ethyl 1-(4-methoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate | 723303-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-(4-methoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 1-(4-methoxyphenyl)-2-methyl-5-phenylpyrrole-3-carboxylate
• CAS: 723303-24-0
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: UHTUMAZIUITHLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  489.0±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-methoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate 在 氧气 、 二甲基亚砜 作用下， 反应 1.0h， 生成 ethyl 2-formyl-1-(4-methoxyphenyl)-5-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  氧化环化和C sp 3–H直接氧化为C═O合成吡咯-2-甲醛衍生物

  摘要：

  提出了一种高效且实用的从头合成吡咯-2-甲醛骨架的方法，该骨架具有氧化环化反应和C sp 3–H到C═O氧化反应，以由芳基甲基酮，芳基胺和乙酰乙酸酯。初步的机理研究表明，醛中的氧原子起源于氧。此外，已开发的可扩展方法相对于C–H部分的传统氧化功能化具有明显优势，避免了使用化学计量的危险氧化剂。

  DOI：

  10.1021/acs.orglett.7b03821
• 作为产物：
  描述：

  苯乙酮 在 碘 、 二甲基亚砜 、 copper dichloride 作用下， 反应 2.0h， 生成 ethyl 1-(4-methoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  氧化环化和C sp 3–H直接氧化为C═O合成吡咯-2-甲醛衍生物

  摘要：

  提出了一种高效且实用的从头合成吡咯-2-甲醛骨架的方法，该骨架具有氧化环化反应和C sp 3–H到C═O氧化反应，以由芳基甲基酮，芳基胺和乙酰乙酸酯。初步的机理研究表明，醛中的氧原子起源于氧。此外，已开发的可扩展方法相对于C–H部分的传统氧化功能化具有明显优势，避免了使用化学计量的危险氧化剂。

  DOI：

  10.1021/acs.orglett.7b03821

文献信息

• [EN] 1,5-DIARYL-PYRROLE-3-CARBOXAMIDE DERIVATIVES AND THEIR USE AS CANNABINOID RECEPTOR MODULATORS<br/>[FR] DERIVES DE 1,5-DIARYL-PYRROLE-3-CARBOXAMIDE ET LEUR UTILISATION EN TANT QUE MODULATEURS DES RECEPTEURS DES CANNABINOIDES
  申请人：ASTRAZENECA AB

