(Z)-8-ethyl-3-(2-methoxycarbonylethyl)-2,7,9-trimethyl-(10H)-dipyrrin-1-one | 942294-41-9

• 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: (Z)-8-ethyl-3-(2-methoxycarbonylethyl)-2,7,9-trimethyl-(10H)-dipyrrin-1-one
• CAS: 942294-41-9
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: ZSLYLPGFVCYDIF-SXGWCWSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  71.19
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-8-ethyl-3-(2-methoxycarbonylethyl)-2,7,9-trimethyl-(10H)-dipyrrin-1-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以81%的产率得到(Z)-3-(2-carboxyethyl)-8-ethyl-2,7,9-trimethyl-(10H)-dipyrrin-1-one
  参考文献：
  名称：

  Synthesis and Hepatic Metabolism of Xanthobilirubinic Acid Regioisomers

  摘要：

  A set of four regioisomeric dipyrrinone propionic acids has been synthesized and their hepatic metabolism examined in rats: xanthobilirubinic acid and pseudo-xanthobilirubinic acid each with a propionic acid on a pyrrole ring; exo-psi-xanthobilirubinic acid and endo-psi-xanthobilirubinic acid, each with a propionic acid transposed to a lactam ring. After intravenous injection all four isomers were excreted to some degree in unchanged form in bile in normal rats. Xanthobilirubinic acid, the structurally closest dipyrrinone to bilirubin, and exo-psi-xanthobilirubinic acid were excreted almost entirely in unchanged form. However, a small fraction of xanthobilirubinic acid acyl glucuronide was also detected. More extensive acyl glucuronidation was observed for pseudo-xanthobilirubinic acid, and endo-psi-xanthobilirubinic acid underwent slow metabolism to unidentified more polar products that did not seem to be glucuronides.

  DOI：

  10.1007/s00706-006-0543-8
• 作为产物：
  描述：

  methyl 4-hydroxy-5-nitro-hexanoate 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 phenyl-N,N,N-trimethylammonium tribromide 、 三氟乙酸 、 四甲基胍 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 异丙醇 、 乙腈 为溶剂， 反应 127.33h， 生成 (Z)-8-ethyl-3-(2-methoxycarbonylethyl)-2,7,9-trimethyl-(10H)-dipyrrin-1-one
  参考文献：
  名称：

  Synthesis and Hepatic Metabolism of Xanthobilirubinic Acid Regioisomers

  摘要：

  A set of four regioisomeric dipyrrinone propionic acids has been synthesized and their hepatic metabolism examined in rats: xanthobilirubinic acid and pseudo-xanthobilirubinic acid each with a propionic acid on a pyrrole ring; exo-psi-xanthobilirubinic acid and endo-psi-xanthobilirubinic acid, each with a propionic acid transposed to a lactam ring. After intravenous injection all four isomers were excreted to some degree in unchanged form in bile in normal rats. Xanthobilirubinic acid, the structurally closest dipyrrinone to bilirubin, and exo-psi-xanthobilirubinic acid were excreted almost entirely in unchanged form. However, a small fraction of xanthobilirubinic acid acyl glucuronide was also detected. More extensive acyl glucuronidation was observed for pseudo-xanthobilirubinic acid, and endo-psi-xanthobilirubinic acid underwent slow metabolism to unidentified more polar products that did not seem to be glucuronides.

  DOI：

  10.1007/s00706-006-0543-8