5-甲酰基-1H-吡咯-2-羧酸苄酯 | 183172-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-甲酰基-1H-吡咯-2-羧酸苄酯
• 英文名称: benzyl 5-formyl-1H-pyrrole-2-carboxylate
• 英文别名: 5-formyl-1H-pyrrole-2-carboxylic acid benzyl ester；Benzyl 5-formylpyrrole-2-carboxylate；Benzyl 5-formyl-1H-pyrrole-2-carboxylate
• CAS: 183172-57-8
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: WLHDCJQRTCXNRP-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  426.6±35.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  5-甲酰基-1H-吡咯-2-羧酸苄酯 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 1,9-Bis(carbobenzoxy)-5-phenyldipyrromethane
  参考文献：
  名称：

  Aryl Ring Rotation in Porphyrins. A Carbon-13 NMR Spin−Lattice Relaxation Time Study

  摘要：

  Overall tumbling and internal rotational motions in porphyrins bearing meso aryl substituents and, in some cases, flanking alkyl groups at the beta-pyrrolic positions have been determined using C-13 spin-lattice relaxation time measurements. In deuteriochloroform solution at 303 K, the overall reorientation of all three porphyrins investigated occurs with diffusion coefficients of similar to 1 x 10(9) s(-1). In porphyrins with only hydrogen at the beta-pyrrolic positions, the meso phenyl rings undergo rotations about their single bonds to the porphyrin with diffusion coefficients of similar to 4 x 10(9) s(-1). Introduction of methyl substituents at the beta-pyrrolic positions adjacent to the phenyl rings reduces these motions, but only to similar to 1 x 10(9) s(-1). Thus, significant internal motions are present in both types of molecules. These motions occur on the time scale of many photoinduced electron and energy transfer processes in porphyrins covalently linked to electron or energy donors or accepters through meso aryl groups. Thus, the internal librational motions may affect rates of photoinduced electron and energy transfer, even in relatively ''rigid'' molecular constructs.

  DOI：

  10.1021/jp962209y
• 作为产物：
  描述：

  吡咯-2-羧酸 在 氢氧化钾 、 三氯氧磷 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 1.93h， 生成 5-甲酰基-1H-吡咯-2-羧酸苄酯
  参考文献：
  名称：

  有效识别单糖的吡咯三足受体。通过广义绑定描述符的亲和力评估

  摘要：

  吡咯和亚氨基 (3) 或氨基 (4) H 键合配体被纳入苯基三足支架，以开发新一代的碳水化合物分子识别受体。受体 3 和 4 有效结合一组生物相关单糖的辛基糖苷，包括葡萄糖 (Glc)、半乳糖 (Gal)、甘露糖 (Man) 和 N-乙酰氨基葡萄糖 (GlcNAc)，在 CDCl3 中显示出微摩尔亲和力，在CD3CN 通过 NMR 滴定。两种受体都选择性地识别所研究的单糖中的 Glc，其中 3 种通常不如 4 种有效，但显示出对 Glc 和 GlcNAc 的全赤道β-糖苷的选择性，这是报道的最大的 H 键合合成受体。CDCl3 中的选择性范围为 3 的近 250 倍和 4 的 30 倍以上。通过 BC50 描述符对亲和力和选择性进行了统一评估，为此描述了一种广义处理，该处理将描述符的范围扩展到包括具有任意数量结合常数的任何双试剂主客体系统。乙腈中 betaGlc 的 ITC 滴定证明，对于

  DOI：

  10.1021/ja068754m

文献信息

• A Facile and Efficient Multi-Gram Synthesis ofN-Protected 5-(Guanidinocarbonyl)-1H-pyrrole-2-carboxylic Acids
  作者：Carsten Schmuck、Volker Bickert、Michael Merschky、Lars Geiger、Daniel Rupprecht、Jürgen Dudaczek、Peter Wich、Thomas Rehm、Uwe Machon

  DOI：10.1002/ejoc.200700756

  日期：2008.1

  The synthesis of two versatile building blocks for supramolecular anion binding motifs, 5-(N-Boc-guanidinocarbonyl)-1H-pyrrole-2-carboxylic acid (1) and 5-(N-Cbz-guanidinocarbonyl)-1H-pyrrole-2-carboxylic acid (2) is reported. Using these building blocks, a guanidiniocarbonyl-pyrrole anion binding site can easily be introduced into more complex molecules by using standard amide coupling conditions

