(E)-3-ethoxy-1-(4-methoxylphenyl)prop-2-en-1-one | 143101-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-ethoxy-1-(4-methoxylphenyl)prop-2-en-1-one
• 英文别名: (E)-3-ethoxy-1-(4-methoxyphenyl)prop-2-en-1-one；(E)-3-ethoxy-1-(4-methoxy)phenylpropenone；3-Ethoxy-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 143101-59-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: ZIPYCDFHTDSPIZ-CMDGGOBGSA-N

物化性质

• 沸点：
  320.7±42.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-ethoxy-1-(4-methoxylphenyl)prop-2-en-1-one 在 sodium methylate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.25h， 生成 3-(4-甲氧基苯甲酰基)-1H-喹啉-4-酮
  参考文献：
  名称：

  A versatile and efficient synthesis of 3-aroyl-1,4-dihydroquinolin-4-ones

  摘要：

  A versatile and efficient method for preparation of 3-aroyl-4-quinolones is described. The procedure involved a Michael-type addition of methyl anthranylate with various beta-ketonic enol ethers followed by based promoted cyclisation. Different quinolones have been obtained. The ring closure is facilitated by heating at reflux in diphenyl ether leading to increase the rate of the cyclisation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.067
• 作为产物：
  描述：

  溴乙烷 、 对甲氧基苯乙酮 、 甲酸乙酯 在 sodium ethanolate 作用下， 以 乙醚 为溶剂， 反应 27.25h， 以62%的产率得到(E)-3-ethoxy-1-(4-methoxylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality

  摘要：

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.

  DOI：

  10.1021/jm070387h

文献信息

• Condensed Heteroaromatic Ring Systems. XX. Palladium-Catalyzed Carbonylative Coupling of Iodobenzenes with (Z)-1-Ethoxy-2-(tributylstannyl)ethene.
  作者：Takao SAKAMOTO、Akito YASUHARA、Yoshinori KONDO、Hiroshi YAMANAKA

  DOI：10.1248/cpb.40.1137

  日期：——

  Palladium-catalyzed cross-coupling reaction of iodobenzene and its 4-substituted derivatives, except for 4-nitroiodobenzene, with (Z)-1-ethoxy-2-(tributylstannyl)ethene under a carbon monoxide atmosphere (5 atm) gave the corresponding (E)-3-ethoxy-1-arylprop-2-en-1-ones in considerable yields. Syntheses of chromone and 4(1H)-quinolinone were accomplished by application of this method to 2-(methoxymethoxy)iodobenzene and ethyl 2-iodophenylcarbanylate, respectively. The results obtained on the carbonylative coupling reaction of halopyridines are also described.

  在碳氢化合物氛围（5个大气压）下，使用钯催化的偶联反应将碘苯及其4-取代衍生物（不包括4-硝基碘苯）与(Z)-1-乙氧基-2-(三丁基锡)乙烯反应，得到了相应的(E)-3-乙氧基-1-芳基丙-2-烯-1-酮，产率相当可观。通过将该方法应用于2-(美克锡基)碘苯和乙基2-碘苯基羧酸酯，分别合成了香豆素和4(1H)-喹啉酮。此外，还描述了卤吡啶的碳酰化耦合反应的结果。
• Selective Synthesis of α‐Alkoxy Enones by α‐Addition of Alcohols to Alkynones Using 1,1,1,3,3,3‐Hexafluoroisopropanol and PPh ₃ as Co‐catalysts
  作者：Xiu‐Ming Li、Jing‐Kui Yang

  DOI：10.1002/ejoc.202201163

  日期：2022.12.19

  The α-addition of alcohols to alkynones was demonstrated. A series of α-alkoxy enones can directly be synthesized in moderate to high yields under mild conditions. Mechanism studies were carried out by various means.

  证明了醇与炔酮的 α-加成。一系列α-烷氧基烯酮可以在温和条件下以中等到高产率直接合成。通过各种方式进行了机理研究。
• Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality
  作者：Eric Stern、Giulio G. Muccioli、Barbara Bosier、Laurie Hamtiaux、Régis Millet、Jacques H. Poupaert、Jean-Pierre Hénichart、Patrick Depreux、Jean-François Goossens、Didier M. Lambert

  DOI：10.1021/jm070387h

  日期：2007.11.1

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.
• A versatile and efficient synthesis of 3-aroyl-1,4-dihydroquinolin-4-ones
  作者：Eric Stern、Régis Millet、Patrick Depreux、Jean-Pierre Hénichart

  DOI：10.1016/j.tetlet.2004.10.067

  日期：2004.12

  A versatile and efficient method for preparation of 3-aroyl-4-quinolones is described. The procedure involved a Michael-type addition of methyl anthranylate with various beta-ketonic enol ethers followed by based promoted cyclisation. Different quinolones have been obtained. The ring closure is facilitated by heating at reflux in diphenyl ether leading to increase the rate of the cyclisation. (C) 2004 Elsevier Ltd. All rights reserved.