclosed. The present derivatives can be obtained from derivatives containing a dihydropyridine ring reacting with compounds of the ortho-phenyldiamine, ortho-diaminopyridine, and ortho-diaminopyrimidine type, as well as some subsequent transformations and, tricyclic and tetracyclic derivatives can be obtained with a diazepine or diazepinone nucleus fused to a 1,4-dihydropyridine nucleus, having a substituted or unsubstituted ring of benzene, pyridine or pyrimidine. The present derivatives exhibit vascular and central nervous system therapeutic activity.

  本发明公开了与 1,4-二氢吡啶衍生物融合的苯并二氮卓、吡啶二氮卓和嘧啶二氮卓的三环和四环衍生物。本衍生物可从含有二氢吡啶环的衍生物与原苯二胺、原二氨基吡啶和原二氨基嘧啶类型的化合物反应，以及一些后续的转化过程中获得、可获得三环和四环衍生物，其二氮卓或二氮卓酮核与 1,4-二氢吡啶核融合，具有取代或未取代的苯、吡啶或嘧啶环。本衍生物具有血管和中枢神经系统治疗活性。
• US20140275042A1
  申请人：——

  公开号：US20140275042A1

  公开（公告）日：2014-09-18
• TRICYCLIC AND TETRACYCLIC SYSTEMS ACTING UPON THE VASCULAR AND CENTRAL NERVOUS SYSTEMS
  申请人：CENTRO DE INVESTIGACION Y DESARROLLO DE LOS MEDICAMENTOS (CIDEM)

  公开号：US20190092769A1

  公开（公告）日：2019-03-28

  Tricyclic and tetracyclic derivatives of benzodiazepine, pyridodiazepine, and pyrimidodiazepine fused with 1,4-dihydropyridine derivatives are disclosed. The present derivatives can be obtained from derivatives containing a dihydropyrldine ring reacting with compounds of the ortho-phenyldiamine, ortho-diaminopyridine, and ortho-diaminopyrimidine type, as well as some subsequent transformations and, tricyclic and tetracyclic derivatives can be obtained with a diazepine or diazepinone nucleus fused to a 1,4-dihydropyridine nucleus, having a substituted or unsubstituted ring of benzene, pyridine or pyrimidine. The present derivatives exhibit vascular and central nervous system therapeutic activity.
• Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives
  作者：Susana Y. Torres、Estael Ochoa、Yamila Verdecia、Francisca Rebolledo

  DOI：10.1016/j.tet.2014.05.012

  日期：2014.8

  A series of racemic 4-ary1-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridones have been prepared by means of a modified Hantzsch reaction using commercially available starting materials. An easy removal of the tert-butyl group of these pyridones and subsequent reaction with cesium carbonate and chloromethyl 2-methylpropanoate provided us suitable substrates (+/-)-5 to be used in lipase-catalyzed hydrolysis reactions. Lipase B from Candida antarctica (CAL-B) was the most adequate lipase in the hydrolysis of (+/-)-5. Despite the low enantioselectivity values obtained (E <= 12), several optically active pyridone derivatives were finally isolated with high enantiomeric excesses (ee >= 91%) and moderate yields. (C) 2014 Elsevier Ltd. All rights reserved.