甲基5-(氯甲酰基)-1H-吡咯-2-羧酸酯 | 347362-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 甲基5-(氯甲酰基)-1H-吡咯-2-羧酸酯
• 英文名称: 5-Chlorocarbonyl-1H-pyrrole-2-carboxylic acid methyl ester
• 英文别名: methyl 5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate；methyl 5-carbonochloridoyl-1H-pyrrole-2-carboxylate
• CAS: 347362-31-6
• 化学式: C₇H₆ClNO₃
• 分子量: 187.583
• InChiKey: VABGUQPFMWYHTM-UHFFFAOYSA-N

物化性质

• 沸点：
  337.0±27.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  甲基5-(氯甲酰基)-1H-吡咯-2-羧酸酯 在 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 60.0h， 生成 diaminomethylidene-[5-[4-[(5-methoxycarbonyl-1H-pyrrole-2-carbonyl)amino]butylcarbamoyl]-1H-pyrrole-2-carbonyl]azanium;chloride
  参考文献：
  名称：

  自折叠分子：由DMSO中的羧酸盐-胍基两性离子形成的界限分明的稳定环

  摘要：

  已经合成了两个两性离子1a，b，其中羧酸根基团通过不同长度的柔性烷基链（分别为丁烯和亚乙基）连接到胍基羰基吡咯阳离子部分上。对于1b，在极性溶液（DMSO）中找不到这两个基团之间的分子内或分子间缔合的迹象。与此相反，1a的1H NMR谱图清楚地表明了羧酸盐与胍基羰基吡咯阳离子之间的强相互作用。根据温度变化和浓度依赖性浓度依赖性NMR研究，这种相互作用源于分子内的络合作用。ROESY和H / D溶剂交换实验表明，即使在DMSO中，1a也会折叠成由多个弱相互作用结合在一起的定义良好的分子内环构象。

  DOI：

  10.1021/jo9915980
• 作为产物：
  描述：

  5-(甲氧羰基)-1H-吡咯-2-羧酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 甲基5-(氯甲酰基)-1H-吡咯-2-羧酸酯
  参考文献：
  名称：

  A highly selective fluorescent probe for pyrophosphate in aqueous solution

  摘要：

  我们合成了一种基于 4-氨基-1,8-萘二甲酰亚胺的新型荧光化学传感器，它含有一个胍基羰基吡咯分子。与水溶液中的 ATP、ADP、AMP 和其他无机阴离子相比，该传感器在焦磷酸的作用下显示出选择性荧光增强。

  DOI：

  10.1039/b808422j

文献信息

• A highly selective fluorescent probe for pyrophosphate in aqueous solution
  作者：Yimin Sun、Cheng Zhong、Rui Gong、Enqin Fu

  DOI：10.1039/b808422j

  日期：——

  A new 4-amino-1,8-naphthalimide-based fluorescent chemosensor bearing a guanidiniocarbonyl pyrrole moiety has been synthesized. The sensor displays a selective fluorescent enhancement with pyrophosphate over ATP, ADP, AMP and other inorganic anions in aqueous solution.

  我们合成了一种基于 4-氨基-1,8-萘二甲酰亚胺的新型荧光化学传感器，它含有一个胍基羰基吡咯分子。与水溶液中的 ATP、ADP、AMP 和其他无机阴离子相比，该传感器在焦磷酸的作用下显示出选择性荧光增强。
• A Ratiometric Fluorescent Chemodosimeter with Selective Recognition for Sulfite in Aqueous Solution
  作者：Yimin Sun、Cheng Zhong、Rui Gong、Honglei Mu、Enqin Fu

  DOI：10.1021/jo9014744

  日期：2009.10.16

  A fluorescent chemodosimeter containing a guanidinio-carbonylpyrrole and a 9-(aminomethyl)anthracene moiety has been synthesized. The sensor exhibits ratiometric fluorescence changes for SO32- over other anions in 90% water/DMSO. The interesting ratiometric fluorescent changes for SO32- are attributed to the fluorescence resonance energy transfer (FRET) and the SO32- complex induced photochemical reaction.
• C−H···O Interactions as Isofunctional Replacements for N−H···O Interactions − Dimer Formation of Methyl 5-Amidopyrrole-2-carboxylates in the Solid State
  作者：Carsten Schmuck、Johann Lex

  DOI：10.1002/1099-0690(200104)2001:8<1519::aid-ejoc1519>3.0.co;2-2

  日期：2001.4

  In the solid state, the chloride salt of methyl 5-amidopyridinium-pyrrole-2-carboxylate (2) forms discrete dimers held together by two rather long N-H...O hydrogen bonds in combination with two short C-H...O interactions between the pyridinium C3-H and the ester CO. Structural and thermodynamic evidence is presented which demonstrates that the observed C-H...O hydrogen bonds are indeed important for bonding in these dimers. A comparison with the solid-state structure of the chloride salt of 5-(guanidiniocarbonyl)pyrrole-2-carboxylic acid (3), which forms similar dimers to 2, reveals that the binding geometries for the two C-H...O contacts in 2.2 are identical to those of two N+-H...O hydrogen bonds in 3.3. According to theoretical calculations the energy associated with these two C-H...O interactions is also similar to that of the two N+-H...O hydrogen bonds as both dimers 2.2 and 3.3 have nearly the same calculated interaction energies. Dimer 3.3 is predicted to be only slightly more stable than 2.2. These data demonstrate that C-H...O interactions can serve as full isofunctional replacements for more conventional N-H...O hydrogen bonds in supramolecular arrangements.
• Fluorescent receptor for dicarboxylates based on pyrrolecarboxamides
  作者：M. Belén Jiménez、Ángel L. Fuentes de Arriba、Emilio Calle、M. Cruz Caballero

  DOI：10.1080/10610278.2012.671523

  日期：2012.5.1

  Neutral ditopic and fluorescent receptor 1 based on two 2,5-pyrrolecarboxamide units shows a strong association with dicarboxylate anions such as glutarate and adipate through multiple hydrogen bonds. Fluorescence and H-1 NMR titrations display a 1: 1 stoichiometry for the complexes, with glutarate as the most strongly bound guest. Receptor 1 exhibits PET-induced fluorescence quenching upon recognition due to the presence of a dansyl group. The synthetic methodology described here might provide access to closely related receptors by the introduction of different fluorophores in the last step of the synthesis.
• Self-Folding Molecules:  A Well Defined, Stable Loop Formed by a Carboxylate−Guanidinium Zwitterion in DMSO
  作者：Carsten Schmuck

  DOI：10.1021/jo9915980

  日期：2000.4.1

  shows clear evidence for a strong interaction between the carboxylate and the guanidiniocarbonyl pyrrole cation. According to variable-temperature and concentration-dependent concentration-dependent NMR studies, this interaction stems from an intramolecular complexation. It was shown by ROESY and H/D-solvent exchange experiments that 1a, even in DMSO, folds into a well-defined intramolecular loop conformation

  已经合成了两个两性离子1a，b，其中羧酸根基团通过不同长度的柔性烷基链（分别为丁烯和亚乙基）连接到胍基羰基吡咯阳离子部分上。对于1b，在极性溶液（DMSO）中找不到这两个基团之间的分子内或分子间缔合的迹象。与此相反，1a的1H NMR谱图清楚地表明了羧酸盐与胍基羰基吡咯阳离子之间的强相互作用。根据温度变化和浓度依赖性浓度依赖性NMR研究，这种相互作用源于分子内的络合作用。ROESY和H / D溶剂交换实验表明，即使在DMSO中，1a也会折叠成由多个弱相互作用结合在一起的定义良好的分子内环构象。