5-(4-methoxyphenyl)-3-(thiophen-2-yl)cyclopent-2-en-1-one | 1414335-64-0

• 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)-3-(thiophen-2-yl)cyclopent-2-en-1-one
• CAS: 1414335-64-0
• 化学式: C₁₆H₁₄O₂S
• 分子量: 270.352
• InChiKey: RZJNVEZKAAECCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(4-methoxyphenyl)-3-(thiophen-2-yl)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 18.0h， 以60%的产率得到(+)-4-(4-methoxyphenyl)-9-hydroxy-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo[5.2.2.0^2,6]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：

  4-Chloro-2-(4-methoxyphenyl)pent-4-enoic acid 在 光气 、 aluminum (III) chloride 、 palladium diacetate 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 5-(4-methoxyphenyl)-3-(thiophen-2-yl)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