(E)-1-phenyl-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-phenyl-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(3,5-dimethoxyphenyl)-1-phenylprop-2-en-1-one
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: WAUNLZDTSDIAKQ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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)-1-phenyl-3-(3,4-dimethoxyphenyl)prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-(3,4-dimethoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Development of 5-(Aryl)-3-phenyl-1H-pyrazole Derivatives as Potent Antimicrobial Compounds

  摘要：

  通过克莱森-施密特冷凝反应，合成了一系列16种查尔酮化合物，使用不同的醛与乙酰苯酮在氢氧化钾的碱性条件下于乙醇中发生反应。反应获得期望产物，产率良好。随后，所有16种化合物通过在回流条件下用水合肼处理转化为吡唑。对查尔酮和吡唑进行了体外抗菌（大肠杆菌、金黄色葡萄球菌和铜绿假单胞菌）和抗真菌（青霉菌、角质毛霉和白色念珠菌）活性筛选。这些化合物的生物活性与市售抗生素氨苄青霉素和抗真菌剂米康唑进行了比较。研究发现，吡唑在抗微生物活性方面比对应的查尔酮更为活跃和有效。在测试的7种吡唑化合物中，4h、4j、4l、4m和4n五种化合物表现出很强的抗微生物活性。因此，这些衍生物有望成为进一步开发的极具潜力的分子。

  DOI：

  10.14233/ajchem.2019.21455
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 苯乙酮 在 alkali hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (E)-1-phenyl-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Development of 5-(Aryl)-3-phenyl-1H-pyrazole Derivatives as Potent Antimicrobial Compounds

  摘要：

  通过克莱森-施密特冷凝反应，合成了一系列16种查尔酮化合物，使用不同的醛与乙酰苯酮在氢氧化钾的碱性条件下于乙醇中发生反应。反应获得期望产物，产率良好。随后，所有16种化合物通过在回流条件下用水合肼处理转化为吡唑。对查尔酮和吡唑进行了体外抗菌（大肠杆菌、金黄色葡萄球菌和铜绿假单胞菌）和抗真菌（青霉菌、角质毛霉和白色念珠菌）活性筛选。这些化合物的生物活性与市售抗生素氨苄青霉素和抗真菌剂米康唑进行了比较。研究发现，吡唑在抗微生物活性方面比对应的查尔酮更为活跃和有效。在测试的7种吡唑化合物中，4h、4j、4l、4m和4n五种化合物表现出很强的抗微生物活性。因此，这些衍生物有望成为进一步开发的极具潜力的分子。

  DOI：

  10.14233/ajchem.2019.21455

文献信息

• .omega.-[(4,6-Diphenyl-2-pyridyl)oxy]alkanoic acid derivatives: a new family of potent and orally active LTB4 antagonists
  作者：Richard Labaudiniere、Norbert Dereu、Francoise Cavy、Marie Christine Guillet、Olivier Marquis、Bernard Terlain

  DOI：10.1021/jm00101a008

  日期：1992.11

  A series of omega-[(4,6-diphenyl-2-pyridyl)oxy]alkanoic acid derivatives was prepared which inhibited the binding of leukotriene B4 to its receptors on guinea pig spleen membranes and on human polymorphonuclear leukocytes (PMNs) and selectively antagonized the LTB4-induced elastase release in human PMNs. On the basis of these three screens, a structure-activity relationship was investigated. Alpha-Substitution on the carboxylic acid side chain led to only small changes in the binding affinities but greatly enhanced the LTB4 antagonist activity. Substitution on the phenyl rings was also evaluated. The terminal carboxylic acid function can be replaced by a tetrazole ring without loss in activity. The beat in vitro LTB4 antagonists of this series were investigated in vivo in the inhibition of LTB4-induced leukopenia in rabbits. Compound 9b (RP69698) displayed potent LTB4 antagonist activity, after oral administration, with an ED50 value of 6.7 mg/kg.
• Speedy and Regioselective 1,2-Reduction of Conjugated α,β-Unsaturated Aldehydes and Ketones Using NaBH₄/I₂
  作者：Jasvinder Singh、Irvinder Kaur、Jasamrit Kaur、Aman Bhalla、Goverdhan L. Kad

  DOI：10.1081/scc-120015699

  日期：2003.3

  Synthesis of allylic alcohols from alpha,beta-unsaturated aldehydes/ketones has been achieved in excellent yields utilizing NaBH4 and iodine. This reducing agent is mild and tolerant to a number of functional groups.
• Labaudiniere Richard, Dereu Norbert, Cavy Francoise, Guillet Marie-Christ+, J. Med. Chem., 35 (1992) N 23, S 4315-4324
  作者：Labaudiniere Richard, Dereu Norbert, Cavy Francoise, Guillet Marie-Christ+

  DOI：——

  日期：——
• Kinetic and Mechanistic Studies of the Selective Hydrogenation of ( <i>E</i> )‐Chalcones in Biomass‐Derived γ‐Valerolactone Catalyzed by Rh−PPh ₃ Complexes
  作者：Imre Tóth、József M. Tukacs、László T. Mika

  DOI：10.1002/cctc.202201480

  日期：——

  Abstractγ‐Valerolactone as a renewable, polar aprotic solvent was evaluated in the selective hydrogenation of carbon‐carbon double bond of chalcones from both catalytic and mechanistic aspects. By using triphenylphosphine‐modified cationic rhodium catalyst systems reasonably high activities (TOFinitial∼1200 h−1) were achieved in the selective hydrogenation of (E)‐chalcone (CHL), as a common model substrate for α,β‐unsaturated ketones, to dihydrochalcone (DHC). Various derivatives of CHL, which were substituted on the styryl phenyl groups also showed exclusive selectivity for the hydrogenation of the C=C double bond. The optimal PPh3/Rh ratio was between 2.5 to 3, but higher ratios were advantageously also tolerated, which is beneficial for the process chemistry. The solvent GVL proved to stable enough under the reaction conditions for waste‐free recycling. Kinetic studies and NMR spectra from the analogous deuteration of chalcone by using the cationic Rh‐PPh3 system clearly show the olefin insertion as the rate‐determining step with definite irreversibility. By investigating the substituent effect on the phenyl ring of the styryl moiety of chalcone, a quasi‐linear correlation was found between the electronic parameters of the para‐substituents and the activity with electron donor groups being favorable for the reaction rate. In summary, an environmentally friendly and feasible method is presented for the production of valuable DHC intermediates in view of their pharmaceutical importance.
• US5366982A
  申请人：——

  公开号：US5366982A

  公开（公告）日：1994-11-22