3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one | 56492-64-9

• 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: 3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one
• 英文别名: 4-chloro-2'-hydroxy-4'-methoxychalcone；4-chloro-2'-hydroxy-4'methoxychalcone；2-Propen-1-one, 3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-；3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• CAS: 56492-64-9
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: PSHLSUYKYJMBFH-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102 °C(Solv: ethanol (64-17-5))
• 沸点：
  486.2±45.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one 在 silica supported double metal cyanide 作用下， 以 neat (no solvent) 为溶剂， 以85%的产率得到2-(4-chlorophenyl)-7-methoxychroman-4-one
  参考文献：
  名称：

  Silica supported-double metal cyanides (DMCs): A green and highly efficient catalytic protocol for isomerisation of 2′-hydroxychalcones to flavanones

  摘要：

  Four different double metal cyanides (NiHCFe, CrHCFe, MnHCFe and ZnHCFe) were synthesized, followed by adsorbed on silica gel and used as Lewis acid catalyst in the isomerisation of substituted 2'-hydroxychalcones to flavanones under solvent-free (dry) condition. Optimization of the reaction condition, temperature effects, DMC catalysts loading and re-useable catalytic activity were further studied during the reaction. Among these catalysts, NiHCFe at 35 mol% loading gave excellent yield (90%) at 100 degrees C temperature in 1.15 h. Catalyst (NiHCFe) easily recovered and re-used six times without much loss of its catalytic activity which gave 80-85% product yields each time. However, these DMCs were failed to give product in the solution phase even prolonging the reaction time at reflux temperature. Similarly, isomerization of substituted 2'-aminochalcones gave 2-5% yields either in solution phase or under solvent-free condition. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.03.009
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 36.0h， 生成 3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one
  参考文献：
  名称：

  新型苯并吡喃并[4,3- b ]苯并吡喃衍生物的合成及抗疟药评价

  摘要：

  发现7-甲氧基黄酮和5,7,8-三甲氧基黄酮经历了立体选择性酸催化的重排，以产生存在于天然产物依赖素中的苯并吡喃并[4,3- b ]苯并吡喃环系统。Dependensin及其类似物经过了针对恶性疟原虫的抗疟疾生长抑制测定，结果发现IC 50值在1.9和3.9μM之间。

  DOI：

  10.1016/j.bmc.2011.07.009

文献信息

• Synthesis, spectral characterization and catalytic studies of new ruthenium(II) chalcone thiosemicarbazone complexes
  作者：Manisekar Muthukumar、Periasamy Viswanathamurthi

  DOI：10.2478/s11532-009-0116-x

  日期：2010.2.1

  basis of data obtained, an octahedral structure was assigned for all of the complexes. The chalcone thiosemicarbazones behave as dianionic tridentate O, N, S donors and coordinate to ruthenium via the phenolic oxygen of chalcone, the imine nitrogen of thiosemicarbazone and thienol sulfur. The new complexes exhibit catalytic activity for the oxidation of primary and secondary alcohols to their corresponding

  一系列新的 [Ru(CO)(EPh3)(B)(L)] 型六配位钌 (II) 配合物（E = P 或 As；B = PPh3、AsPh3 或 Py；L = 查尔酮缩氨基硫脲） [RuHCl(CO)(EPh3)2(B)]（E = P 或 As；B = PPh3、AsPh3 或 Py）与查尔酮缩氨基硫脲在回流下在苯中反应制备。新配合物已通过分析和光谱（IR、UV-vis、1H、31P 和 13C NMR）方法进行表征。根据获得的数据，为所有配合物指定了八面体结构。查尔酮缩氨基硫脲作为双阴离子三齿 O、N、S 供体，并通过查耳酮的酚氧、缩氨基硫脲的亚胺氮和噻吩硫与钌配位。
• Ruthenium(II) carbonyl complexes containing chalconates and triphenylphosphine/arsine
  作者：P VISWANATHAMURTHI、M MUTHUKUMAR

  DOI：10.1007/s12039-011-0125-0

  日期：2011.9

  A series of new hexa-coordinated ruthenium(II) carbonyl complexes of the type [RuCl(CO)(EPh3)(B)(L1 − 4)] (4–15) (E = P or As; B = PPh3, AsPh3 or Py; L = 2′-hydroxychalcone) were synthesized from the reaction of [RuHCl(CO)(EPh3)2(B)] (1–3) (E = P or As; B = PPh3, AsPh3 or Py) with equimolar chalcone in benzene under reflux. The new complexes have been characterized by analytical and spectroscopic (IR

