3,5-bis(4-methoxyphenyl)cyclopent-2-en-1-one | 1414335-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(4-methoxyphenyl)cyclopent-2-en-1-one
• CAS: 1414335-62-8
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: DSJXGQWVYNTWKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,5-bis(4-methoxyphenyl)cyclopent-2-en-1-one 、 3,10-dihydroxy-6,12-di-iso-propyl-3,10-dimethyltricyclo[6.2.2.0^2,7]dodeca-5,11-diene-4,9-dione 在 10% rhodium on carbon 作用下， 以 均三甲苯 为溶剂， 反应 12.0h， 以75%的产率得到(1S,2R,6S,7R,9R)-9-hydroxy-4,6-bis(4-methoxyphenyl)-9-methyl-11-propan-2-yltricyclo[5.2.2.02,6]undeca-4,10-diene-3,8-dione
  参考文献：
  名称：

  Synthesis of Chamaecypanone C Analogues from in Situ-Generated Cyclopentadienones and Their Biological Evaluation

  摘要：

  A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure.

  DOI：

  10.1021/ja3084708
• 作为产物：
  描述：

  对甲氧基苯乙酸乙酯 在 光气 、 aluminum (III) chloride 、 水 、 palladium diacetate 、 sodium hexamethyldisilazane 、 potassium carbonate 、 sodium hydroxide 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 3,5-bis(4-methoxyphenyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  Synthesis of Chamaecypanone C Analogues from in Situ-Generated Cyclopentadienones and Their Biological Evaluation

  摘要：

  A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure.

  DOI：

  10.1021/ja3084708

文献信息

• Supported Rhodium Nanoparticle-Catalyzed Intermolecular Regioselective Carbonylative Cyclization of Terminal Alkynes using Oxalic Acid as Sustainable C₁Source
  作者：Nitul Ranjan Guha、Vandna Thakur、Dhananjay Bhattacherjee、Richa Bharti、Pralay Das

  DOI：10.1002/adsc.201600451

  日期：2016.12.7

  Polystyrene‐supported rhodium(0) (Rh@PS) nanoparticles (NPs) as a heterogeneous catalyst have been used for the synthesis of monocyclic 3,5‐disubstituted cyclopent‐2‐enones from terminal alkynes and oxalic acid as the in situ C1 source following an intermolecular [2+2+1]–reductive carbonylative cyclization (RCC) reaction. Oxalic acid in the presence of Rh@PS catalyst plays a dual role by acting as CO source

  聚苯乙烯负载的铑（0）（Rh @ PS）纳米颗粒（NPS）作为非均相催化剂已用于由末端炔烃和草酸作为原位C 1合成单环3,5-二取代的环戊-2-烯酮分子间[2 + 2 + 1]-还原羰基化环化（RCC）反应后产生。草酸在Rh @ PS催化剂的存在下起着双重作用，它起着CO源和还原剂（H 2）的作用，使该方法可用于所需的产物合成。草酸与Rh @ PS的PS表面的离子相互作用有助于维持与产物形成所需的底物和催化剂的紧密邻近并富有成果。