2-hexyl-4-methyl-1-methanesulfonylpyrrole | 1326192-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-hexyl-4-methyl-1-methanesulfonylpyrrole
• 英文别名: 2-Hexyl-4-methyl-1-methylsulfonylpyrrole；2-hexyl-4-methyl-1-methylsulfonylpyrrole
• CAS: 1326192-82-8
• 化学式: C₁₂H₂₁NO₂S
• 分子量: 243.37
• InChiKey: SALLHVVOCLTLMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-bromo-1-octyne 在 potassium phosphate 、 四丁基溴化铵 、 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-hexyl-4-methyl-1-methanesulfonylpyrrole
  参考文献：
  名称：

  Nucleophilic Addition of Sulfonamides to Bromoacetylenes: Facile Preparation of Pyrroles

  摘要：

  Nucleophilic addition of sulfonamides to 1-bromo-1-alkynes provided (2)-N-(1-bromo-1-alken-2-yl)-p-toluenesulfonamides in good yield and in a highly regio- and stereoselective manner. Treatment of product (2)-N-(1-bromo-1-octen-2-yl)-N-allyl-p-toluenesulfonamide with a palladium catalyst under Heck conditions afforded 1-(p-toluenesulfonyl)-2-hexyl-4-methylpyrrole in good yield. Other pyrroles with various substituents can also be prepared in good yield by this method.

  DOI：

  10.1021/ol201952b

文献信息

• A Simple and Efficient Protocol to 1,2,4-Substituted Pyrroles via a Sonogashira Coupling-Acid-Catalyzed Cyclization
  作者：Hongwei Zhou、Da Zhu、Jie Zhao、Yuxiu Wei

  DOI：10.1055/s-0030-1261175

  日期：2011.9

  A facile and efficient protocol for the synthesis of 1,2,4-substituted pyrrole derivatives was developed. As a result of the ready availability of materials and the simple operation, this type of reaction should have potential utility in organic synthesis.

  开发了一种简便有效的 1,2,4-取代吡咯衍生物合成方案。由于材料容易获得且操作简单，此类反应在有机合成中具有潜在的用途。
• Nucleophilic Addition of Sulfonamides to Bromoacetylenes: Facile Preparation of Pyrroles
  作者：Masahito Yamagishi、Ken Nishigai、Takeshi Hata、Hirokazu Urabe

  DOI：10.1021/ol201952b

  日期：2011.9.16

  Nucleophilic addition of sulfonamides to 1-bromo-1-alkynes provided (2)-N-(1-bromo-1-alken-2-yl)-p-toluenesulfonamides in good yield and in a highly regio- and stereoselective manner. Treatment of product (2)-N-(1-bromo-1-octen-2-yl)-N-allyl-p-toluenesulfonamide with a palladium catalyst under Heck conditions afforded 1-(p-toluenesulfonyl)-2-hexyl-4-methylpyrrole in good yield. Other pyrroles with various substituents can also be prepared in good yield by this method.