2-[[5-(5,5-dimethyl-1,3-dioxan-2-yl)-1H-pyrrol-2-yl]methyl]-1-methylsulfonylpyrrole | 216171-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-[[5-(5,5-dimethyl-1,3-dioxan-2-yl)-1H-pyrrol-2-yl]methyl]-1-methylsulfonylpyrrole
• CAS: 216171-28-7
• 化学式: C₁₆H₂₂N₂O₄S
• 分子量: 338.428
• InChiKey: DBXVHXADWZMXDF-UHFFFAOYSA-N

物化性质

• 沸点：
  524.9±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[5-(5,5-dimethyl-1,3-dioxan-2-yl)-1H-pyrrol-2-yl]methyl]-1-methylsulfonylpyrrole 在 sodium hydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 3.75h， 生成 5-溴-3-氯吲唑
  参考文献：
  名称：

  The Reaction of N-Magnesium Derivatives of Pyrroles with N-Mesylchloromethylpyrroles:  A Synthesis of Dipyrrylmethanes

  摘要：

  Attachment of an alkyl- or arylsulfonyl group at the nitrogen atom of a pyrrole reduces the aromaticity and electron availability of the system. This is confirmed by the structure of an N-tosylated chloromethylpyrrole determined by X-ray crystallography. In agreement, N-mesylated chloromethylpyrroles are handleable materials which react smoothly with N-magnesium derivatives of pyrroles to provide a novel route for synthesis of dipyrrylmethanes. Several examples of this synthesis are described, including the construction of molecules carrying deuterium at the interpyrrolic methylene group.

  DOI：

  10.1021/jo980573i
• 作为产物：
  描述：

  (1-methanesulfonyl-1H-pyrrol-2-yl)methanol 在 甲基碘化镁 、 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.83h， 生成 2-[[5-(5,5-dimethyl-1,3-dioxan-2-yl)-1H-pyrrol-2-yl]methyl]-1-methylsulfonylpyrrole
  参考文献：
  名称：

  The Reaction of N-Magnesium Derivatives of Pyrroles with N-Mesylchloromethylpyrroles:  A Synthesis of Dipyrrylmethanes

  摘要：

  Attachment of an alkyl- or arylsulfonyl group at the nitrogen atom of a pyrrole reduces the aromaticity and electron availability of the system. This is confirmed by the structure of an N-tosylated chloromethylpyrrole determined by X-ray crystallography. In agreement, N-mesylated chloromethylpyrroles are handleable materials which react smoothly with N-magnesium derivatives of pyrroles to provide a novel route for synthesis of dipyrrylmethanes. Several examples of this synthesis are described, including the construction of molecules carrying deuterium at the interpyrrolic methylene group.

  DOI：

  10.1021/jo980573i

文献信息

• The Reaction of N-Magnesium Derivatives of Pyrroles with N-Mesylchloromethylpyrroles:  A Synthesis of Dipyrrylmethanes
  作者：Andrew D. Abell、Brent K. Nabbs、Alan R. Battersby

  DOI：10.1021/jo980573i

  日期：1998.11.1

  Attachment of an alkyl- or arylsulfonyl group at the nitrogen atom of a pyrrole reduces the aromaticity and electron availability of the system. This is confirmed by the structure of an N-tosylated chloromethylpyrrole determined by X-ray crystallography. In agreement, N-mesylated chloromethylpyrroles are handleable materials which react smoothly with N-magnesium derivatives of pyrroles to provide a novel route for synthesis of dipyrrylmethanes. Several examples of this synthesis are described, including the construction of molecules carrying deuterium at the interpyrrolic methylene group.