3-allyl-4-(4-bromophenyl)-7,7-dimethyl-5-oxo-2-phenacylthio-3-cyano-3,4,5,6,7,8-hexahydroquinoline | 137303-43-6

• 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: 3-allyl-4-(4-bromophenyl)-7,7-dimethyl-5-oxo-2-phenacylthio-3-cyano-3,4,5,6,7,8-hexahydroquinoline
• 英文别名: 4-(4-Bromophenyl)-7,7-dimethyl-5-oxo-2-[(2-oxo-2-phenylethyl)sulfanyl]-3-(prop-2-en-1-yl)-3,4,5,6,7,8-hexahydroquinoline-3-carbonitrile；4-(4-bromophenyl)-7,7-dimethyl-5-oxo-2-phenacylsulfanyl-3-prop-2-enyl-6,8-dihydro-4H-quinoline-3-carbonitrile
• CAS: 137303-43-6
• 化学式: C₂₉H₂₇BrN₂O₂S
• 分子量: 547.516
• InChiKey: UJXDTAVPQGUZOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  95.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-Allylsulfanyl-4-(4-bromo-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-allyl-4-(4-bromophenyl)-7,7-dimethyl-5-oxo-2-phenacylthio-3-cyano-3,4,5,6,7,8-hexahydroquinoline
  参考文献：
  名称：

  Synthesis and regioselectivity of the [3,3]-sigmatropic rearrangement of substituted 2-allylthio- and 2-allylseleno-1,4-dihydropyridines

  摘要：

  The reaction of 3-cyano-1,4-dihydropyridine-2-thiolates and the corresponding selenolates with allyl bromide gave 2-allylthio- and 2-allylseleno-3-cyano-1,4-dihydropyridines, which, upon heating in various solvents or in the solid state, undergo [3,3]-sigmatropic rearrangement to give 3-cyano-3-allyl-1,2,3,4-tetrahydropyridine-2-thiones and the corresponding selenones. The resultant pyridinethiones are alkylated by alkyl halides at the sulfur atom and are oxidized by iodine to give disulfides.

  DOI：

  10.1007/bf01172273

文献信息

• Synthesis and regioselectivity of the [3,3]-sigmatropic rearrangement of substituted 2-allylthio- and 2-allylseleno-1,4-dihydropyridines
  作者：V. P. Litvinov、Yu. A. Sharanin、M. P. Goncharenko、V. D. Dyachenko、A. M. Shestopalov

  DOI：10.1007/bf01172273

  日期：1991.8

  The reaction of 3-cyano-1,4-dihydropyridine-2-thiolates and the corresponding selenolates with allyl bromide gave 2-allylthio- and 2-allylseleno-3-cyano-1,4-dihydropyridines, which, upon heating in various solvents or in the solid state, undergo [3,3]-sigmatropic rearrangement to give 3-cyano-3-allyl-1,2,3,4-tetrahydropyridine-2-thiones and the corresponding selenones. The resultant pyridinethiones are alkylated by alkyl halides at the sulfur atom and are oxidized by iodine to give disulfides.