  超分子阴离子结合基序的两种通用构件的合成，5-(N-Boc-guanidinocarbonyl)-1H-pyrrole-2-carboxy acid (1) 和 5-(N-Cbz-guanidinocarbonyl)-1H-pyrrole-2报道了-羧酸(2)。使用这些构建块，可以通过使用标准酰胺偶联条件将胍基羰基-吡咯阴离子结合位点轻松引入更复杂的分子中。两种合成都可以在多克规模上进行。产品以纯净形式获得，可以作为固体储存而不会分解。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Downsizing of Enzymes by Chemical Methods: Arginine Mimics with Low p<i>K</i>_a Values Increase the Rates of Hydrolysis of RNA Model Compounds
  作者：N. Johan V. Lindgren、Lars Geiger、Jesus Razkin、Carsten Schmuck、Lars Baltzer

  DOI：10.1002/anie.200900595

  日期：2009.8.24

  A talented mimic: Large rate enhancements were observed in the catalysis of reactions of RNA models when two arginine residues and two histidine residues were replaced with residues with a guanidiniocarbonyl pyrrole (Gcp) side chain (see structure) in a folded polypeptide catalyst. Gcp fulfilled the functions of, and even outperformed, both Arg and His.

  一个有才华的模仿者：在折叠的多肽催化剂中，当两个精氨酸残基和两个组氨酸残基被胍基羰基吡咯（Gcp）侧链的残基取代时（见结构），在RNA模型反应的催化中观察到速率大大提高。Gcp履行了Arg和His的职能，甚至超越了Arg和His。
• Pyrrole-derivatives as factor Xa inhibitors
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1568698A1

  公开（公告）日：2005-08-31

  The present invention relates to compounds of the formulae I and Ia, wherein R0 ; R1 ; R2 ; R3 ; R4; R22, Q; V, G and M have the meanings indicated in the claims. The compounds of the formulae I and Ia are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is intended. The invention furthermore relates to processes for the preparation of compounds of the formulae I and Ia, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及化合物的公式I和Ia，其中R0; R1; R2; R3; R4; R22，Q; V，G和M具有索赔中指示的含义。公式I和Ia的化合物是有价值的药理活性化合物。它们表现出强烈的抗血栓作用，并适用于治疗和预防心血管疾病，如血栓栓塞疾病或再狭窄。它们是血液凝固酶因子Xa（FXa）和/或因子VIIa（FVIIa）的可逆抑制剂，通常可用于存在因子Xa和/或因子VIIa不良活性或需要抑制因子Xa和/或因子VIIa的治疗或预防的情况。此外，本发明还涉及化合物I和Ia的制备方法，它们的用途，特别是作为药物中的活性成分，以及包含它们的药物制剂。
• Pyrrole-Derivatives as Factor Xa Inhibitors
  申请人：BAUER Armin

  公开号：US20070049573A1

  公开（公告）日：2007-03-01

  The present invention relates to compounds of the formulae (I) and (Ia), wherein R 0 ; R 1 ; R3; R4; R22, Q; V, G and M have the meanings indicated in the claims. The compounds of the formulae (I) and (Ia) are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is intended. The invention furthermore relates to processes for the preparation of compounds of the formulae (I) and (Ia), their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及公式（I）和（Ia）的化合物，其中R0、R1、R3、R4、R22、Q、V、G和M具有所述权利要求中指示的含义。公式（I）和（Ia）的化合物是有价值的药理活性化合物。它们表现出强烈的抗血栓作用，适用于治疗和预防心血管疾病，如血栓栓塞性疾病或再狭窄。它们是血凝酶酶因子Xa（FXa）和/或因子VIIa（FVIIa）的可逆抑制剂，并且通常可用于存在因子Xa和/或因子VIIa的不良活性或预防其发生的情况下，或者用于治疗或预防需要抑制因子Xa和/或因子VIIa的情况。此外，本发明还涉及制备公式（I）和（Ia）的化合物的方法，它们的使用，特别是作为药物中的活性成分，以及包含它们的制药制剂。
• Substituted aminobutyric derivatives as neprilysin inhibitors
  申请人：Novartis AG

  公开号：US08263629B2

  公开（公告）日：2012-09-11

  The present invention provides a compound of formula I′; or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, X and n are defined herein. The invention also relates to a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供公式I′的化合物；或其药学上可接受的盐，其中R1、R2、R3、X和n在此定义。本发明还涉及一种制造本发明化合物的方法及其治疗用途。本发明还提供了一种药理活性剂的组合物和制药组合物。