3a-(4-bromophenyl)-8b-hydroxy-6-methoxy-3-phenyl-2,3,3a,8b-tetrahydro-cyclopenta[b]benzofuran-1-one | 1228174-42-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3a-(4-bromophenyl)-8b-hydroxy-6-methoxy-3-phenyl-2,3,3a,8b-tetrahydro-cyclopenta[b]benzofuran-1-one
• CAS: 1228174-42-2
• 化学式: C₂₄H₁₉BrO₄
• 分子量: 451.316
• InChiKey: OZRBZKYXKYXWRP-OYDLWJJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3a-(4-bromophenyl)-8b-hydroxy-6-methoxy-3-phenyl-2,3,3a,8b-tetrahydro-cyclopenta[b]benzofuran-1-one 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以50%的产率得到(1R,3S,3aR,8bS)-3a-(4-bromophenyl)-6-methoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1,8b-diol
  参考文献：
  名称：

  Novel Flavaglines Displaying Improved Cytotoxicity

  摘要：

  Novel flavagline analogues were synthesized and examined with respect to their cytotoxicity Structural features critical to the potential of this class of anticancer natural products wet e unraveled We demonstrated, in particular, that the introduction of substituants at C-2 has a deleterious effect on multidrug resistance Replacement of the hydroxy at C-1 by an aminoformyl with the opposite configuration enhances the cytotoxicity and led to a compound that reduces tumors growth in an allograft model at nontoxic doses

  DOI：

  10.1021/jm101318b
• 作为产物：
  描述：

  2-(4-bromophenyl)-3-hydroxy-7-methoxy-4H-chromen-4-one 在 水 、 sodium methylate 、 lithium chloride 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.33h， 生成 3a-(4-bromophenyl)-8b-hydroxy-6-methoxy-3-phenyl-2,3,3a,8b-tetrahydro-cyclopenta[b]benzofuran-1-one
  参考文献：
  名称：

  Novel Flavaglines Displaying Improved Cytotoxicity

  摘要：

  Novel flavagline analogues were synthesized and examined with respect to their cytotoxicity Structural features critical to the potential of this class of anticancer natural products wet e unraveled We demonstrated, in particular, that the introduction of substituants at C-2 has a deleterious effect on multidrug resistance Replacement of the hydroxy at C-1 by an aminoformyl with the opposite configuration enhances the cytotoxicity and led to a compound that reduces tumors growth in an allograft model at nontoxic doses

  DOI：

  10.1021/jm101318b