  公开号：WO2004058249A1

  公开（公告）日：2004-07-15

  The present invention relates to a compound of formula (I) (A chemical formula should be inserted here - please see paper copy enclosed herewith) in which R1 and R2 independently represent phenyl, thienyl or pyridyl each of which is optionally substituted by one, two or three groups represented by Z; and R3 is H, a C1-3alkyl group, a C1-3alkoxymethyl group, trifluoromethyl, a hydroxyC1-3alkyl group, an aminoC1-3alkyl group, C1-3alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C1-3alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula -CONHNRaRb wherein Ra and Rb are as defined for R4 and R5 respectively; X is CO or SO2 ; Y is absent or represents NH optionally substituted by a C1-3alkyl group; R4 and R5 independently represent: a C1-6alkyl group; an (amino)C1-4alkyl- group in which the amino is optionally substituted by one or more C1-3alkyl groups; an optionally substituted non-aromatic C3-15carbocyclic group; a (C3-12cycloalkyl)C1-3alkyl- group; a group -(CH2)r(phenyl )s; naphthyl; anthracenyl; a saturated 5 to 8 membered heterocyclic group containing one nitrogen and optionally one of the following: oxygen, sulphur or an additional nitrogen wherein the heterocyclic group is optionally substituted ;1-adamantylmethyl; a group - (CH2)t Het where Het represents an aromatic heterocycle optionally substituted; or R4 represents H and R5 is as defined above; or R4 and R5 together with the nitrogen atom to which they are attached represent a saturated 5 to 8 membered heterocyclic group; R6 is H, a C1-3alkyl group, a C1-3alkoxymethyl group, trifluoromethyl, a hydroxyC1-3alkyl group, C1-3alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C1-3alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula -CONHNRaRb ; with provisos; to processes for preparing such compounds, to their use in the treatment of obesity, psychiatric and neurological disorders particularly obesity, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  本发明涉及一种化合物，其化学式为（I），其中R1和R2分别独立表示苯基，噻吩基或吡啶基，每个基上均可选择性地取代一个、两个或三个由Z表示的基团；R3为H，C1-3烷基基团，C1-3烷氧甲基基团，三氟甲基，羟基C1-3烷基基团，氨基C1-3烷基基团，C1-3烷氧羰基，羧基，氰基，氨基甲酰基，一级或二级C1-3烷基甲酰基，乙酰基或化学式为-CONHNRaRb的肼基，其中Ra和Rb分别定义为R4和R5；X为CO或SO2；Y为空或表示NH，该氮原子可选择性地取代为C1-3烷基基团；R4和R5独立地表示：C1-6烷基基团；（氨基）C1-4烷基基团，其中氨基可选择性地取代为一个或多个C1-3烷基基团；可选择性取代的非芳香性C3-15碳环基团；（C3-12环烷基）C1-3烷基基团；基团-(CH2)r(苯) s；萘基；蒽基；含有一个氮原子并可选择性地含有以下之一的饱和的5到8个成员的杂环基团：氧，硫或另一个氮原子，其中杂环基团可选择性地取代；1-金刚烷基甲基；基团-(CH2)t Het，其中Het表示可选择性取代的芳香性杂环族；或者R4表示H，R5如上所定义；或者R4和R5与它们连接的氮原子一起表示饱和的5到8个成员的杂环基团；R6为H，C1-3烷基基团，C1-3烷氧甲基基团，三氟甲基，羟基C1-3烷基基团，C1-3烷氧羰基，羧基，氰基，氨基甲酰基，一级或二级C1-3烷基甲酰基，乙酰基或化学式为-CONHNRaRb的肼基；但需注意的是，本发明还涉及制备这种化合物的方法，以及它们在肥胖、精神和神经疾病特别是肥胖的治疗中的应用方法和包含它们的制药组合物。
• 1,5-Diaryl-pyrrole-3-carboxamide derivatives and their use as cannabinoid receptor modulators
  申请人：Berggren Ingrid Kristina Anna

  公开号：US20060122230A1

  公开（公告）日：2006-06-08

  The present invention relates to a compound of formula (I) in which R 1 and R 2 independently represent phenyl, thienyl or pyridyl each of which is optionally substituted by one, two or three groups represented by Z; and R 3 is H, a C 1-3 alkyl group, a C 1-3 alkoxymethyl group, trifluoromethyl, a hydroxyC 1-3 alkyl group, an aminoC 1-3 alkyl group, C 1-3 alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C 1-3 alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula —CONHNR a R b wherein R a and R b are as defined for R 4 and R 5 respectively; X is CO or SO 2 ; Y is absent or represents NH optionally substituted by a C 1-3 alkyl group; R 4 and R 5 independently represent: a C 1-6 alkyl group; an (amino)C 1-4 alkyl-group in which the amino is optionally substituted by one or more C 1-3 alkyl groups; an optionally substituted non-aromatic C 3-15 carbocyclic group; a (C 3-12 cycloalkyl)C 1-3 alkyl-group; a group —(CH 2 ) r (phenyl) s ; naphthyl; anthracenyl; a saturated 5 to 8 membered heterocyclic group containing one nitrogen and optionally one of the following: oxygen, sulphur or an additional nitrogen wherein the heterocyclic group is optionally substituted; 1-adamantylmethyl; a group —(CH 2 ) t Het where Het represents an aromatic heterocycle optionally substituted; or R 4 represents H and R 5 is as defined above; or R 4 and R 5 together with the nitrogen atom to which they are attached represent a saturated 5 to 8 membered heterocyclic group; R 6 is H, a C 1-3 alkyl group, a C 1-3 alkoxymethyl group, trifluoromethyl, a hydroxyC 1-3 alkyl group, C 1-3 alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C 1-3 alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula —CONHNR a R b ; with provisos; to processes for preparing such compounds, to their use in the treatment of obesity, psychiatric and neurological disorders particularly obesity, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  本发明涉及一种化合物，其化学式为（I），其中R1和R2分别独立表示苯基，噻吩基或吡啶基，每个基团可选地被Z所代表的一个、两个或三个基团取代；而R3则表示H、C1-3烷基、C1-3烷氧甲基、三氟甲基、羟基C1-3烷基、氨基C1-3烷基、C1-3烷氧羰基、羧基、氰基、氨基甲酰基、一级或二级C1-3烷基甲酰基或肼基羰基，其中Ra和Rb分别如同R4和R5所定义；X为CO或SO2；Y为不存在或代表可选地被C1-3烷基取代的NH；而R4和R5独立地表示：C1-6烷基、（氨基）C1-4烷基，其中氨基可选地被一个或多个C1-3烷基取代，可选地被取代的非芳香性C3-15碳环基，（C3-12环烷基）C1-3烷基，基团—（CH2）r（苯基）s，萘基，蒽基，含有一个氮原子且可选地含有以下一种:氧、硫或另一个氮原子的饱和的5到8个成员杂环基，其中该杂环基可选地被取代；1-金刚烷甲基，基团—（CH2）tHet，其中Het代表可选地被取代的芳香性杂环；或者R4表示H，而R5如同上述所定义；或者R4和R5与它们所连接的氮原子一起表示一个饱和的5到8个成员杂环基；而R6表示H、C1-3烷基、C1-3烷氧甲基、三氟甲基、羟基C1-3烷基、C1-3烷氧羰基、羧基、氰基、氨基甲酰基、一级或二级C1-3烷基甲酰基或肼基羰基，其中Ra和Rb分别如同上述所定义；但需注意以下情况：本发明还涉及制备此类化合物的方法，以及将其用于治疗肥胖症、精神和神经疾病，特别是肥胖症的方法和含有它们的制药组合物。
• Aqueous dispersion comprising stable nanoparticles of a water-insoluble pyrrole carboxamide and excipient like middle chain triglycerides
  申请人：Lindfors Lennart

