3-carbethoxy-6-phenyl-4-pyrone | 134653-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-carbethoxy-6-phenyl-4-pyrone
• 英文别名: ethyl 4-oxo-6-phenyl-4H-pyran-3-carboxylate；3-carboethoxy-6-phenyl-4-pyrone；Ethyl 4-oxo-6-phenylpyran-3-carboxylate
• CAS: 134653-72-8
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: MSQIGRBBYOCUKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-carbethoxy-6-phenyl-4-pyrone 在 吡啶 、 tetraphosphorus decasulfide 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 1-pentyl-6-phenyl-4-thioxo-1,4-dihydropyridine-3-carboxylic acid
  参考文献：
  名称：

  4-Oxo-1,4-dihydropyridines as Selective CB₂ Cannabinoid Receptor Ligands: Structural Insights into the Design of a Novel Inverse Agonist Series

  摘要：

  Growing evidence shows that CB2 receptor is an attractive therapeutic target. Starting from a series of 4-oxo-1,4-dihydroquinoline-3-carboxamide as selective CB2 agonists, we describe here the medicinal chemistry approach leading to the development of CB2 receptor inverse agonists with a 4-oxo-1,4-dihydropyridine scaffold. The compounds reported here show high affinity and potency at the CB2, receptor while showing only modest affinity for the centrally expressed CB1 cannabinoid receptor. Further, we found that the functionality of this series is controlled by its C-6 substituent because agonists bear a methyl or a tert-butyl group and inverse agonists, a phenyl or 4-chlorophenyl group, respectively. Finally, in silico studies suggest that the C-6 substituent could modulate the conformation of W6.48 known to be critical in GPCR activation.

  DOI：

  10.1021/jm100286k
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.05h， 生成 3-carbethoxy-6-phenyl-4-pyrone
  参考文献：
  名称：

  Reappraising the Structures and Distribution of Metabolites from Black Aspergilli Containing Uncommon 2-Benzyl-4H-pyran-4-one and 2-Benzylpyridin-4(1H)-one Systems

  摘要：

  To date, natural products containing 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one substructures have been encountered in relatively few fungi outside of the black aspergilli clade. While exploring the occurrence of these compounds among Aspergillus spp., it was determined that the structures of the unusual furopyrrols tensidols A and B (5 and 6) and JBIR-86 and JBIR-87 (9 and 10) were incorrect and should be reassigned as 2-benzyl-4H-pyran-4-ones (7, 8, lie, and 12, respectively). The origin of the unique N-phenyl groups in the 2-benzylpyridin-4(1H)-ones nygerones A and B (1 and 2) were also examined, and it was established that N-phenylamides added to the culture medium were suitable substrates for generating these metabolites; however, this phenomenon remained limited to a single fungus in our collection (Aspergillus niger ATCC 1015). A variety of 2-benzyl-4H-pyran-4-ones and 2-benzylpyridin-4(1H)-ones were detected among the black aspergilli, but only pestalamide B (13) was found in all 11 of the tested strains. These metabolites, as well as a group of synthetic analogues, demonstrated weak antifungal activity against several Candida strains, Aspergillus flavus, and Aspergillus fumigatus.

  DOI：

  10.1021/np200454z

文献信息

• Silver(I)-Catalyzed Enantioselective [3+2]-Cycloaddition Reaction of α-Silylimines: A Facile Route to Quaternary-Carbon-Rich Scaffolds
  作者：Naredla Kesava-Reddy、Christopher Golz、Carsten Strohmann、Kamal Kumar

  DOI：10.1002/chem.201604793

  日期：2016.12.19

  A silver‐catalyzed highly enantioselective 1,3‐dipolar cycloaddition reaction of α‐silylimines with pyrone‐based trisubstituted olefins was developed affording bi‐ and tricyclic α‐quaternary‐carbon‐rich pyrano‐pyrrolidines in excellent yields. The tricyclic benzopyrone adducts thus obtained were efficiently transformed into highly complex tetracyclic scaffolds supporting four consecutive stereogenic

