1-Cyano-1,3-dimethyl-4-(methoxycarbonyl)-2-azabuta-1,3-diene | 152976-02-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-Cyano-1,3-dimethyl-4-(methoxycarbonyl)-2-azabuta-1,3-diene
• CAS: 152976-02-8
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: FDIDRHOIEWVPBT-AGLLBGTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.45
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z,E)-1,5-cyclooctadiene 、 1-Cyano-1,3-dimethyl-4-(methoxycarbonyl)-2-azabuta-1,3-diene 以 氯仿 为溶剂， 反应 20.0h， 以70%的产率得到Dimethyl 2-cyano-trans-3,4-(cis-3-hexenylene)-1,2,3,4-tetrahydro-2,6-dimethyl-5-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：

  (E)-3-azido-but-2-enoic acid methyl ester 以 二氯甲烷 为溶剂， 生成 1-Cyano-1,3-dimethyl-4-(methoxycarbonyl)-2-azabuta-1,3-diene
  参考文献：
  名称：

  Preparation and reactivity of electron-poor 2-azadienes. Diels-Alder reaction with trans-cyclooctene.

  摘要：

  Di-, tri- and tetra- substituted 2-azadienes 3 underbar with electron withdrawing groups have been obtained by Aza-Wittig reaction of N-vinylic phosphazenes with carbonyl compounds. The Diels-Alder reaction of 3 underbar with trans-cyclooctene has also been explored.

  DOI：

  10.1016/s0040-4039(00)79357-9