3-羟基-4-乙酰基苯硼酸频哪醇酯 | 1246560-24-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-羟基-4-乙酰基苯硼酸频哪醇酯
• 英文名称: 2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acetophenone
• 英文别名: 1-(2-Hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone；1-[2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone
• CAS: 1246560-24-6
• 化学式: C₁₄H₁₉BO₄
• 分子量: 262.113
• InChiKey: RILMKWXTPLJDAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-羟基-4-乙酰基苯硼酸频哪醇酯 、 (Z)-3,4,5-trimethoxy-β-iodostyrene 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 20.33h， 以56%的产率得到4-acetyl-3-hydroxy-3′,4′,5′-trimethoxy-(Z)-stilbene
  参考文献：
  名称：

  A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors

  摘要：

  A series of combretastatin derivatives were designed and synthesised by a two-step stereoselective synthesis by use of Wittig olefination followed by Suzuki cross-coupling. Interestingly, all new compounds (2a-2i) showed potent cell-based antiproliferative activities in nanomolar concentrations. Among the compounds, 2a, 2b and 2e were the most active across three cancer cell lines. In addition, these compounds inhibited the polymerisation of tubulin in vitro more efficiently than CA-4. They caused cell cycle arrest in G(2)/M phase further confirming their ability to inhibit tubulin polymerisation.

  DOI：

  10.1016/j.bmc.2020.115684
• 作为产物：
  描述：

  4-溴-2-羟基苯乙酮 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 以69%的产率得到3-羟基-4-乙酰基苯硼酸频哪醇酯
  参考文献：
  名称：

  A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors

  摘要：

  A series of combretastatin derivatives were designed and synthesised by a two-step stereoselective synthesis by use of Wittig olefination followed by Suzuki cross-coupling. Interestingly, all new compounds (2a-2i) showed potent cell-based antiproliferative activities in nanomolar concentrations. Among the compounds, 2a, 2b and 2e were the most active across three cancer cell lines. In addition, these compounds inhibited the polymerisation of tubulin in vitro more efficiently than CA-4. They caused cell cycle arrest in G(2)/M phase further confirming their ability to inhibit tubulin polymerisation.

  DOI：

  10.1016/j.bmc.2020.115684

文献信息

• A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors
  作者：Natalie G. Barnes、Anthony W. Parker、Amjed A. Ahmed Mal Ullah、Patricia A. Ragazzon、John A. Hadfield

  DOI：10.1016/j.bmc.2020.115684

  日期：2020.10

  A series of combretastatin derivatives were designed and synthesised by a two-step stereoselective synthesis by use of Wittig olefination followed by Suzuki cross-coupling. Interestingly, all new compounds (2a-2i) showed potent cell-based antiproliferative activities in nanomolar concentrations. Among the compounds, 2a, 2b and 2e were the most active across three cancer cell lines. In addition, these compounds inhibited the polymerisation of tubulin in vitro more efficiently than CA-4. They caused cell cycle arrest in G(2)/M phase further confirming their ability to inhibit tubulin polymerisation.