benzyl 5-(5,5-dimethyl-1,3-dioxan-2-yl)-3-[2-(methoxycarbonyl)ethyl]-4-methoxycarbonylmethylpyrrole-2-carboxylate | 216171-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 5-(5,5-dimethyl-1,3-dioxan-2-yl)-3-[2-(methoxycarbonyl)ethyl]-4-methoxycarbonylmethylpyrrole-2-carboxylate
• 英文别名: benzyl 5-(5,5-dimethyl-1,3-dioxan-2-yl)-4-(2-methoxy-2-oxoethyl)-3-(3-methoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate
• CAS: 216171-20-9
• 化学式: C₂₅H₃₁NO₈
• 分子量: 473.523
• InChiKey: BXTIACNJVODATQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 5-(5,5-dimethyl-1,3-dioxan-2-yl)-3-[2-(methoxycarbonyl)ethyl]-4-methoxycarbonylmethylpyrrole-2-carboxylate 在 palladium on activated charcoal 氢气 、 碘 、 碳酸氢钠 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.75h， 生成 methyl 3-[5-(5,5-dimethyl-1,3-dioxan-2-yl)-2-iodo-4-(2-methoxy-2-oxoethyl)-1H-pyrrol-3-yl]propanoate
  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：

  benzyl 5-formyl-3-(2-methoxycarbonylethyl)-4-methoxycarbonylmethylpyrrole-2-carboxylate 、 2,2-二甲基-1,3-丙二醇 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.75h， 以82%的产率得到benzyl 5-(5,5-dimethyl-1,3-dioxan-2-yl)-3-[2-(methoxycarbonyl)ethyl]-4-methoxycarbonylmethylpyrrole-2-carboxylate
  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.