2-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-chromen-4-one | 955880-08-7

• 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-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-chromen-4-one
• 英文别名: 2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]chromen-4-one；2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]chromen-4-one
• CAS: 955880-08-7
• 化学式: C₂₁H₂₁BO₄
• 分子量: 348.206
• InChiKey: ACRWOPIYSUZCKM-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-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-chromen-4-one 、 4-bromo-2'-hydroxylchalcone 在 zinc(II) chloride 、 四(三苯基膦)钯 、 sodium hydroxide 、 双氧水 作用下， 以 二氯甲烷 、 乙二醇二甲醚 、 四氢呋喃 、 水 为溶剂， 反应 29.0h， 以40%的产率得到4',4'''-biflavone
  参考文献：
  名称：

  优化的钯（0）催化的聚苯乙烯负载硒基黄酮类化合物的Suzuki交叉偶联反应：联芳基-铬-4-酮的便捷制备

  摘要：

  据报道，使用优化的钯（0）催化剂体系，Suzuki交叉偶联反应在高效合成各种取代的联芳基-铬--4-酮中的应用。芳基硼酸与树脂键合的溴代黄酮的偶联反应顺利进行，该反应是通过有机硒诱导的溴代-2-羟甲基卤代烷的区域选择性分子内环化反应而进行的。联芳基-苯并吡喃-4-酮是由随后的氧化硒合成顺良好总产量在剔除。

  DOI：

  10.1002/cjoc.201280023
• 作为产物：
  描述：

  4-溴黄酮 、 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84%的产率得到2-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-chromen-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

• METHOD FOR HIGH-SPEED FLUOROMETHYLATION AND PROCESS FOR PREPARATION OF PET TRACER USING SAME
  申请人：Riken

  公开号：EP2508505B1

  公开（公告）日：2014-10-08
• Synthesis of phospholipase A2 inhibitory biflavonoids
  作者：Jianjun Chen、Hyeun Wook Chang、Hyun Pyo Kim、Haeil Park

  DOI：10.1016/j.bmcl.2006.01.117

  日期：2006.5

  A series of C-C biflavones was designed to investigate the relationship between structural array of different flavone-flavone subunit linkage and the inhibitory activity against phospholipase A(2) (PLA(2)). Among six classes of C-C biflavones designed, four classes of C-C biflavones, which have flavone-flavone subunit linkages at A ring-A ring, A ring-B ring, B ring-B ring, and B ring-C ring, were synthesized. The synthetic biflavones exhibited somewhat different inhibitory activities against sPLA(2)-IIA. Among them, the biflavone a having a C-C 4'-4' linkage showed comparable inhibitory activity with that of the natural biflavonoid, ochnaflavone, and 7-fold stronger activity than that of amentoflavone. Further chemical modification is being carried out in order to obtain the chemically optimized biflavonoids. (C) 2006 Elsevier Ltd. All rights reserved.