methyl 7-(3-nitrophenyl)-5,8a-dimethyl-8-methoxycarbonyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-6-carboxylate | 136814-24-9

• 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 7-(3-nitrophenyl)-5,8a-dimethyl-8-methoxycarbonyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-6-carboxylate
• 英文别名: methyl 7-(3-nitrophenyl)-5,8a-dimethyl-8-methoxycarbonyl-2,3,8,8a-tetrahydro-7H-oxazolo<3,2-a>pyridin-6-carboxylate；dimethyl 7-(3-nitrophenyl)-5,8a-dimethyl-2,3,7,8-tetrahydro-7H-oxazolo<3,2-a>pyridin-6,8-dicarboxylate
• CAS: 136814-24-9
• 化学式: C₁₉H₂₂N₂O₇
• 分子量: 390.393
• InChiKey: HCGSYPRSCGXAIW-TXPKVOOTSA-N

物化性质

• 沸点：
  499.8±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  108.21
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 7-(3-nitrophenyl)-5,8a-dimethyl-8-methoxycarbonyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-6-carboxylate 在 氢氧化钾 、 benzyl(triethyl)ammoniumpermanganate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 间-硝苯地平
  参考文献：
  名称：

  Enantiospecific synthesis of dihydropyridines from chiral enamines

  摘要：

  A new asymmetric synthesis of dihydropyridines is described. This methodology is based on the use of chiral aminoalcohols to produce enamines, which were used in the synthesis of enantiopure 2-alkyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridines. The known stereochemistry of these compounds was exploited to obtain 1,4-dihydropyridines with controlled configuration at C-4. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00239-x
• 作为产物：
  描述：

  乙酰乙酸甲酯 以 甲醇 为溶剂， 反应 48.0h， 生成 methyl 7-(3-nitrophenyl)-5,8a-dimethyl-8-methoxycarbonyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-6-carboxylate
  参考文献：
  名称：

  2,3,8,8a-Tetrahydro-7H-oxazolo[3,2-a]pyridine: A new heterocyclic system

  摘要：

  Compounds with the previously unreported skeleton of 2,3,8,8a-tetrahydro-7H-oxazolo [3,2-a]pyridine were prepared by reactions between alpha,beta-unsaturated ketones or aldehydes and N-hydroxyethylenamines of acetoacetate esters. Other compounds like 1,4-dihydropyridines, aminocyclohexene and cyclohexadiene derivatives were also formed as minor products.

  DOI：

  10.1016/s0040-4020(01)86577-7

文献信息

• Oxazolo[3,2-a]pyridine. A new structural scaffold for the reversal of multi-drug resistance in Leishmania
  作者：Esther Caballero、José Ignacio Manzano、Pilar Puebla、Santiago Castanys、Francisco Gamarro、Arturo San Feliciano

  DOI：10.1016/j.bmcl.2012.07.100

  日期：2012.10

  Compounds belonging to three different classes of fused heterocyclic systems, structurally related to Calcium-channel blockers of the 1,4-dihydropyridine family, were evaluated in their ability to overcome leishmanial resistance to common drugs in a MDR Leishmania tropica strain. Compounds with the skeletal basis of oxazolo[3,2-a]pyridine displayed significant reversion of resistance to daunomycin and miltefosine, with reversion indexes up to 6.7-fold and 8.7-fold, respectively. Most interestingly, the enantiopure compound 20S attained to revert the resistance to both drugs and fairly more significantly than its enantiomer 20R. (C) 2012 Elsevier Ltd. All rights reserved.
• Regiochemistry in the synthesis of 2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridines
  作者：Esther Caballero、Pilar Puebla、Manuel Medarde、Arturo San Feliciano

  DOI：10.1016/s0040-4020(01)80203-9

  日期：1993.1

  The regiochemistry of the reaction between N-hydroxyethyl-enamines and alpha,beta-unsaturated carbonyls and carboxylic esters is discussed. The structure of the 2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridines obtained by this methodology depends on the substituents at the beta-position of the alpha,beta-unsaturated reagent.