4-(3,5-dimethylphenoxy)-5-ethyl-6-methyl-3-vinyl-1H-pyridin-2-one | 929080-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3,5-dimethylphenoxy)-5-ethyl-6-methyl-3-vinyl-1H-pyridin-2-one
• 英文别名: 4-(3,5-dimethylphenoxy)-3-ethenyl-5-ethyl-6-methyl-1H-pyridin-2-one
• CAS: 929080-43-3
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: BDFLYDFJTMJIBC-UHFFFAOYSA-N

物化性质

• 熔点：
  208 °C
• 沸点：
  444.1±45.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3,5-dimethylphenoxy)-5-ethyl-6-methyl-3-vinyl-1H-pyridin-2-one 在 钯 氢气 、 SiO2 、 dichloromethane ethanol 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以to give the desired compound as colorless microcrystals (60 mg, 66%)的产率得到4-(3,5-dimethylphenoxy)-3,5-diethyl-6-methyl-1H-pyridin-2-one
  参考文献：
  名称：

  Pyridinone and pyridinethione derivatives having hiv inhibiting properties

  摘要：

  本发明涉及式(I)的化合物，其N-氧化物，药学上可接受的加成盐，季铵盐和立体化学异构体形式，其中Q是卤素，C1-6烷基或C2-6烯基; X为(a-2)，其中q和r为O，Z为O，S或SO; R1为芳基; R2选自甲酰基; C1-6烷氧羰基烷基; Het2; Het2C1-6烷基，C1-6烷基硫醚; C1-6烷基，可选用一个或两个取代基，独立地选自羟基和卤素; R3选自甲酰基; C1-6烷基，可选用一个或两个C1-6烷氧基; R1为氢，具有HTV抑制性能。

  公开号：

  US20040229847A1
• 作为产物：
  描述：

  5-ethyl-4-hydroxy-6-methylpyridin-2(1H)-one 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 13.5h， 生成 4-(3,5-dimethylphenoxy)-5-ethyl-6-methyl-3-vinyl-1H-pyridin-2-one
  参考文献：
  名称：

  Structure–activity relationship in the 3-iodo-4-phenoxypyridinone (IOPY) series: The nature of the C-3 substituent on anti-HIV activity

  摘要：

  As part of a systematic SAR study on the 3-iodo-4-phenoxypyridinone 3 (IOPY) type non-nucleoside reverse transcriptase inhibitors, the analogues 4a-4z bearing different C-3 substituents were synthesized and evaluated for their anti-HIV activity against wild-type HIV-1 and four of the principal HIV mutant strains (K103N, Y181C, Y188L, and 1100L). The results show that the 3-vinyl analogue 4j is the only compound which displays anti-HIV activity comparable to IOPY 3, and in this respect represents a possible back-up to this lead molecule. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.082

文献信息

• Pyridinone and pyridinethione derivatives having hiv inhibiting properties
  申请人：——

  公开号：US20040229847A1

  公开（公告）日：2004-11-18

  The present invention is concerned among others with compounds of formula (I), the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and stereochemically isomeric forms thereof, wherein Q is halo, C 1-6 alkyl or C 2-6 alkenyl; X is (a-2) with q and r being O and Z being O, S or SO; R 1 is aryl; R 2 is selected from formyl; C 1-6 alkyloxycarbonylalkyl; Het 2 ; Het 2 C 1-6 alkyl, C 1-6 alkylthio; C 1-6 alkyl optionally substituted with one or two substituents each independently selected from hydroxy, and halo; R 3 is selected from formyl; C 1-6 alkyl optionally substituted with one or two C 1-6 alkyloxy; R 1 is hydrogen, with HTV inhibiting properties. 1

  本发明涉及式(I)的化合物，其N-氧化物，药学上可接受的加成盐，季铵盐和立体化学异构体形式，其中Q是卤素，C1-6烷基或C2-6烯基; X为(a-2)，其中q和r为O，Z为O，S或SO; R1为芳基; R2选自甲酰基; C1-6烷氧羰基烷基; Het2; Het2C1-6烷基，C1-6烷基硫醚; C1-6烷基，可选用一个或两个取代基，独立地选自羟基和卤素; R3选自甲酰基; C1-6烷基，可选用一个或两个C1-6烷氧基; R1为氢，具有HTV抑制性能。
• PYRIDINONE AND PYRIDINETHIONE DERIVATIVES HAVING HIV INHIBITING PROPERTIES
  申请人：CENTRE NATIONAL DELA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：EP1318995A2

  公开（公告）日：2003-06-18
• US7115608B2
  申请人：——

  公开号：US7115608B2

  公开（公告）日：2006-10-03
• [EN] PYRIDINONE AND PYRIDINETHIONE DERIVATIVES HAVING HIV INHIBITING PROPERTIES<br/>[FR] DERIVES DE PYRIDINONE ET DE PYRIDINETHIONE PRESENTANT DES PROPRIETES INHIBITRICES DU VIH
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2002024650A2

  公开（公告）日：2002-03-28

  The present invention is concerned among others with compounds of formula (1), the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and stereochemically isomeric forms thereof, wherein Q is halo, C1-6 alkyl or C2-6 alkenyl; X is (a-2) with q and r being O and Z being O, S or SO; R1 is aryl; R2 is selected from formyl; C1-6alkyloxycarbonylalkyl; Het?2; Het2C¿1-6alkyl, C1-6alkylthio; C1-6alkyl optionally substituted with one or two substituents each independently selected from hydroxy, and halo; R3 is selected from formyl; C1-6alkyl optionally substituted with one or two C1-6alkyloxy; R4 is hydrogen, with HIV inhibiting properties.
• Structure–activity relationship in the 3-iodo-4-phenoxypyridinone (IOPY) series: The nature of the C-3 substituent on anti-HIV activity
  作者：Abdellah Benjahad、Said Oumouch、Jerôme Guillemont、Elisabeth Pasquier、Dominique Mabire、Koen Andries、Chi Hung Nguyen、David S. Grierson

  DOI：10.1016/j.bmcl.2006.10.082

  日期：2007.2

  As part of a systematic SAR study on the 3-iodo-4-phenoxypyridinone 3 (IOPY) type non-nucleoside reverse transcriptase inhibitors, the analogues 4a-4z bearing different C-3 substituents were synthesized and evaluated for their anti-HIV activity against wild-type HIV-1 and four of the principal HIV mutant strains (K103N, Y181C, Y188L, and 1100L). The results show that the 3-vinyl analogue 4j is the only compound which displays anti-HIV activity comparable to IOPY 3, and in this respect represents a possible back-up to this lead molecule. (c) 2006 Elsevier Ltd. All rights reserved.