methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylate | 420119-23-9

• 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: methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylate
• 英文别名: Methyl 1,2,7,7a-tetrahydrocyclopropa[b]quinoline-1a-carboxylate
• CAS: 420119-23-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: DJYBWNNAPJSPOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylate 在 氨 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.5h， 生成 2-phenyl-4a,5-dihydro-1H,4H-cyclopropa[e]imidazo[1,5-a]quinoline-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis of 1,2,7,7a-Tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic Acid Derivatives, Doubly Constrained ACC Derivatives, by a Remarkable Cyclopropanation Process

  摘要：

  Reaction of N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid with acetic anhydride resulted in 1H,3H,5H-oxazolo[3,4-a]quinolin-3-one derivative 13. Different cyclopropanation processes were applied to 13, but only diazomethane in the presence of water furnished the hitherto unknown methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-la-carboxylate 14, which can be considered as a doubly constrained 1-aminocyclopropane-1-carboxylic acid system. The mechanism of the cyclopropanation was studied in detail. The new ACC ester 14 was transformed into fused tetracyclic hydantoin derivatives, which comprised a new type of heterocyclic system.

  DOI：

  10.1021/jo010993z
• 作为产物：
  描述：

  N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid 以 乙醚 、 乙酸酐 为溶剂， 反应 49.0h， 生成 methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylate
  参考文献：
  名称：

  Synthesis of 1,2,7,7a-Tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic Acid Derivatives, Doubly Constrained ACC Derivatives, by a Remarkable Cyclopropanation Process

  摘要：

  Reaction of N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid with acetic anhydride resulted in 1H,3H,5H-oxazolo[3,4-a]quinolin-3-one derivative 13. Different cyclopropanation processes were applied to 13, but only diazomethane in the presence of water furnished the hitherto unknown methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-la-carboxylate 14, which can be considered as a doubly constrained 1-aminocyclopropane-1-carboxylic acid system. The mechanism of the cyclopropanation was studied in detail. The new ACC ester 14 was transformed into fused tetracyclic hydantoin derivatives, which comprised a new type of heterocyclic system.

  DOI：

  10.1021/jo010993z