3-(5-Chloromethyl-1-methanesulfonyl-4-methoxycarbonylmethyl-1H-pyrrol-3-yl)-propionic acid methyl ester | 127879-97-4

• 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: 3-(5-Chloromethyl-1-methanesulfonyl-4-methoxycarbonylmethyl-1H-pyrrol-3-yl)-propionic acid methyl ester
• 英文别名: Methyl 3-[5-(chloromethyl)-4-(2-methoxy-2-oxoethyl)-1-methylsulfonylpyrrol-3-yl]propanoate
• CAS: 127879-97-4
• 化学式: C₁₃H₁₈ClNO₆S
• 分子量: 351.808
• InChiKey: MPHIRRPTCUKZBV-UHFFFAOYSA-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：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-己硫醇 、 3-(5-Chloromethyl-1-methanesulfonyl-4-methoxycarbonylmethyl-1H-pyrrol-3-yl)-propionic acid methyl ester 生成 methyl 3-[5-(hexylsulfanylmethyl)-4-(2-methoxy-2-oxoethyl)-1-methylsulfonylpyrrol-3-yl]propanoate
  参考文献：
  名称：

  MILLER, ANDREW D.;LEEPER, FINIAN J.;BATTERSBY, ALAN R., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N1, C. 1943-1956

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxymethyl-1-methanesulfonyl-4-[2-(methoxycarbonyl)ethyl]-3-methoxycarbonylmethylpyrrole 在 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以86%的产率得到3-(5-Chloromethyl-1-methanesulfonyl-4-methoxycarbonylmethyl-1H-pyrrol-3-yl)-propionic acid methyl ester
  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

• MILLER, ANDREW D.;LEEPER, FINIAN J.;BATTERSBY, ALAN R., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N1, C. 1943-1956
  作者：MILLER, ANDREW D.、LEEPER, FINIAN J.、BATTERSBY, ALAN R.

  DOI：——

  日期：——
• 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.