Triethyl 6-methyl-5-(methoxycarbonyl)-1,2-dihydro-2,2,3-pyridinetricarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Triethyl 6-methyl-5-(methoxycarbonyl)-1,2-dihydro-2,2,3-pyridinetricarboxylate
• 英文别名: 2-O,2-O',3-O-triethyl 5-O-methyl 6-methyl-1H-pyridine-2,2,3,5-tetracarboxylate
• 化学式: C₁₇H₂₃NO₈
• 分子量: 369.372
• InChiKey: ARPGCKDKZXHZDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  反式-3-(1-吡咯烷酮)丙烯酸乙酯 、 1,1-Bis(ethoxycarbonyl)-3-methyl-4-(methoxycarbonyl)-2-azabuta-1,3-diene 以 氯仿 为溶剂， 反应 74.0h， 以71%的产率得到Triethyl 6-methyl-5-(methoxycarbonyl)-1,2-dihydro-2,2,3-pyridinetricarboxylate
  参考文献：
  名称：

  Synthesis and Reactivity of Electron-Poor 2-Azadienes. [4 + 2] Cycloaddition Reactions with Alkenes and Enamines

  摘要：

  Electron deficient 2-azadienes derived from beta-amino acids 3 are obtained by aza-Wittig reaction of N-vinylic phosphazenes 4 with carbonyl compounds. Inverse electron demand Diels-Alder reaction of azadienes 3 with trans-cyclooctene 7 and cis,trans-cyclooctadiene 8 leads to the formation of trans-cycloalkanotetrahydropyridines 10. Heterodienes 3 also react with enamines 13, 14, and 18 affording pyridine derivatives 16, 17, and 20 in a regioselective fashion. Norbornadiene 11, a less strained olefin than cycloalkenes 7 and 8, requires the presence of lithium perchlorate as catalyst in a nonaqueous solvent like ether, to give cycloadducts 12.

  DOI：

  10.1021/jo00113a017

文献信息

• Synthesis and Reactivity of Electron-Poor 2-Azadienes. [4 + 2] Cycloaddition Reactions with Alkenes and Enamines
  作者：Francisco Palacios、Itziar Perez de Heredia、Gloria Rubiales

  DOI：10.1021/jo00113a017

  日期：1995.4

  Electron deficient 2-azadienes derived from beta-amino acids 3 are obtained by aza-Wittig reaction of N-vinylic phosphazenes 4 with carbonyl compounds. Inverse electron demand Diels-Alder reaction of azadienes 3 with trans-cyclooctene 7 and cis,trans-cyclooctadiene 8 leads to the formation of trans-cycloalkanotetrahydropyridines 10. Heterodienes 3 also react with enamines 13, 14, and 18 affording pyridine derivatives 16, 17, and 20 in a regioselective fashion. Norbornadiene 11, a less strained olefin than cycloalkenes 7 and 8, requires the presence of lithium perchlorate as catalyst in a nonaqueous solvent like ether, to give cycloadducts 12.