[methylene-2H1]-2-hydroxymethyl-1-methanesulfonyl-4-[2-(methoxycarbonyl)ethyl]-3-methoxycarbonylmethylpyrrole | 216171-25-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [methylene-2H1]-2-hydroxymethyl-1-methanesulfonyl-4-[2-(methoxycarbonyl)ethyl]-3-methoxycarbonylmethylpyrrole
• 英文别名: Methyl 3-[5-[deuterio(hydroxy)methyl]-4-(2-methoxy-2-oxoethyl)-1-methylsulfonylpyrrol-3-yl]propanoate
• CAS: 216171-25-4
• 化学式: C₁₃H₁₉NO₇S
• 分子量: 334.354
• InChiKey: OYQMYYPAVGNYMY-BNEYPBHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [methylene-2H1]-2-hydroxymethyl-1-methanesulfonyl-4-[2-(methoxycarbonyl)ethyl]-3-methoxycarbonylmethylpyrrole 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 49.83h， 生成 methyl 3-[5-[deuterio-[5-(5,5-dimethyl-1,3-dioxan-2-yl)-4-(2-methoxy-2-oxoethyl)-3-(3-methoxy-3-oxopropyl)-1H-pyrrol-2-yl]methyl]-4-(2-methoxy-2-oxoethyl)-1-methylsulfonylpyrrol-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：

  (formyl-d1)-2-formyl-4-[(methoxycarbonyl)ethyl]-3-[(methoxycarbonyl)methyl]pyrrole 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 [methylene-2H1]-2-hydroxymethyl-1-methanesulfonyl-4-[2-(methoxycarbonyl)ethyl]-3-methoxycarbonylmethylpyrrole
  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