4-[5-acetyl-2-(3-oxo-4-phenylsulfanylbutyl)-1H-pyrrol-3-yl]-1-phenylsulfanylbutan-2-one | 1061162-24-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-[5-acetyl-2-(3-oxo-4-phenylsulfanylbutyl)-1H-pyrrol-3-yl]-1-phenylsulfanylbutan-2-one
• CAS: 1061162-24-0
• 化学式: C₂₆H₂₇NO₃S₂
• 分子量: 465.637
• InChiKey: DGPURXCPEQFBAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙酰基吡咯 、 (phenylsulfanyl)methyl vinyl ketone 在 Fe(ClO₄)3-Al₂O₃ 作用下， 反应 24.0h， 以52%的产率得到4-[5-acetyl-2-(3-oxo-4-phenylsulfanylbutyl)-1H-pyrrol-3-yl]-1-phenylsulfanylbutan-2-one
  参考文献：
  名称：

  Iron Salt-cataltzed Multipoint Alkylation of Pyrrole with Vinyl Ketones

  摘要：

  在 3 摩尔%的四氟硼酸铁（II）或氧化铝支撑的高氯酸铁（III）存在下，吡咯与乙烯基酮发生反应，得到多点烷基化产物，收率很高。最值得注意的是，当 2-乙酰基吡咯与过量的乙烯基酮反应时，可获得 4,5-二烷基化的 2-乙酰基吡咯，收率很高。

  DOI：

  10.1246/cl.2008.794

文献信息

• Development of Solvent-Driven Iron-Catalyzed Reactions
  作者：Toshiyuki Itoh

  DOI：10.3987/rev-16-842

  日期：——

  The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3 similar to 5 mol% of Fe(ClO4)(3)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3-5 mol% of Fe(ClO4)(2)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or alpha-aryl-beta-silylalcohol. In particular, the reaction of chiral alpha-aryl-beta-silylalcohol with indole using Fe(ClO4)(3)center dot nH(2)O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4)(2)/Pybox. We further demonstrated that Fe(ClO4)(3)center dot Al2O3-catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.