5-(4-Methoxyphenyl)cyclopent-2-en-1-one | 1414335-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-Methoxyphenyl)cyclopent-2-en-1-one
• 英文别名: 5-(4-methoxyphenyl)cyclopent-2-en-1-one
• CAS: 1414335-50-4
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: QUKDUZFNVWADBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-(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45%的产率得到8-hydroxy-4-(4-methoxyphenyl)-8-methyl-10-(propan-2-yl)-tricyclo[5.2.2.0^2,6]undeca-4,10-diene-3,9-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：

  4-Chloro-2-(4-methoxyphenyl)pent-4-enoic acid 在 光气 、 aluminum (III) chloride 、 氯化铵 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 5-(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

• [EN] CYCLOPENTENONES DERIVATIVES AND THEIR USE AS ANTIBIOTICS<br/>[FR] DÉRIVÉS DE CYCLOPENTÉNONES ET LEUR UTILISATION EN TANT QU'ANTIBIOTIQUES
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2022122975A1

  公开（公告）日：2022-06-16

  The present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt and/or solvate thereof, for use as a drug, especially as an antibiotic. The present invention also relates to a pharmaceutical composition comprising said compound of formula (I) and at least one pharmaceutically acceptable excipient. The present invention further concerns a method of preparation of a compound of formula (I').

  本发明涉及公式(I)化合物或其药学上可接受的盐和/或溶剂，用作药物，特别是抗生素。本发明还涉及一种包含公式(I)化合物和至少一种药学上可接受的辅料的制药组合物。本发明还涉及一种制备公式(I')化合物的方法。
• Synthesis of Chamaecypanone C Analogues from <i>in Situ</i>-Generated Cyclopentadienones and Their Biological Evaluation
  作者：Suwei Dong、Tian Qin、Ernest Hamel、John A. Beutler、John A. Porco

  DOI：10.1021/ja3084708

  日期：2012.12.5

  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.