dimethyl 7-(2-pyrrolyl)-5,8a-dimethyl-2,3,7,8-tetrahydro-7H-oxazolo<3,2-a>pyridin-6,8-dicarboxylate | 136814-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl 7-(2-pyrrolyl)-5,8a-dimethyl-2,3,7,8-tetrahydro-7H-oxazolo<3,2-a>pyridin-6,8-dicarboxylate
• 英文别名: dimethyl (7S,8S,8aS)-5,8a-dimethyl-7-(1H-pyrrol-2-yl)-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-6,8-dicarboxylate
• CAS: 136814-31-8
• 化学式: C₁₇H₂₂N₂O₅
• 分子量: 334.372
• InChiKey: WJVLFMVJYIMZOE-CPUCHLNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸甲酯 以 甲醇 为溶剂， 反应 48.0h， 生成 dimethyl 7-(2-pyrrolyl)-5,8a-dimethyl-2,3,7,8-tetrahydro-7H-oxazolo<3,2-a>pyridin-6,8-dicarboxylate
  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.
• 2,3,8,8a-Tetrahydro-7H-oxazolo[3,2-a]pyridine: A new heterocyclic system
  作者：Arturo San Feliciano、Esther Caballero、Juan A.P. Pereira、Pilar Puebla

  DOI：10.1016/s0040-4020(01)86577-7

  日期：1991.8

  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.