(2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoic acid | 15542-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoic acid
• 英文别名: (E,E)-5-(4-methoxyphenyl)-2,4-pentadienoic acid；5-[p-Methoxyphenyl]-2,4-pentadienoic acid
• CAS: 15542-37-7
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: UODHHVJEXWSPFU-ZUVMSYQZSA-N

物化性质

• 熔点：
  179-180 °C
• 沸点：
  409.4±28.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 5-(4-Methoxy-phenyl)-penta-2,4-dienoic acid (1-methyl-4-pyridin-3-yl-butyl)-amide
  参考文献：
  名称：

  Pentadienyl carboxamide derivatives as antagonists of platelet activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl]-5,5-disubstituted-pentadienamides was prepared and evaluated for PAF-antagonist activity. Compounds were assayed in vitro in a PAF-binding assay employing washed, whole dog platelets as the receptor source and in vivo after intravenous or oral administration for their ability to prevent PAF-induced bronchoconstriction in guinea pigs. Criteria required for good oral activity in the latter model include an (E,-E)-5-phenyl-2,4-pentadienamide, a second phenyl or a four- or five-carbon alkyl moiety in the 5-position of the diene, and an (R)-[1-alkyl-4-(3-pyridinyl)butyl] substituent on the carboxamide nitrogen atom. The alkyl substituent on this side chain can be methyl, ethyl, or cyclopropyl. Two members of this series, [R-(E)]-5,5-bis(4-methoxy-phenyl)-N- [1-methyl-4-(3-pyridinyl)butyl]- 2,4-pentadienamide (31) and [R-(E,E)]-5-(4-methoxyphenyl)-N-[1-methyl-4- (3-pyridinyl)butyl]-2,4-decadienamide (58), were selected for further pharmacological evaluation. Both were found to be substantially longer acting after oral administration than the corresponding S enantiomers in the guinea pig bronchoconstriction assay. A second in vivo model used to evaluate PAF antagonists determines the ability of test compounds to decrease the area of skin wheals induced by an intradermal injection of PAF. In this model, using both rats and guinea pigs, compounds 31 and 58 were found to be as active as the reference PAF antagonist 3-[4-(2-chlorophenyl)-9-methyl-6H- 1-(4-morpholinyl)-1-propanone (45).

  DOI：

  10.1021/jm00128a026
• 作为产物：
  描述：

  4-甲氧基肉桂醛 生成 (2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoic acid
  参考文献：
  名称：

  Carbamic acid compounds comprising an amide linkage as hdac inhibitors

  摘要：

  这项发明涉及抑制HDAC活性的某些活性碳酸酰胺化合物，其化学式为（1），其中：A是芳基；Q1是至少有2个碳原子骨架的芳基前导基团；J是选择自以下的酰胺键：—NR1C(═O)—和—C(═O)NR1—；R1是酰胺取代基；Q2是酸前导基团；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这种化合物的药物组合物，以及在体外和体内使用这种化合物和组合物来抑制HDAC，例如，抑制增殖性疾病，如癌症和牛皮癣。

  公开号：

  US20040092598A1

文献信息

• Catalytic Hunsdiecker Reaction and One-Pot Catalytic Hunsdiecker–Heck Strategy: Synthesis of α,β-Unsaturated Aromatic Halides, α-(Dihalomethyl)benzenemethanols, 5-Aryl-2,4-pentadienoic acids, Dienoates and Dienamides
  作者：Dinabandhu Naskar、Sujit Roy

  DOI：10.1016/s0040-4020(99)01035-2

  日期：2000.3

  The reaction of α,β-unsaturated aromatic (or heteroaromatic) carboxylic acids with N-halosuccinimides (1 equiv.) and catalytic tetrabutylammonium trifluoroacetate (0.2 equiv.) in dichloroethane results in facile halodecarboxylation affording the corresponding (E)-halides in good to excellent yields. A similar reaction, but with 2 equiv. of N-halosuccinimides in acetonitrile-water (1:1 v/v) results

