2-Ethoxycarbonyl-3-methyl-pyrrol-dicarbonsaeure-4,5 | 28991-94-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Ethoxycarbonyl-3-methyl-pyrrol-dicarbonsaeure-4,5
• 英文别名: 5-(ethoxycarbonyl)-4-methyl-1H-pyrrole-2,3-dicarboxylic acid；4-methyl-pyrrole-2,3,5-tricarboxylic acid 5-ethyl ester；5-(Ethoxycarbonyl)-4-methyl-1h-pyrrole-2,3-dicarboxylic acid；5-ethoxycarbonyl-4-methyl-1H-pyrrole-2,3-dicarboxylic acid
• CAS: 28991-94-8
• 化学式: C₁₀H₁₁NO₆
• 分子量: 241.2
• InChiKey: LGUVNZBLWUNCCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Ethoxycarbonyl-3-methyl-pyrrol-dicarbonsaeure-4,5 在 碘 、 碳酸氢钠 、 potassium iodide 作用下， 以 乙醇 、 水 为溶剂， 以14.8 g的产率得到ethyl 4,5-diiodo-3-methyl-1H-pyrrole-2-carboxylate
  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：

  3,5-二(乙氧羰基)-4-甲基-1H-吡咯-2-羧酸 在 硫酸 作用下， 反应 0.33h， 生成 2-Ethoxycarbonyl-3-methyl-pyrrol-dicarbonsaeure-4,5
  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

文献信息

• Imploded bilirubins: synthesis and properties of 10-nor-mesobilirubin-XIIIα and analogs
  作者：Edward B. Nikitin、Sanjeev K. Dey、David A. Lightner

  DOI：10.1007/s00706-008-0034-1

  日期：2009.1

  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.