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.
• Optimized Palladium(0)-catalyzed Suzuki Cross-coupling Reaction of Polystyrene-supported Selenenyl Flavanones: A Convenient Preparation of Biaryl-chromen-4-one
  作者：E Tang、Wen Li、Zhangyong Gao、Lianpeng Zhang、Qiushi Ma

  DOI：10.1002/cjoc.201280023

  日期：2012.3

  Application of the Suzuki cross‐coupling reaction for efficient synthesis of diverse substituted biaryl‐chromen‐4‐ones using an optimized palladium(0) catalyst system is reported. The coupling of arylboronic acids with the resin‐bound bromoflavanones which were prepared by organoselenium‐induced regioselective intramolecular cyclization of bromo‐2‐hydroxylchalcones proceeded smoothly. Biaryl‐chromen‐4‐ones

  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。
• 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.