4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline | 912561-76-3

• 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: 4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline
• 英文别名: 3-(2-chloroprop-2-en-1-yl)-2-methylquinolin-4-ol；4-Hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline；3-(2-chloroprop-2-enyl)-2-methyl-1H-quinolin-4-one
• CAS: 912561-76-3
• 化学式: C₁₃H₁₂ClNO
• 分子量: 233.697
• InChiKey: YBQQGHWOLIOWJN-UHFFFAOYSA-N

物化性质

• 熔点：
  272 °C(Solv: ethanol (64-17-5))
• 沸点：
  382.7±42.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline 在 sodium hydroxide 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 3-(2-chloroprop-2-en-1-yl)-2-methyl-1H-quinoline-4-thione
  参考文献：
  名称：

  Synthesis of substituted 2,4-dimethylthieno[3,2-c]quinolines

  摘要：

  A procedure was developed for the synthesis of substituted 2,4-dimethylthieno[3,2-c]quinolines via intramolecular cyclization and subsequent arornatization of 3-(2-chloroprop-2-en-1-yl)- and 3-(2-oxopropyl)-2methylquinoline-4-thiols. The latter were obtained by alkaline hydrolysis of the corresponding thiuroniurn salts which were prepared in turn by reactions of 4-chloro-3-(2-chloroprop-2-en-1-yi)- and 4-chloro-3-(2-oxopropyl)-2-methylquinolines with thiourea.

  DOI：

  10.1134/s1070428007030165
• 作为产物：
  描述：

  4-羟基-2-甲基喹啉 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline
  参考文献：
  名称：

  Synthesis and modification of 4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline

  摘要：

  4-Hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline was prepared by O-allylation of 4-hydroxy-2-methylquinoline followed by the Claisen rearrangement of the 2-methyl-4-(2-chloro-2-propenyloxy)quinoline obtained. Chemical modifications of 4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline resulted in the synthesis of 4-amino-2-methyl-3-(2-methyl-3-indolyl)quinoline.

  DOI：

  10.1134/s1070428006050150

文献信息

• Synthesis of 2-bromomethyl-4-methyl-2,3-dihydrofuro[3,2-c]-quinoline and some its transformations
  作者：A. A. Avetisyan、I. L. Aleksanyan、K. S. Sargsyan

  DOI：10.1134/s1070428007030177

  日期：2007.3

  Electrophilic intramolecular heterocyclization of 3-(2-chloroprop-2-en-1-yl)-2-methylquinolin-4-ol by the action of bromine gave 2-bromomethyl-2-chloro-4-methyl-2,3-dihydrofuro[3,2-clquinoline hydrobromide which was converted into 2-hydroxymethyl-, 2-alkoxymethyl-, and 2-dialkylaminomethyl-4-methylfuro[3,2-c]quinolines by treatment with the corresponding nucleophiles.
• Synthesis and modification of 4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline
  作者：A. A. Avetisyan、I. L. Aleksanyan、A. A. Pivazyan

  DOI：10.1134/s1070428006050150

  日期：2006.5

  4-Hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline was prepared by O-allylation of 4-hydroxy-2-methylquinoline followed by the Claisen rearrangement of the 2-methyl-4-(2-chloro-2-propenyloxy)quinoline obtained. Chemical modifications of 4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline resulted in the synthesis of 4-amino-2-methyl-3-(2-methyl-3-indolyl)quinoline.
• Synthesis of substituted 2,4-dimethylthieno[3,2-c]quinolines
  作者：A. A. Avetisyan、I. L. Aleksanyan、K. S. Sargsyan

  DOI：10.1134/s1070428007030165

  日期：2007.3

  A procedure was developed for the synthesis of substituted 2,4-dimethylthieno[3,2-c]quinolines via intramolecular cyclization and subsequent arornatization of 3-(2-chloroprop-2-en-1-yl)- and 3-(2-oxopropyl)-2methylquinoline-4-thiols. The latter were obtained by alkaline hydrolysis of the corresponding thiuroniurn salts which were prepared in turn by reactions of 4-chloro-3-(2-chloroprop-2-en-1-yi)- and 4-chloro-3-(2-oxopropyl)-2-methylquinolines with thiourea.