(+)-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 | 1414335-75-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-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
• 英文别名: (1S,2R,6S,7R,9R)-9-hydroxy-4-(4-methoxyphenyl)-9-methyl-11-propan-2-yl-6-thiophen-2-yltricyclo[5.2.2.02,6]undeca-4,10-diene-3,8-dione
• CAS: 1414335-75-3
• 化学式: C₂₆H₂₆O₄S
• 分子量: 434.556
• InChiKey: UOTXWMSSBZHEMR-WFPMDWFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-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 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以67%的产率得到(+)-9-hydroxy-4-(4-hydroxyphenyl)-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：

  对甲氧基苯乙酸乙酯 在 光气 、 aluminum (III) chloride 、 10% rhodium on carbon 、 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 、 均三甲苯 为溶剂， 反应 18.0h， 生成 (+)-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