3-(4-(carboxymethyl)-5-formyl-1H-pyrrol-3-yl)propanoic acid | 90923-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-(carboxymethyl)-5-formyl-1H-pyrrol-3-yl)propanoic acid
• 英文别名: 3-Carboxymethyl-4-<2-carboxy-ethyl>-2-formyl-pyrrol；3-(4-carboxymethyl-5-formyl-pyrrol-3-yl)-propionic acid；3-[4-(carboxymethyl)-5-formyl-1H-pyrrol-3-yl]propanoic acid
• CAS: 90923-29-8
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: UGVJJCLRTFGOIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-(carboxymethyl)-5-formyl-1H-pyrrol-3-yl)propanoic acid 在 sodium tetrahydroborate 、 hydroxymethylbilane synthase 、 potassium chloride 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 11.0h， 生成 uroporphyrin I
  参考文献：
  名称：

  Studies on the formation of porphyrinogens from monopyrroles in presence of the enzymes PBG deaminase and/or Uro’gen III synthase

  摘要：

  The substrate-specificities of two enzymes in the biosynthetic pathway to vitamin B-12, PBG deaminase and Uro'gen III synthase, which are involved in the formation of Uro'gen III from the pyrrole PBG, are investigated for the preparation of Uroporphyrin analogs. Both enzymes display strong substrate-specificity. However, tetramerization of pyrroles with carboxylate beta-substituents in mildly basic buffer represents the best and most rapid route to a family of Uro I analogs for enzymatic activity studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.063
• 作为产物：
  描述：

  methyl 3-[5-(difluoromethyl)-4-(2-methoxy-2-oxoethyl)-1-(4-methylphenyl)sulfonylpyrrol-3-yl]propanoate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以27%的产率得到3-(4-(carboxymethyl)-5-formyl-1H-pyrrol-3-yl)propanoic acid
  参考文献：
  名称：

  探测2-二氟甲基吡咯的水解反应性†

  摘要：

  发现α-二氟甲基吡咯是稳定的，同时用吸电子基团进行N-保护。由于吡咯易于接触类氮杂富烯鎓类中间体，因此在水解条件下，α-二氟甲基取代基的C–F键不稳定。如通过对N-保护的β-芳基α-二氟甲基吡咯的脱保护和随后的水解反应的动力学比较所确定的，围绕吡咯环的某些吸电子取代基的存在可以加速该过程。

  DOI：

  10.1039/c6ob01441k

文献信息

• US7189721B2
  申请人：——

  公开号：US7189721B2

  公开（公告）日：2007-03-13
• Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles
  作者：Jennifer A. Melanson、Carlotta Figliola、Deborah A. Smithen、Aleksandra K. Kajetanowicz、Alison Thompson

  DOI：10.1039/c6ob01441k

  日期：——

  α-Difluoromethyl pyrroles were found to be stable while N-protected with an electron-withdrawing group. Due to the propensity of pyrroles to access azafulvenium-like intermediates, the C–F bonds of an α-difluoromethyl substituent are labile under hydrolytic conditions. The presence of certain electron-withdrawing substituents about the pyrrolic ring can accelerate this process, as determined through

  发现α-二氟甲基吡咯是稳定的，同时用吸电子基团进行N-保护。由于吡咯易于接触类氮杂富烯鎓类中间体，因此在水解条件下，α-二氟甲基取代基的C–F键不稳定。如通过对N-保护的β-芳基α-二氟甲基吡咯的脱保护和随后的水解反应的动力学比较所确定的，围绕吡咯环的某些吸电子取代基的存在可以加速该过程。
• Studies on the formation of porphyrinogens from monopyrroles in presence of the enzymes PBG deaminase and/or Uro’gen III synthase
  作者：Clotilde Pichon-Santander、A. Ian Scott

  DOI：10.1016/j.tetlet.2005.10.063

  日期：2005.12

  The substrate-specificities of two enzymes in the biosynthetic pathway to vitamin B-12, PBG deaminase and Uro'gen III synthase, which are involved in the formation of Uro'gen III from the pyrrole PBG, are investigated for the preparation of Uroporphyrin analogs. Both enzymes display strong substrate-specificity. However, tetramerization of pyrroles with carboxylate beta-substituents in mildly basic buffer represents the best and most rapid route to a family of Uro I analogs for enzymatic activity studies. (c) 2005 Elsevier Ltd. All rights reserved.