4-Oxo-4-(7-oxo-3,4,4a,5,6,7-hexahydro-2H-quinolin-1-yl)-but-2-ynoic acid methyl ester | 80109-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-Oxo-4-(7-oxo-3,4,4a,5,6,7-hexahydro-2H-quinolin-1-yl)-but-2-ynoic acid methyl ester
• 英文别名: methyl 4-oxo-4-(7-oxo-2,3,4,4a,5,6-hexahydroquinolin-1-yl)but-2-ynoate
• CAS: 80109-81-5
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: PXKVMISLXOIECD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-Oxo-1,2,3,4,4a,5,6,7-octahydro-chinolin 以28%的产率得到
  参考文献：
  名称：

  MATOBA, KATSUHIDE;ITOH, KENICHI;KONDO, KAKUYA;YAMAZAKI, TAKAO;NAGATA, MAS+, CHEM. AND PHARM. BULL., 1981, 29, N 9, 2442-2450

  摘要：

  DOI：

文献信息

• Acid-catalyzed cyclization of chalcones derived from various nitrogenous heteroaromatic compounds.
  作者：KATSUHIDE MATOBA、KENICHI ITOH、KAKUYA KONDO、TAKAO YAMAZAKI、MASANORI NAGATA

  DOI：10.1248/cpb.29.2442

  日期：——

  2-(2-Furfurylidene) acetylquinoxaline (Ia) and its 3-methyl analog (Ib) were cyclized to pyrrolo [1, 2-α] quinoxaline ring systems (IIa and IIb) by hydrochloric acid treatment. 2-(4-Methoxybenzylidene) acetylpyridine could be cyclized directly to the 2, 3-dihydroindolizine ring system (V) by treatment with perchloric acid. 2-Arylideneacetyl-3-methyl-quinoxalines (IX) also were cyclized to the corresponding pyrrolo [1, 2-α] quinoxaline systems by hydrochloric acid or perchloric acid. The cyclization of 2-(2-furfurylidene)-acetylquinoline (XI) was performed by using acetic anhydride in the presence of a catalytic amount of trifluoroacetic acid. 2-(2-Furfurylidene) acetylpyrazine (XIII) was cyclized easily by hydrochloric acid treatment. The structures of the adducts of these cyclic products with dimethyl acetylenedicarboxylate are discussed.

  2-(2-呋喃亚甲基)乙酰喹啉（Ia）及其3-甲基类似物（Ib）通过氯化氢处理环化形成吡咯[1, 2-α]喹啉环系（IIa和IIb）。2-(4-甲氧基苄亚甲基)乙酰吡啶可以通过高氯酸处理直接环化为2, 3-二氢喹唑啉环系（V）。2-芳基乙烯乙酰-3-甲基喹唑啉（IX）也通过氯化氢或高氯酸环化为相应的吡咯[1, 2-α]喹啉体系。2-(2-呋喃亚甲基)乙酰喹啉（XI）的环化则使用醋酸酐在微量三氟乙酸的催化下进行。2-(2-呋喃亚甲基)乙酰吡嗪（XIII）通过氯化氢处理容易环化。这些环状产物与二甲基乙炔二羧酸酯的加成物的结构进行了讨论。