3-allyl-5-methyl-4-phenyl-3-cyano-5-ethoxycarbonyl-1,2,3,4-tetrahydropyridine-2-thione | 137303-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-allyl-5-methyl-4-phenyl-3-cyano-5-ethoxycarbonyl-1,2,3,4-tetrahydropyridine-2-thione
• 英文别名: 5-Allyl-5-cyano-2-methyl-4-phenyl-6-thioxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester；ethyl 5-cyano-2-methyl-4-phenyl-5-prop-2-enyl-6-sulfanylidene-1,4-dihydropyridine-3-carboxylate
• CAS: 137303-40-3
• 化学式: C₁₉H₂₀N₂O₂S
• 分子量: 340.446
• InChiKey: SBPOWAVDBDEKSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-Allylsulfanyl-5-cyano-2-methyl-4-phenyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 反应 20.0h， 以98%的产率得到3-allyl-5-methyl-4-phenyl-3-cyano-5-ethoxycarbonyl-1,2,3,4-tetrahydropyridine-2-thione
  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

• HECTEPOB, V. N.;SHKLOVER, V. E.;STRUCHKOV, YU. T.;SHARANIN, YU. A.;GONCHA+, IZV. AN CCCP. CEP. XIM.,(1991) N, S. 521-523
  作者：HECTEPOB, V. N.、SHKLOVER, V. E.、STRUCHKOV, YU. T.、SHARANIN, YU. A.、GONCHA+

  DOI：——

  日期：——
• Unusual thermal solid-phase rearrangement of 2-allylthio- and 2-allylselenodihydropyridines
  作者：V. N. Nesterov、V. E. Shklover、Yu. T. Struchkov、Yu. A. Sharanin、M. P. Goncharenko、V. D. Dyachenko

  DOI：10.1007/bf00965452

  日期：1991.2

  A previously unreported thermal solid-phase migration of the allyl group was found for 2-allylthio- and 2-allylselenodihydropyridines, leading to 3-allyl-3-cyano-3,4-dihydropyridine-2 (1H)-thiones and -selenones. Analysis of the crystal structures did not indicate whether the solid-phase reaction, which is probably general in nature, is intra- or intermolecular.