4-(2-methoxycarbonylethyl)-3-methyl-3-pyrrolin-2-one | 774-80-1

• 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: 4-(2-methoxycarbonylethyl)-3-methyl-3-pyrrolin-2-one
• 英文别名: 3-(4-methyl-5-oxo-2,5-dihydro-pyrrol-3-yl)-propionic acid methyl ester；3-(4-Methyl-5-oxo-2,5-dihydro-pyrrol-3-yl)-propionsaeure-methylester；methyl 3-(4-methyl-5-oxo-1,2-dihydropyrrol-3-yl)propanoate
• CAS: 774-80-1
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: PRLXADCFSUOONI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-methoxycarbonylethyl)-3-methyl-3-pyrrolin-2-one 在 盐酸 、 甲醇 、 sodium hydroxide 、 zinc diacetate 、 一水合肼 、 sodium nitrite 作用下， 反应 2.0h， 生成 4,3'-Dimethyl-3-vinyl-5(1H)-pyrromethenon-4'-propionsaeure
  参考文献：
  名称：

  Fischer; Plieninger, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1942, vol. 274, p. 231,256

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 4-hydroxy-5-nitro-hexanoate 在 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 为溶剂， 反应 43.33h， 生成 4-(2-methoxycarbonylethyl)-3-methyl-3-pyrrolin-2-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

文献信息

• [EN] METHOD FOR SYNTHESIZING BILIRUBIN<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE BILIRUBINE<br/>[KO] 빌리루빈의 합성 방법
  申请人：[en]BILIX CO., LTD.;[ko]주식회사 빌릭스

  公开号：WO2023018217A1

  公开（公告）日：2023-02-16

  본 발명은 빌리루빈의 합성 방법에 관한 것으로서, 보다 상세하게는 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물을 커플링시켜 화학식 3으로 표시되는 화합물을 제조하는 단계를 포함함으로써 의약품 등으로 유용하게 활용되는 빌리루빈 및 페길화된 빌리루빈을 최초로 화학적으로 합성한 방법에 관한 것이다.