3,3'-bis(2-carboxyethyl)-4,4'-dimethyl-1H,1H'-2,2'-bipyrrole-5,5'-dicarboxylic acid | 1174908-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,3'-bis(2-carboxyethyl)-4,4'-dimethyl-1H,1H'-2,2'-bipyrrole-5,5'-dicarboxylic acid
• 英文别名: 3,3'-Bis-(2-carboxyethyl)-4,4'-dimethyl-1h,1'h-2,2'-bipyrrole-5,5'-dicarboxylic acid；5-[5-carboxy-3-(2-carboxyethyl)-4-methyl-1H-pyrrol-2-yl]-4-(2-carboxyethyl)-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 1174908-66-7
• 化学式: C₁₈H₂₀N₂O₈
• 分子量: 392.365
• InChiKey: AJYNPXREDGZFHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  181
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3'-bis(2-carboxyethyl)-4,4'-dimethyl-1H,1H'-2,2'-bipyrrole-5,5'-dicarboxylic acid 、 原甲酸三乙酯 在 三氟乙酸 作用下， 反应 2.5h， 生成 diethyl 3,3'-(5,5'-diformyl-4,4'-dimethyl-1H,1'H-[2,2'-bipyrrole]-3,3'-diyl)dipropionate
  参考文献：
  名称：

  Imploded bilirubins: synthesis and properties of 10-nor-mesobilirubin-XIIIα and analogs

  摘要：

  Six 10-nor-bilirubin analogs have been synthesized and investigated. Lacking the C(10) CH2 group, these linear tetrapyrroles have a bipyrrole core rather than a dipyrrylmethane core and thus a different shape. Whereas the propionic acid groups of bilirubin are well engaged in intramolecular hydrogen bonding to the dipyrrinones, molecular modeling studies of the 10-nor-rubins predict that propionic acid chains are too short to engage the CO2H hydrogen fully in intramolecular hydrogen bonding with the dipyrrinones. Butyric acid chains, however, can and do lead to a stabilized conformation with a bipyrrole dihedral angle of approximately 115 degrees. Spectroscopic studies verify the predictions and vapor pressure osmometry indicates that the 10-nor-rubins with butyric acids are monomeric in CHCl3.

  DOI：

  10.1007/s00706-008-0034-1
• 作为产物：
  描述：

  diethyl 3,3'-bis-(2-ethoxycarbonylethyl)-4,4'-dimethyl-2,2'-bipyrrole-5,5'-dicarboxylate 在 水 、 sodium hydroxide 、 硝酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以92%的产率得到3,3'-bis(2-carboxyethyl)-4,4'-dimethyl-1H,1H'-2,2'-bipyrrole-5,5'-dicarboxylic acid
  参考文献：
  名称：

  Imploded bilirubins: synthesis and properties of 10-nor-mesobilirubin-XIIIα and analogs

  摘要：

  Six 10-nor-bilirubin analogs have been synthesized and investigated. Lacking the C(10) CH2 group, these linear tetrapyrroles have a bipyrrole core rather than a dipyrrylmethane core and thus a different shape. Whereas the propionic acid groups of bilirubin are well engaged in intramolecular hydrogen bonding to the dipyrrinones, molecular modeling studies of the 10-nor-rubins predict that propionic acid chains are too short to engage the CO2H hydrogen fully in intramolecular hydrogen bonding with the dipyrrinones. Butyric acid chains, however, can and do lead to a stabilized conformation with a bipyrrole dihedral angle of approximately 115 degrees. Spectroscopic studies verify the predictions and vapor pressure osmometry indicates that the 10-nor-rubins with butyric acids are monomeric in CHCl3.

  DOI：

  10.1007/s00706-008-0034-1