  已开发出一种银催化的α-甲硅烷基苯胺与吡喃基三取代烯烃的高对映选择性1,3-偶极环加成反应，从而以优异的收率提供了双环和三环的富含α-季碳的吡喃吡咯烷。由此获得的三环苯并吡喃酮加合物被有效地转化为高度复杂的四环支架，该支架支撑具有四个季碳的四个连续的立体异构中心。
• [EN] 1,4 DIHYDROPYRIDINE DERIVATIVES AND THEIR USES<br/>[FR] DÉRIVÉS DE LA 1,4-DIHYDROPYRIDINE ET LEURS UTILISATIONS
  申请人：UNIV LILLE II DROIT & SANTE

  公开号：WO2010133973A1

  公开（公告）日：2010-11-25

  The present invention relates to 1,4-dihydropyridine derivatives of the formula (I) and their uses in the treatment and/or prevention of diseases and disorders directly or indirectly associated with the modification (increase or decrease) of the activity of the cannabinoid receptor 2 (CB2).

  本发明涉及式(I)的1,4-二氢吡啶衍生物及其在治疗和/或预防与大麻素受体2（CB2）的活性修改（增加或减少）直接或间接相关的疾病和紊乱中的用途。
• Access to Chromenopyrrolidines Enabled by Organophotocatalyzed [2 + 2 + 1] Annulation of Chromones with <i>N</i>-Arylglycines
  作者：Xin Zhou、Biwei Zhang、Ping Wu、Wei Xu、Renqi Wang、Jingbai Li、Hongbin Zhai、Bin Cheng、Taimin Wang

  DOI：10.1021/acs.orglett.3c02801

  日期：2023.10.20

  conditions via organophotocatalyzed aerobic decarboxylative [2 + 2 + 1] annulation of chromones with N-arylglycines, in which N-arylglycines perform dual roles (i.e., radical precursor and methylene provider). Mechanistic studies suggested that a Giese-type radical addition and consequent Mannich pathway were likely responsible for the annulation reaction.

  在温和条件下，通过有机光催化色酮与N-芳基甘氨酸的需氧脱羧 [2 + 2 + 1] 环化，实现了色并吡咯烷的简便方法，其中N -芳基甘氨酸发挥双重作用（即自由基前体和亚甲基提供者）。机理研究表明吉斯型自由基加成和随后的曼尼希途径可能是环化反应的原因。
• 1,4-dihydropyridine derivatives and their uses
  申请人：Université de Lille 2 Droit et Santé

  公开号：EP2261211A1

  公开（公告）日：2010-12-15

  The present invention relates to 1,4-dihydropyridine derivatives of the formula (I) and their uses in the treatment and/or prevention of diseases and disorders directly or indirectly associated with the modification (increase or decrease) of the activity of the cannabinoid receptor 2 (CB2).

  本发明涉及式（I）的 1,4-二氢吡啶衍生物及其在治疗和/或预防与大麻素受体 2（CB2）活性改变（增加或降低）直接或间接相关的疾病和失调中的用途。
• Generation and in situ acylation of enaminone anions: a convenient synthesis of 3-carbethoxy-4(1H)-pyridinones and -4-pyrones and related compounds
  作者：Stuart W. McCombie、William A. Metz、Dennis Nazareno、Bandarpalle B. Shankar、Jayaram Tagat

  DOI：10.1021/jo00016a028

  日期：1991.8

  Treatment of 2-[(dimethylamino)methylene]-3-oxobutanoates 9 or 10 with LiN(SiMe3)2 in the presence of RCOCl results in C-acylation. The resulting intermediate, without isolation, may be converted to 6-R 3-Carbethoxy-4-pyrones (e.g., 12) by H3O+ or to the corresponding pyridinones (e.g., 13) by NH4OAc. Typically, yields are 55-75% for R groups lacking acidic alpha or gamma protons and ca. 30% for R = Me2CH or MeCH = CH. Replacing 9 with MeCOC(= CHNMe2)SCH2Ph (from MeCOCH2SCH2Ph and Me2NCH(OMe)2 similarly affords 3(PhCH2S)-substituted products such as 29. Alkylation of the pyridinone anions produces mixtures of N- and O-substituted compounds, with the latter predominating; aminolysis of the isolated pyrones (R'NH2-HOAc, where R' = alkyl, Ar, HO, etc.) is the preferred route to the 1-R'-substituted pyridinones.