ethyl 2-ethoxycarbonyl-3-(4-methoxybenzoyl)butanoate | 539820-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-ethoxycarbonyl-3-(4-methoxybenzoyl)butanoate
• 英文别名: Diethyl 2-[1-(4-methoxyphenyl)-1-oxopropan-2-yl]propanedioate
• CAS: 539820-72-9
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: XKPYEXQDUFLMAS-UHFFFAOYSA-N

物化性质

• 熔点：
  155 °C(Solv: chloroform (67-66-3))
• 沸点：
  437.8±40.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-ethoxycarbonyl-3-(4-methoxybenzoyl)butanoate 在 盐酸 作用下， 反应 6.0h， 以81%的产率得到4-(4-methoxyphenyl)-3-methyl-4-oxobutyric acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of cis-Tetrahydrophthalazinone/Pyridazinone Hybrids:  A Novel Series of Potent Dual PDE3/PDE4 Inhibitory Agents

  摘要：

  In this study, the synthesis and in vitro and in vivo pharmacological investigations of a new series of phthalazinone/pyridazinone hybrids with both PDE3 and PDE4 inhibitory activities are described. These compounds combine the pharmacophores of recently discovered 4a,5,8,8a-tetrahydro-2H-phthalazin-1-one-type inhibitors of PDE4 and the well-known 2H-pyridazin-3-one-type PDE3 inhibitors such as the tetrahydrobenzimidazoles. Most of the synthesized compounds are pharmacologically spoken PDE3/PDE4 hybrids. All hybrids show potent PDE4 inhibitory activity (pIC(50) = 7.0-8.7), whereas the pIC(50) values for inhibition of PDE3 vary from 5.4 to 7.5. In general, analogues with a 5-methyl-4,5-dihydropyridazinone moiety exhibit the highest PDE3 inhibitory activities. The highest in vivo antiinflammatory activity is displayed by phthalazinones 43 and 44 showing, at a dose of 30 mumol/kg po, 46% inhibition of arachidonic acid (AA) induced mouse ear edema. No correlation was found between the in vitro PDE3 and/or PDE4 inhibitory activity and the in vivo antiinflammatory capacity after oral dosing.

  DOI：

  10.1021/jm030776l
• 作为产物：
  描述：

  对甲氧基苯丙酮 在 溴 、 sodium hydride 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 2-ethoxycarbonyl-3-(4-methoxybenzoyl)butanoate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of cis-Tetrahydrophthalazinone/Pyridazinone Hybrids:  A Novel Series of Potent Dual PDE3/PDE4 Inhibitory Agents

  摘要：

  In this study, the synthesis and in vitro and in vivo pharmacological investigations of a new series of phthalazinone/pyridazinone hybrids with both PDE3 and PDE4 inhibitory activities are described. These compounds combine the pharmacophores of recently discovered 4a,5,8,8a-tetrahydro-2H-phthalazin-1-one-type inhibitors of PDE4 and the well-known 2H-pyridazin-3-one-type PDE3 inhibitors such as the tetrahydrobenzimidazoles. Most of the synthesized compounds are pharmacologically spoken PDE3/PDE4 hybrids. All hybrids show potent PDE4 inhibitory activity (pIC(50) = 7.0-8.7), whereas the pIC(50) values for inhibition of PDE3 vary from 5.4 to 7.5. In general, analogues with a 5-methyl-4,5-dihydropyridazinone moiety exhibit the highest PDE3 inhibitory activities. The highest in vivo antiinflammatory activity is displayed by phthalazinones 43 and 44 showing, at a dose of 30 mumol/kg po, 46% inhibition of arachidonic acid (AA) induced mouse ear edema. No correlation was found between the in vitro PDE3 and/or PDE4 inhibitory activity and the in vivo antiinflammatory capacity after oral dosing.

  DOI：

  10.1021/jm030776l

文献信息

• Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: applications and mechanism thereof
  作者：Eduardo de Pedro Beato、Daniele Mazzarella、Matteo Balletti、Paolo Melchiorre

  DOI：10.1039/d0sc02313b

  日期：——

  detail a strategy that uses a commercially available nucleophilic organic catalyst to generate acyl and carbamoyl radicals upon activation of the corresponding chlorides and anhydrides via a nucleophilic acyl substitution path. The resulting nucleophilic radicals are then intercepted by a variety of electron-poor olefins in a Giese-type addition process. The chemistry requires low-energy photons (blue

  我们详细介绍了一种策略，该策略使用相应的氯化物和酸酐通过激活后，使用市售的亲核有机催化剂来生成酰基和氨基甲酰基基团。亲核酰基取代路径。然后，在Giese型加成过程中，所得的亲核基团被各种贫电子烯烃截获。化学过程需要低能光子（蓝色LED）来激活酰基和氨基甲酰基自由基前体，由于它们的高还原电位，因此不容易基于氧化还原的激活机制。为了阐明这种催化光化学自由基产生策略的关键机理，我们结合了瞬态吸收光谱研究，电化学研究，量子产率测量和关键中间体的表征。我们确定了各种非循环中间体，它们与反应性自由基进行光调节平衡。
• Synthesis and Structure−Activity Relationships of <i>cis</i>-Tetrahydrophthalazinone/Pyridazinone Hybrids:  A Novel Series of Potent Dual PDE3/PDE4 Inhibitory Agents
  作者：Margaretha Van der Mey、Kirsten M. Bommelé、Hildegard Boss、Armin Hatzelmann、Mike Van Slingerland、Geert J. Sterk、Hendrik Timmerman

  DOI：10.1021/jm030776l

  日期：2003.5.1

  In this study, the synthesis and in vitro and in vivo pharmacological investigations of a new series of phthalazinone/pyridazinone hybrids with both PDE3 and PDE4 inhibitory activities are described. These compounds combine the pharmacophores of recently discovered 4a,5,8,8a-tetrahydro-2H-phthalazin-1-one-type inhibitors of PDE4 and the well-known 2H-pyridazin-3-one-type PDE3 inhibitors such as the tetrahydrobenzimidazoles. Most of the synthesized compounds are pharmacologically spoken PDE3/PDE4 hybrids. All hybrids show potent PDE4 inhibitory activity (pIC(50) = 7.0-8.7), whereas the pIC(50) values for inhibition of PDE3 vary from 5.4 to 7.5. In general, analogues with a 5-methyl-4,5-dihydropyridazinone moiety exhibit the highest PDE3 inhibitory activities. The highest in vivo antiinflammatory activity is displayed by phthalazinones 43 and 44 showing, at a dose of 30 mumol/kg po, 46% inhibition of arachidonic acid (AA) induced mouse ear edema. No correlation was found between the in vitro PDE3 and/or PDE4 inhibitory activity and the in vivo antiinflammatory capacity after oral dosing.