N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid | 73717-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid
• 英文别名: 1-benzoyl-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid；1-Benzoyl-1,2,3,4-tetrahydro-chinolin-2-carbonsaeure；1-Benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid；1-benzoyl-3,4-dihydro-2H-quinoline-2-carboxylic acid
• CAS: 73717-41-6
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: MACVDZXFYDRIDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid 以 乙醚 、 乙酸酐 、 甲苯 为溶剂， 反应 49.0h， 生成 methyl 2-propylaminocarbonyl-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
• 作为产物：
  描述：

  methyl N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylate 在 5percent NaOH 作用下， 以 甲醇 为溶剂， 反应 5.5h， 以74%的产率得到N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid
  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

文献信息

• Wieland; Hettche; Hoshino, Chemische Berichte, 1928, vol. 61, p. 2378
  作者：Wieland、Hettche、Hoshino

  DOI：——

  日期：——
• The Catalytic Hydrogenation of the Reissert Compound and Hydrolysis of the Product
  作者：Raymond F. Collins

  DOI：10.1021/ja01623a070

  日期：1955.9
• Zecchini,G.P.; Paradisi,M.P., Journal of Heterocyclic Chemistry, 1979, vol. 16, p. 1589 - 1597
  作者：Zecchini,G.P.、Paradisi,M.P.

  DOI：——

  日期：——
• The Reaction of Reissert Compounds and Related 1-Acyl-1,2-dihydroquinoline Derivatives¹
  作者：R. F. Collins、T. Henshall

  DOI：10.1021/ja01534a042

  日期：1958.1
• Synthesis of 1,2,7,7a-Tetrahydro-1a<i>H</i>-cyclopropa[<i>b</i>]quinoline-1a-carboxylic Acid Derivatives, Doubly Constrained ACC Derivatives, by a Remarkable Cyclopropanation Process
  作者：Zsolt Szakonyi、Ferenc Fülöp、Dirk Tourwé、Norbert De Kimpe

  DOI：10.1021/jo010993z

  日期：2002.4.1

  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.