methyl 3,5-dimethyl-4-([2-(13)C]-2-hydroxyethyl)-1H-pyrrole-2-carboxylate | 1174670-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 3,5-dimethyl-4-([2-(13)C]-2-hydroxyethyl)-1H-pyrrole-2-carboxylate
• CAS: 1174670-00-8
• 化学式: C₁₀H₁₅NO₃
• 分子量: 198.223
• InChiKey: IHRPBIMCWSYXBS-HOSYLAQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.32
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 3,5-dimethyl-4-([2-(13)C]-2-hydroxyethyl)-1H-pyrrole-2-carboxylate 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以85%的产率得到methyl 3,5-dimethyl-4-([2-(13)C]-2-tosyloxyethyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  13C-labeled bilirubin: synthesis of 31(32),171(172)-di-[13C]-mesobilirubin-XIIIα

  摘要：

  The title compound, labeled with C-13 in the ethyl groups was synthesized from (KCN)-C-13 and low-molecular-weight components. The synthetic relay compound was 3(1)(3(2))[C-13]-xanthobilirubinic acid methyl ester in a synthetic route that leads to a label in the ethyl beta-substituent of a dipyrrinone model for bilirubin. This labeled dipyrrinone was oxidatively coupled to the dimethyl ester of mesobiliverdin-XIII alpha, thereby providing a route to a C-13-labeled mesobiliverdin and mesobilirubin, with one carbon of each ethyl being 98% C-13-enriched.

  DOI：

  10.1007/s00706-008-0050-1
• 作为产物：
  描述：

  methyl 3,5-dimethyl-4-[(13)C=O]-carbomethoxymethyl-1H-pyrrole-2-carboxylate 在 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 以91%的产率得到methyl 3,5-dimethyl-4-([2-(13)C]-2-hydroxyethyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  13C-labeled bilirubin: synthesis of 31(32),171(172)-di-[13C]-mesobilirubin-XIIIα

  摘要：

  The title compound, labeled with C-13 in the ethyl groups was synthesized from (KCN)-C-13 and low-molecular-weight components. The synthetic relay compound was 3(1)(3(2))[C-13]-xanthobilirubinic acid methyl ester in a synthetic route that leads to a label in the ethyl beta-substituent of a dipyrrinone model for bilirubin. This labeled dipyrrinone was oxidatively coupled to the dimethyl ester of mesobiliverdin-XIII alpha, thereby providing a route to a C-13-labeled mesobiliverdin and mesobilirubin, with one carbon of each ethyl being 98% C-13-enriched.

  DOI：

  10.1007/s00706-008-0050-1