methyl 4-(4-bromophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate | 1334529-05-3

• 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: methyl 4-(4-bromophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate
• CAS: 1334529-05-3
• 化学式: C₁₄H₁₄BrNO₃
• 分子量: 324.174
• InChiKey: DGOLJNDEZYYVAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (±)-4-(4-bromophenyl)-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone 在 Candida antarctica lipase B 、 水 、 caesium carbonate 作用下， 以 甲基叔丁基醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.67h， 生成 methyl 4-(4-bromophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate
  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

• Enantioselective Synthesis of Dihydropyridinones via NHC-Catalyzed Aza-Claisen Reaction
  作者：Benedikt Wanner、Jessada Mahatthananchai、Jeffrey W. Bode

  DOI：10.1021/ol202272t

  日期：2011.10.7

  N-Heterocyclic carbene catalyzed aza-Claisen annulations of enals or their alpha'-hydrozyenone surrogates with vinylogous amides afford dihydropyridinones. The reaction proceeds with a broad range of substrates, and no nitrogen protecting group is required.