  公开号：US20060198893A1

  公开（公告）日：2006-09-07

  A process for the preparation of a stable dispersion of solid particles, in an aqueous medium comprising combining (a) a first solution comprising a substantially water-insoluble substance which is a pyrrole carboxamide compound of Formula I, a water-miscible organic solvent and an inhibitor with (b) an aqueous phase comprising water and optionally a stabiliser, thereby precipitating solid particles comprising the inhibitor and the substantially water-insoluble substance; and optionally removing the water-miscible organic solvent; wherein the inhibitor is a non-polymeric hydrophobic organic compound as defined in the description. Also claimed are stable dispersions prepared by the process, solid particles prepared by the process and use of such particles.

  一种制备稳定的固体颗粒分散液的方法，其中该分散液在水介质中，包括将（a）第一溶液与（b）水相结合，从而沉淀出包含抑制剂和基本上不溶于水的Formula I吡咯羧酰胺化合物的固体颗粒。第一溶液包括基本上不溶于水的物质、可溶于水的有机溶剂和抑制剂；水相包括水和可选的稳定剂；可选择去除可溶于水的有机溶剂；其中抑制剂是在描述中定义的非聚合疏水有机化合物。此外，还包括通过该方法制备的稳定分散液、通过该方法制备的固体颗粒以及使用这些颗粒的用途。
• Microwave-Assisted One-Pot Synthesis of N-Substituted 2-Methyl-1H-pyrrole-3-carboxylate Derivatives without Catalyst and Solvent
  作者：Bing Zhao、Wei Kan、Tao Jing、Xiao-hong Zhang、Yong-jie Zheng、Lin Chen

  DOI：10.3987/com-15-13340

  日期：——

  An efficient one-pot synthetic method for the N-substituted 2-methyl-1H-pyrrole-3-carboxylate derivatives has been accomplished via a microwave irradiation MCRs of various alpha-bromoacetophenone, amines, and ethyl acetoacetate without any solvent and catalyst. This approach provides a convenient one pot method for the synthesis of N-substituted 2-methyl-1H-pyrrole-3-carboxylate derivatives.
• 1,5-DIARYL-PYRROLE-3-CARBOXAMIDE DERIVATIVES AND THEIR USE AS CANNABINOID RECEPTOR MODULATORS
  申请人：AstraZeneca AB

  公开号：EP1578417A1

  公开（公告）日：2005-09-28