(3-boronobenzyl)triphenylphosphonium bromide | 1247025-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-boronobenzyl)triphenylphosphonium bromide
• 英文别名: [(3-Boronophenyl)methyl]triphenyl-phosphonium,monobromide；(3-boronophenyl)methyl-triphenylphosphanium;bromide
• CAS: 1247025-84-8
• 化学式: Br*C₂₅H₂₃BO₂P
• 分子量: 477.145
• InChiKey: VDNRROALFUZCBO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.14
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴甲基苯硼酸 、 三苯基膦 以 乙腈 为溶剂， 反应 12.0h， 以83%的产率得到(3-boronobenzyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Boronated phosphonium salts containing arylboronic acid, closo-carborane, or nido-carborane: synthesis, X-ray diffraction, in vitro cytotoxicity, and cellular uptake

  摘要：

  The preparation of boronated triaryl and tetraaryl phosphonium salts of the type [PPh3CH2R]Br [R is 4-boronophenyl (1), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)phenyl (2), 3-boronophenyl (3), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)phenyl (4), 2-boronophenyl (5), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)phenyl (6), and closo-1,2-carboran-1-yl (7)] is described These compounds were prepared by the reaction of triphenyl-phosphine with benzylic bromides or 1-bromomethyl-closo-1, 2-carborane in acetonitrile solution at 85 C The zwitter-ionic nido-7,8-carborane derivative PPh3CH2C2B9H11 (8) was prepared by treatment of 7 with cesium fluoride in refluxing ethanol All compounds were fully characterized by multinuclear (H-1, B-11, C-13, and P-31) 1D- and 2D-NMR spectroscopy, electrospray ionization mass spectrometry, and elemental analysis, and single-crystal X-ray structures were determined for compounds 1, 3, 7, and 8 The cytotoxicities and boron uptake of selected derivatives were investigated in vitro using human glioblastoma (T98G) and canine kidney tubule (MDCK II) cells The zwitterionic species 8 was found to be the least cytotoxic agent while also delivering the greatest amount of boron to the T98G cells, peaking at 9 15 +/- 2 65 mu g B/mg protein

  DOI：

  10.1007/s00775-010-0690-6

文献信息

• Boronated phosphonium salts containing arylboronic acid, closo-carborane, or nido-carborane: synthesis, X-ray diffraction, in vitro cytotoxicity, and cellular uptake
  作者：Daniel E. Morrison、Fatiah Issa、Mohan Bhadbhade、Ludwig Groebler、Paul K. Witting、Michael Kassiou、Peter J. Rutledge、Louis M. Rendina

  DOI：10.1007/s00775-010-0690-6

  日期：2010.11

  The preparation of boronated triaryl and tetraaryl phosphonium salts of the type [PPh3CH2R]Br [R is 4-boronophenyl (1), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)phenyl (2), 3-boronophenyl (3), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)phenyl (4), 2-boronophenyl (5), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)phenyl (6), and closo-1,2-carboran-1-yl (7)] is described These compounds were prepared by the reaction of triphenyl-phosphine with benzylic bromides or 1-bromomethyl-closo-1, 2-carborane in acetonitrile solution at 85 C The zwitter-ionic nido-7,8-carborane derivative PPh3CH2C2B9H11 (8) was prepared by treatment of 7 with cesium fluoride in refluxing ethanol All compounds were fully characterized by multinuclear (H-1, B-11, C-13, and P-31) 1D- and 2D-NMR spectroscopy, electrospray ionization mass spectrometry, and elemental analysis, and single-crystal X-ray structures were determined for compounds 1, 3, 7, and 8 The cytotoxicities and boron uptake of selected derivatives were investigated in vitro using human glioblastoma (T98G) and canine kidney tubule (MDCK II) cells The zwitterionic species 8 was found to be the least cytotoxic agent while also delivering the greatest amount of boron to the T98G cells, peaking at 9 15 +/- 2 65 mu g B/mg protein