  α，β-不饱和芳族（或杂芳族）羧酸与N-卤代琥珀酰亚胺（1当量）和催化四丁基三氟乙酸铵（0.2当量）在二氯乙烷中的反应导致容易的卤代羧化，从而得到相应的（E）-卤化物优异的产量。类似的反应，但具有2当量。的N在乙腈-水中（1-1：1 v / v）中的-卤代琥珀酰亚胺导致相应的α-（二卤代甲基）苯甲醇的排他性形成。此外，已开发出一种结合了Hunsdiecker催化反应（在二氯乙烷中使用三氟乙酸四丁基铵）和Heck偶联（使用乙酸钯/三乙胺/三苯基锑/二氯乙烷）的一锅法，用于合成5-芳基-2,4-戊二烯酸，酯和酰胺，产率中等至良好。通过上述途径合成了天然产物胡椒碱和哌瓜胺。机理和理论研究（通过AM1计算）对当前的卤代羧化反应的机理提供了有用的见解，表明离子途径涉及卤离子跨碳-碳双键的攻击，
• [EN] TREATMENT OF DISORDERS ASSOCIATED WITH OXIDATIVE STRESS AND COMPOUNDS FOR SAME<br/>[FR] TRAITEMENT DE TROUBLES ASSOCIÉS AU STRESS OXYDATIF ET COMPOSÉS CORRESPONDANTS
  申请人：UNIV ADELAIDE

  公开号：WO2021179049A1

  公开（公告）日：2021-09-16

  The present invention relates to the treatment of disorders associated with oxidative stress including neuropathic pain and small synthetically derived compounds for treating such disorders.

  本发明涉及治疗与氧化应激相关的疾病，包括神经性疼痛以及用于治疗这些疾病的小型合成化合物。
• Occurrence of an Elongated <i>p</i>-Oxo Ketene Intermediate in the Dissociative Alkaline Hydrolysis of Aryl (2<i>E</i>,4<i>E</i>)-5-(4‘-Hydroxyphenyl)pentadienoates
  作者：Giorgio Cevasco、Daniele Vigo、Sergio Thea

  DOI：10.1021/jo0008439

  日期：2000.11.1

  The alkaline hydrolysis of title esters possessing acidic leaving groups follows an E1cB mechanism involving the participation of an "extra extended" p-oxo ketene intermediate. For the hydrolysis of the 2,4-dinitrophenyl ester kinetic data, activation parameters and trapping of the intermediate clearly indicate that the dissociative pathway carries the reaction flux. Break in the Bronsted plot of the

  具有酸性离去基团的标题酯的碱性水解遵循E1cB机理，该机理涉及“超扩展”对-氧代乙烯酮中间体的参与。对于2,4-二硝基苯基酯动力学数据的水解，活化参数和中间体的捕集清楚地表明，解离途径携带了反应通量。表观二阶速率常数与离去基团的pK（a）的布朗斯德图的破坏表明，对于pK（a）大于约6的酯，反应机理从E1cB变为B（Ac）2。
• Diamide compound and drugs containing the same
  申请人：Kowa Co., Ltd.

  公开号：US06340682B1

  公开（公告）日：2002-01-22

  The present invention provides diamide derivatives represented by the following general formula (1): wherein A is a phenyl group or the like, which may be substituted, B is —CH═CH—, —C═C—, —(CH═CH)2—, —C≡C—CH═CH—, —CH═CH—C≡C—, phenylene or the like, and W is or and medicines comprising such a compound. These compounds have an excellent inhibitory effect on the production of an IgE antibody and are hence useful as antiallergic agents and the like.

  本发明提供了以下一般式（1）所代表的二酰胺衍生物： 其中A是苯基或类似物，可以被取代，B是—CH═CH—，—C═C—，—(CH═CH)2—，—C≡C—CH═CH—，—CH═CH—C≡C—，苯基或类似物，W是 或 以及包含这种化合物的药物。这些化合物对IgE抗体的产生具有出色的抑制作用，因此可用作抗过敏药物等。
• Catalytic Regio- and Enantioselective Alkylation of Conjugated Dienyl Amides
  作者：Yafei Guo、Johanan Kootstra、Syuzanna R. Harutyunyan

  DOI：10.1002/anie.201808392

  日期：2018.10.8

  A method for catalytic asymmetric alkylation of conjugated dienyl amides has been developed and it allows efficient and high‐yielding transformations of a wide range of polyconjugated amides into the corresponding chiral products. Smooth addition of organomagnesium reagents to relatively unreactive dienyl amides with excellent 1,6‐ and 1,4‐selectivities, as well as enantioselectivites above 90 %, is

  已开发出一种共轭二烯基酰胺催化不对称烷基化的方法，该方法可以将各种范围的聚共轭酰胺高效高效地转化为相应的手性产物。由于路易斯酸和手性铜基催化剂的互补作用，可以将有机镁试剂平稳地添加到具有极好的1,6和1,4,4选择性以及相对于90％以上的对映体的相对无反应性的二烯基酰胺中。