3-hydroxy-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester | 15431-56-8

• 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-hydroxy-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 3-hydroxy-4-methyl-pyrrole-2-carboxylate；3-Hydroxy-4-methyl-pyrrol-2-carbonsaeure-ethylester；3-hydroxy-4-methyl-pyrrole-2-carboxylic acid ethyl ester；3-Hydroxy-4-methyl-pyrrol-2-carbonsaeure-aethylester；ethyl 3-hydroxy-4-methyl-1H-pyrrole-2-carboxylate
• CAS: 15431-56-8
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: SYWUITFNCHBJHH-UHFFFAOYSA-N

物化性质

• 沸点：
  286.7±35.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester 在 sodium hydroxide 、 甲酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 反应 145.0h， 生成 ethyl 5-[tert-butoxycarbonylamino-(toluene-4-sulfonyl)methyl]-3-methoxy-4-methyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  甲氧基吡咯氨基酸（MOPAS）的合成和肽结合特性。

  摘要：

  [结构：见正文]甲氧基吡咯氨基酸（MOPAS）已制备，并被引入具有发夹结构的小肽中。通过NMR滴定和X射线晶体结构分析研究了该模仿二肽β-链的杂环氨基酸的分子内和分子间结合特性。数据揭示了与肽β-折叠互补的氢键模式。

  DOI：

  10.1021/ol049855x
• 作为产物：
  描述：

  β-(ethoxycarbonylmethyl-amino)-isobutyric acid ethyl ester 在 氢化钾 、 甲苯 作用下， 生成 3-hydroxy-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  78. 2-甲基吡咯烷啶的合成

  摘要：

  DOI：

  10.1039/jr9420000424

文献信息

• SUBSTITUTED [(5H-PYRROLO[2,1-c][1,4]BENZODIAZEPIN-11-YL)PIPERAZIN-1-YL]-2,2-DIMETHYLPROPANOIC ACID COMPOUNDS AS DUAL ACTIVITY H1 INVERSE AGONISTS/5-HT2A ANTAGONISTS
  申请人：CAMP Anne Marie

  公开号：US20120202797A1

  公开（公告）日：2012-08-09

  A dual H1/5-HT 2A receptor antagonist of the formula: its uses, and methods for its preparation are described.

  一种双重H1/5-HT2A受体拮抗剂的公式、用途和制备方法被描述。
• Synthesis of 3-Oxo-2,3-dihydropyrrole Amino Acids as Chiral Dipeptidomimics
  作者：Burkhard König、Prantik Maity

  DOI：10.1055/s-2006-942497

  日期：2006.8

  We describe the synthesis of a novel chiral dipeptide β-sheet mimic based on aminomethyl-3-oxo-2,3-dihydropyrrole carboxylic acids. The synthesis uses a palladium-catalyzed allylation with the chiral Trost ligand as a key step for the construction of a quaternary chiral center. This allows the enantioselective conversion of 2-carboxy-3-hydroxy-pyrrole into 3-oxo-2,3-dihydropyrrole-2-allyl-2-carboxylate. The allyl group is subsequently converted into an aldehyde or ester group. Peptide coupling of the 3-oxo-2,3-dihydropyrrole amino acid leads to more extended systems with partially constrained dipeptide units.

  我们描述了基于氨甲基-3-氧代-2,3-二氢吡咯羧酸的新型手性二肽β-片模拟物的合成。该合成采用钯催化的手性 Trost 配体烯丙基化作为构建四级手性中心的关键步骤。这使得2-羧基-3-羟基-吡咯对映选择性转化为3-氧代-2,3-二氢吡咯-2-烯丙基-2-羧酸酯。随后将烯丙基转化为醛基或酯基。 3-氧代-2,3-二氢吡咯氨基酸的肽偶联导致具有部分受限二肽单元的更扩展的系统。
• The chemistry of pyrrolic compounds. IV. β-Hydroxy- and β-Methoxypyrroles
  作者：R Chong、PS Clezy

  DOI：10.1071/ch9670935

  日期：——

  Some aspects of the chemistry of β-hydroxypyrroles and their methyl ethers are described, with particular reference to the development of pyrrolic intermediates suitable for the synthesis of porphyrins carrying this type of substituent. Tautomerism in the β-hydroxypyrroles is discussed.

  介绍了 描述了 β-羟基吡咯及其甲基醚化学的一些方面，特别是 特别提到了吡咯中间体的开发，这种中间体适合于合成带有这种取代基的卟啉。 的吡咯中间体的开发。在 讨论了 β-羟基吡咯中的同分异构现象。
• Substituted [(5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid compounds as dual activity H1 inverse agonists/5-HT2A antagonists
  申请人：Eli Lilly and Company

  公开号：US08314092B2

  公开（公告）日：2012-11-20

  A dual H1/5-HT2A receptor antagonist of the formula: its uses, and methods for its preparation are described.

  本文描述了一种化学式为H1/5-HT2A双重受体拮抗剂的用途和制备方法。
• Synthesis and structure of a heterocyclic ansa pyrrole amino acid
  作者：Georg Dirscherl、Parham Rooshenas、Peter R. Schreiner、Frédéric Lamaty、Burkhard König

  DOI：10.1016/j.tet.2008.01.061

  日期：2008.3

  We report a synthetic route to ansa pyrrole amino acids via olefin ring-closing metathesis of diene precursors in the presence of Grubbs I catalyst. The dienes were prepared by Grignard addition to pyrrole sulfinyl imines. The success of the macrocyclic ring closure depends oil the dienes structure and only in the case of the 13-membered compound 28 sufficient material could be isolated by preparative HPLC separation to investigate its structure spectroscopically. As also rationalized by our computations at the B3LYP/6-311+G(d,p)//B3LYP/6-31G(d) level of theory, 28 is configurationally stable. (C) 2008 Elsevier Ltd. All rights reserved.