3-(5-Formyl-2-{4-[5-formyl-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-yl]-buta-1,3-diynyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester | 730971-97-8

• 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-Formyl-2-{4-[5-formyl-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-yl]-buta-1,3-diynyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester
• 英文别名: methyl 3-[5-formyl-2-[4-[5-formyl-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]buta-1,3-diynyl]-4-methyl-1H-pyrrol-3-yl]propanoate
• CAS: 730971-97-8
• 化学式: C₂₄H₂₄N₂O₆
• 分子量: 436.464
• InChiKey: UZFPVEZVMNDVBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118.32
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(5-Formyl-2-{4-[5-formyl-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-yl]-buta-1,3-diynyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester 在 sodium hydroxide 、 三丁基膦 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 27.0h， 生成 10,10a,10b,10c-tetradehydro-10a,10b,10c-trishomomesobilirubin-XIIIα
  参考文献：
  名称：

  Novel Linear Tetrapyrroles: Hydrogen Bonding in Diacetylenic Bilirubins

  摘要：

  Bilirubin congeners with dipyrrinones conjoined to a diaceteylene unit (-Cequivalent toC-Cequivalent toC-) rather than to -CH2- were synthesized and examined spectroscopically. This new class of rubrified linear tetrapyrroles cannot easily fold or bend in the middle, but the dipyrrinones can rotate independently about the diacetylene unit. Thus, unlike bilirubin, which is bent in the middle and has a ridge-tile shape, the diacetylene unit orients the attached dipyrrinones along a linear path, and intramolecular hydrogen bonding between the dipyrrinones and opposing carboxylic acids preserves a twisted linear molecular shape when the usual propionic acids are replaced by hexanoic. In a bis-hexanoic acid rubin, the extended planes of the dipyrrinones intersect along the -(Cequivalent toC)(2)- axis at an angle of 102degrees for the conformation stabilized by intramolecular hydrogen bonding. With propionic acid chains, however, neither CO2H can engage an opposing dipyrrinone in intramolecular hydrogen bonding, and the energy-minimum conformation of this linear pigment, shows nearly co-planar dipyrrinones, with an intersection of an angle of similar to180degrees of the extended planes of the dipyrrinones. Spectroscopic evidence for such linearized and twisted (bis-hexanoic) and planar (bis-propionic) structures comes from the pigments' NMR spectral data and their exciton UV-Vis and induced circular dichroism spectra.

  DOI：

  10.1007/s00706-003-0157-3
• 作为产物：
  描述：

  methyl 3-(2-formyl-3-methyl-5-ethynyl-1H-4-pyrrolyl)propanoate 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 、 一氯丙酮 作用下， 以 苯 为溶剂， 反应 20.0h， 以64%的产率得到3-(5-Formyl-2-{4-[5-formyl-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-yl]-buta-1,3-diynyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Novel Linear Tetrapyrroles: Hydrogen Bonding in Diacetylenic Bilirubins

  摘要：

  Bilirubin congeners with dipyrrinones conjoined to a diaceteylene unit (-Cequivalent toC-Cequivalent toC-) rather than to -CH2- were synthesized and examined spectroscopically. This new class of rubrified linear tetrapyrroles cannot easily fold or bend in the middle, but the dipyrrinones can rotate independently about the diacetylene unit. Thus, unlike bilirubin, which is bent in the middle and has a ridge-tile shape, the diacetylene unit orients the attached dipyrrinones along a linear path, and intramolecular hydrogen bonding between the dipyrrinones and opposing carboxylic acids preserves a twisted linear molecular shape when the usual propionic acids are replaced by hexanoic. In a bis-hexanoic acid rubin, the extended planes of the dipyrrinones intersect along the -(Cequivalent toC)(2)- axis at an angle of 102degrees for the conformation stabilized by intramolecular hydrogen bonding. With propionic acid chains, however, neither CO2H can engage an opposing dipyrrinone in intramolecular hydrogen bonding, and the energy-minimum conformation of this linear pigment, shows nearly co-planar dipyrrinones, with an intersection of an angle of similar to180degrees of the extended planes of the dipyrrinones. Spectroscopic evidence for such linearized and twisted (bis-hexanoic) and planar (bis-propionic) structures comes from the pigments' NMR spectral data and their exciton UV-Vis and induced circular dichroism spectra.

  DOI：

  10.1007/s00706-003-0157-3