  [RuCl（CO）（EPh 3）（B）（L 1-4）]类型的一系列新的六配位钌（II）羰基络合物（4–15）（E = P或As； B = PPh 3，由[RuHCl（CO）（EPh 3）2（B）]（1-3）（E = P或As； B = PPh 3）反应合成了AsPh 3或Py； L = 2'-羟基查耳酮，AsPh 3或Py）与等摩尔查尔酮在苯中回流。新配合物的特征在于分析和光谱（IR，电子，1 H，31 P 1 H}和13NMR）方法。根据获得的数据，为所有配合物分配了八面体结构。在作为共氧化剂的N-甲基吗啉-N-氧化物（NMO）的存在下，该配合物具有将伯醇和仲醇氧化为相应的醛和酮的催化活性，也被发现是有效的转移加氢催化剂。配体及其配合物的抗真菌性能也已被检验，并与标准的Bavistin进行了比较。 合成并表征了稳定的钌（II）钌酸盐配合物。为所有配合物分配了八面体结构。发现新的络合物是有效的氧化和转移氢化催化剂。
• An efficient oxidative conversion of 2-aryl-2H-chromenes to the corresponding flavones by tert-butylhydroperoxide and copper bromide
  作者：Dipanwita Banerjee、Utpal Kayal、Gourhari Maiti

  DOI：10.1016/j.tetlet.2016.03.006

  日期：2016.4

  A simple and efficient method has been developed for the facile oxidation of chromenes to the corresponding flavones by tert-butylhydroperoxide (TBHP) in the presence of copper(II) bromide catalyst in toluene at 80 °C in a very short time. The reaction demonstrates excellent reactivity, functional group tolerance, and good to excellent yields without using conventional strong oxidizing agents.

  已经开发了一种简单有效的方法，用于在80℃下于很短时间内在甲苯中存在溴化铜（II）的情况下，通过叔丁基氢过氧化物（TBHP）轻松地将二甲基苯酮氧化为相应的黄酮。该反应显示出优异的反应性，官能团耐受性以及良好至优异的产率，而无需使用常规的强氧化剂。
• Simple and Efficient One Step Synthesis of Functionalized Flavanones and Chalcones
  作者：ABDULLAH SAAD ALBOGAMI、USAMA KARAMA、AHMED AMINE MOUSA、M. KHAN、SARA ABDULLAH AL-MAZROA、HAMAD Z. ALKHATHLAN

  DOI：10.13005/ojc/280201

  日期：2012.6.18

  A facile and highly efficient microwave-assisted synthesis of functionalized chalcones and flavanones based on the Claisen-Schmidt condensation reaction is reported. The method describes the synthesis of flavanones in single step with excellent yield and it was revealed that position and number of substituents on acetophenones and aromatic aldehydes played a very crucial and key role in the construction

  据报道，基于克莱森-施密特缩合反应，可以轻松，高效地通过微波辅助合成官能化的查耳酮和黄烷酮。该方法描述了一步合成黄烷酮的方法，收率很高，并且表明苯乙酮和芳族醛上取代基的位置和数量在黄烷酮衍生物的构建中起着至关重要的作用。在这32种合成化合物中，5个查耳酮和1个黄烷酮是新化合物。
• Certain 4-Iminoflavones Derivatives: Synthesis, Docking Studies, Antiasthmatic and Antimicrobial Agents
  作者：Shaila Khah、Rohit Goyal、Ankush Chabba、Varun Jaiswal、Gaurav Sharma、Mu. Naushad

  DOI：10.14233/ajchem.2016.19789

  日期：——

  considerably explored. In recent years, substituted synthetic flavonoids have been dragging continuous attention due to their broad range of biological activities. Flavonoids are very well know and documented to possess antioxidant effects, antiviral and leishmanicidal activity, Certain 4-Iminoflavones Derivatives: Synthesis, Docking Studies, Antiasthmatic and Antimicrobial Agents

  类黄酮是化合物的一组化学部分，其结构基于 C6-C3-C6，即两个苯环通过丙烷桥连接。黄酮类化合物是一类植物化合物，具有相似的黄酮骨架，由两个芳环和一个氧杂环组成 [1]。类黄酮可分为多种类别，即黄酮醇（槲皮素、山奈酚）、黄酮（木犀草素、芹菜素）、黄烷酮（橙皮素）、黄酮苷（芦丁）、黄酮木脂素（水飞蓟素）、黄烷（儿茶素、异黄酮苷） ）、花青素（花青素、飞燕草素）、金黄酮（leptosidin、aureusidin）、无色花青素（teracacidin）、新黄酮素（coutareagenin、dalbergin）、查耳酮[2]。所有类别的黄酮类化合物都表现出多种生物活性，但其中，对黄酮进行了大量研究。近年来，取代合成黄酮类化合物因其广泛的生物活性而受到持续关注。类黄酮是众所周知的，并被证明具有抗氧化作用、抗病毒和杀利什曼原虫活性、某些 4-亚氨基黄酮衍生物：合成、对接研究、抗哮喘和抗微生物剂