4-(3,4-二甲氧基苯基)丁酸甲酯 | 51686-49-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(3,4-二甲氧基苯基)丁酸甲酯
• 英文名称: methyl 4-(3,4-dimethoxyphenyl)butanoate
• 英文别名: γ-(3,4-Dimethoxy-phenyl)-buttersaeuremethylester；4-(3,4-Dimethoxyphenyl)buttersaeuremethylester
• CAS: 51686-49-8
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: FYXDSVDPYBFSOM-UHFFFAOYSA-N

物化性质

• 沸点：
  331.8±32.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3,4-二甲氧基苯基)丁酸甲酯 在 碳酸氢钠 、 一水合肼 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (7,8-dimethoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate
  参考文献：
  名称：

  Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles

  摘要：

  适当的芳基取代的不对称二羧肼化合物通过氧化从双肼酰胺生成，发生分子内环化，生成各种有用的杂环化合物，如N-取代的氧杂吲哚、羧基醇、苯并氮杂哌啶、苯并氮杂呋喃、苯并咪唑酮、苯并氧杂噁唑和吡唑酮，效率各不相同。文中描述了去除杂芳香化合物中N-酰基基团的方法。在弱酸性条件下，当存在相等机会进行ipso或正常环化时，前者过程优先发生。证据支持在ipso产物中发生C到C的迁移，用于形成甲氧基取代的羧基醇衍生物。显示出某个螺旋物质参与二烯酮–酚重排，以高产率生成相应的喹啉–酚。

  DOI：

  10.1039/b110414d
• 作为产物：
  描述：

  邻苯二甲醚 在 aluminum (III) chloride 、 四乙基硅烷 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 76.0h， 生成 4-(3,4-二甲氧基苯基)丁酸甲酯
  参考文献：
  名称：

  利用强亲电试剂合成中环大小的苯内酰胺，并定量评估环化反应速率对环大小的依赖性。

  摘要：

  通过氨基甲酰基阳离子（R1R2N +═C═O）的亲电芳族取代反应，无需稀释即可良好地获得高收率的苯甲酰胺。与五元或六元环形成相比，这些反应用于定量检测中型环形成的延迟程度。在25°C时，形成环苯并内酰胺的反应速率的顺序为六->五->七->八->九元环。本反应提供了八元和九元苯并内酰胺的途径。

  DOI：

  10.1021/acs.joc.9b02843

文献信息

• Pd-Catalyzed Regioselective Alkoxycarbonylation of 1-Alkenes Using a Lewis Acid [SnCl₂ or Ti(O^<i>i</i>Pr)₄] and a Phosphine
  作者：Manuel Amézquita-Valencia、George Achonduh、Howard Alper

  DOI：10.1021/acs.joc.5b00851

  日期：2015.6.19

  The phosphine ligand mediated palladium catalyzed alkoxycarbonylation of alkenes was investigated with the objective of attaining good linear selectivity for the ester. The effect of various parameters such as solvents, additives, palladium precursors, CO pressures, and alkenes of various structural complexities were examined. The results revealed the importance of using a Lewis acid such as SnCl2 or Ti(O'Pr)(4) in combination with a monodentate ligand such CYTOP 292 or P(p-anisy1)(3) to enhance the regioselectivity for the linear isomers in the range of 70-96%.
• Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD
  作者：Giuseppe Allegretta、Elisabeth Weidel、Martin Empting、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2014.11.055

  日期：2015.1

  A new strategy for treating Pseudomonas aeruginosa infections could be disrupting the Pseudomonas Quinolone Signal (PQS) quorum sensing (QS) system. The goal is to impair communication among the cells and, hence, reduce the expression of virulence factors and the formation of biofilms. PqsD is an essential enzyme for the synthesis of PQS and shares some features with chalcone synthase (CHS2), an enzyme expressed in Medicago sativa. Both proteins are quite similar concerning the size of the active site, the catalytic residues and the electrostatic surface potential at the entrance of the substrate tunnel. Hence, we evaluated selected substrates of the vegetable enzyme as potential inhibitors of the bacterial protein. This similarity-guided approach led to the identification of a new class of PqsD inhibitors having a catechol structure as an essential feature for activity, a saturated linker with two or more carbons and an ester moiety bearing bulky substituents. The developed compounds showed PqsD inhibition with IC50 values in the single-digit micromolar range. The binding mode of these compounds was investigated by Surface Plasmon Resonance (SPR) experiments revealing that their interaction with the protein is not influenced by the presence of the anthranilic acid bound to active site cysteine. Importantly, some compounds reduced the signal molecule production in cellulo. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Reaction of 2-butenoic acid dianion and its N-(4-methoxyphenyl)amide with methoxy-substituted arynes
  作者：Abdul Rakeeb Deshmukh、Tran Long、Edward R. Biehl

  DOI：10.1021/jo00028a049

  日期：1992.1

  N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide 9 (85-90%) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15%). Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amounts of 4-aryl-2-butenoic acids 15'. The exclusive low temperature (-30 to -40-degrees-C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures. The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.
• IRIE, HIROSHI;MARUYAMA, JUN;SHIMADA, MIKI;ZHANG, YONG;KOUNO, ISAO;SHIMAMO+, SYNLETT.,(1990) N, C. 421-423
  作者：IRIE, HIROSHI、MARUYAMA, JUN、SHIMADA, MIKI、ZHANG, YONG、KOUNO, ISAO、SHIMAMO+

  DOI：——

  日期：——