2-Phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4Hchromen-4-one | 955880-06-5

• 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: 2-Phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4Hchromen-4-one
• 英文别名: 6-pinacolatoborylflavone；2-Phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chromen-4-one；2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chromen-4-one
• CAS: 955880-06-5
• 化学式: C₂₁H₂₁BO₄
• 分子量: 348.206
• InChiKey: HJVWPXHHTBHMOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4Hchromen-4-one 、 6-溴-2-苯基-(4H)-4-苯并吡喃酮 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 苯 为溶剂， 反应 16.0h， 以67%的产率得到Biflavonyl-(6,6'')
  参考文献：
  名称：

  Efficient Synthesis of Biflavones Having A Ring-A Ring of Two Flavone Units Using Suzuki Cross-Coupling Reactions

  摘要：

  Biflavones having a A ring-A ring of two flavone units were easily prepared by using Suzuki cross-coupling reaction of borylated flavones with bromoflavones or flavone-5-triflate in good to excellent yields.

  DOI：

  10.3987/com-10-s(e)36
• 作为产物：
  描述：

  6-溴-2-苯基-(4H)-4-苯并吡喃酮 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以65%的产率得到2-Phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4Hchromen-4-one
  参考文献：
  名称：

  Inhibitory effect of synthetic C–C biflavones on various phospholipase A2s activity

  摘要：

  Several prototypes of C-C biflavones (a-f) were synthesized and evaluated their inhibitory activity against phospholipase A(2)s (PLA(2)s) activity. The synthetic C-C biflavones (a-f) showed rather different inhibitory activity against various PLA(2)s. Most synthetic C-C biflavonoids exhibited potent and broad inhibitory activity against various sPLA(2)s and cPLA(2) tested regardless of their structural array. In particular, of natural and synthetic biflavonoids tested, the synthetic C-C biflavonoid (d) only showed inhibitory activity against sPLA, X. None of the natural and synthetic biflavonoids tested showed inhibitory activity against sPLA, IB. Further chemical l modification of these basic structures will be carried out in order to investigate the synthetic C C biflavones which possess more selective inhibitory activity against isozymes of PLA(2) (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.07.054

文献信息

• Synthesis of Pinacol Arylboronates from Aromatic Amines: A Metal-Free Transformation
  作者：Di Qiu、Liang Jin、Zhitong Zheng、He Meng、Fanyang Mo、Xi Wang、Yan Zhang、Jianbo Wang

  DOI：10.1021/jo3018878

  日期：2013.3.1

  A metal-free borylation process based on Sandmeyer-type transformation using arylamines derivatives as the substrates has been developed. Through optimization of the reaction conditions, this novel conversion can be successfully applied to a wide range of aromatic amines, affording borylation products in moderate to good yields. Various functionalized arylboronates, which are difficult to access by

  基于芳基胺衍生物作为底物的基于Sandmeyer型转化的无金属硼化工艺已得到开发。通过优化反应条件，这种新颖的转化方法可以成功地应用于各种芳族胺，从而以中等至良好的收率获得硼酸酯化产物。通过这种无金属的转化，可以容易地获得各种难以通过其他方法获得的官能化的芳基硼酸酯。此外，在不纯化硼酸酯化产物的情况下，Suzuki-Miyaura交叉偶联后即可进行这种转化，从而增强了该方法的实用性。已经提出了可能的涉及自由基物质的反应机理。
• Inhibitory effect of synthetic C–C biflavones on various phospholipase A2s activity
  作者：Tae Chul Moon、Zhejiu Quan、Jeongsoo Kim、Hyun Pyo Kim、Ichiro Kudo、Makodo Murakami、Haeil Park、Hyeun Wook Chang

  DOI：10.1016/j.bmc.2007.07.054

  日期：2007.11

  Several prototypes of C-C biflavones (a-f) were synthesized and evaluated their inhibitory activity against phospholipase A(2)s (PLA(2)s) activity. The synthetic C-C biflavones (a-f) showed rather different inhibitory activity against various PLA(2)s. Most synthetic C-C biflavonoids exhibited potent and broad inhibitory activity against various sPLA(2)s and cPLA(2) tested regardless of their structural array. In particular, of natural and synthetic biflavonoids tested, the synthetic C-C biflavonoid (d) only showed inhibitory activity against sPLA, X. None of the natural and synthetic biflavonoids tested showed inhibitory activity against sPLA, IB. Further chemical l modification of these basic structures will be carried out in order to investigate the synthetic C C biflavones which possess more selective inhibitory activity against isozymes of PLA(2) (C) 2007 Published by Elsevier Ltd.
• Efficient Synthesis of Biflavones Having A Ring-A Ring of Two Flavone Units Using Suzuki Cross-Coupling Reactions
  作者：Hiroto Nakano、Yukio Hoshino、Haruo Matsuyama、Yoshihito Kohari

  DOI：10.3987/com-10-s(e)36

  日期：——

  Biflavones having a A ring-A ring of two flavone units were easily prepared by using Suzuki cross-coupling reaction of borylated flavones with bromoflavones or flavone-5-triflate in good to excellent yields.