1-(Ethoxycarbonyl)-3,4-bis(methoxycarbonyl)-2-azabuta-1,3-diene | 163592-54-9

• 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: 1-(Ethoxycarbonyl)-3,4-bis(methoxycarbonyl)-2-azabuta-1,3-diene
• CAS: 163592-54-9
• 化学式: C₁₀H₁₃NO₆
• 分子量: 243.216
• InChiKey: LQBFATWWYLGMDJ-LAVHUSFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  91.26
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-吡咯烷-1-环己烯 、 1-(Ethoxycarbonyl)-3,4-bis(methoxycarbonyl)-2-azabuta-1,3-diene 以 氯仿 为溶剂， 反应 2.0h， 以68%的产率得到Dimethyl 6-(ethoxycarbonyl)-4,5-tetramethylene-4-pyrrolidinyl-1,4,5,6-tetrahydro-2,3-pyridinedicarboxylate
  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
• 作为产物：
  描述：

  乙醛酸乙酯 、 1,1,1-Triphenyl-3,4-bis(methoxycarbonyl)-2-aza-1λ⁵-phosphabuta-1,3-diene 以 氯仿 为溶剂， 反应 4.0h， 生成 1-(Ethoxycarbonyl)-3,4-bis(methoxycarbonyl)-2-azabuta-1,3-diene
  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