methyl 3-methylneoxanthobilirubinate | 148317-93-5

• 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: methyl 3-methylneoxanthobilirubinate
• 英文别名: methyl 3-nor-neoxantobilirubinate
• CAS: 148317-93-5
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: OBAFOIRUHFSAKF-AUWJEWJLSA-N

物化性质

• 沸点：
  513.7±50.0 °C(predicted)
• 密度：
  1.190±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  methyl 3-methylneoxanthobilirubinate 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.5h， 生成 (4Z,20Z)-2,3,7,12-13,18,22,23-octamethyl-(1H,10H,15H,24H,25H,26H,27H,28H,29H)-pentapyrrin-1,24-dione-8,17-dipropanoic acid dimethyl ester
  参考文献：
  名称：

  Synthesis and unusual properties of expanded bilirubin analogs

  摘要：

  DOI：

  10.1016/s0040-4020(01)85333-3
• 作为产物：
  描述：

  3-(4-甲基-1H-吡咯-3-基)丙酸乙酯 在 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 1.5h， 生成 methyl 3-methylneoxanthobilirubinate
  参考文献：
  名称：

  Synthesis and unusual properties of C-(10)-gem-dimethyl bilirubin analogs

  摘要：

  The characteristic thermodynamically-favored intramolecularly hydrogen-bonded conformation adopted by bilirubin pigments is destabilized by substituting methyl groups on the C(10) central methylene. These methyl groups impose conformation-destabilizing methyl-methylene non-bonded steric interactions with the propionic acid beta-CH2 groups at C(8) and C(12) when the propionic acids are engaged in intramolecular hydrogen bonding with the opposing dipyrrinones. Amphiphilic 10,10-dimethylbilirubins (1) and (2) are found to be more polar, but also more soluble than the parents (3) and (4) in organic solvents; yet, H-1-NMR studies in non-polar solvents indicate that a deformed but folded, intramolecularly hydrogen-bonded conformation is retained. The dimethyl esters of 10,10-dimethylbilirubins 1 and 2 did not exhibit the typical strong tendency of bilirubin dimethyl esters to form intermolecular hydrogen bonds in non-polar solvents such as chloroform and benzene.

  DOI：

  10.1016/s0040-4020(01)80362-8