(4-boronobenzyl)triphenylphosphonium bromide | 1247025-83-7

• 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: (4-boronobenzyl)triphenylphosphonium bromide
• CAS: 1247025-83-7
• 化学式: Br*C₂₅H₂₃BO₂P
• 分子量: 477.145
• InChiKey: UWJLMELEWYMROW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.14
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4-boronobenzyl)triphenylphosphonium bromide 以 乙腈 为溶剂， 生成 (E)-8-(diethylamino)-5-(4-(4-(dimethylamino)styryl)phenyl)-2-phenyl-3H,5H-5l4,12l4-benzo[5,6][1,3,2]oxazaborinino[2,3-b][1,3,4,2]oxadiazaborinin-3-one
  参考文献：
  名称：

  具有两个垂直ICT的硼酸衍生的水杨基hydr配合物的独特荧光：PET过程中的溶剂效应

  摘要：

  已经广泛观察到溶剂对有机化合物的吸收和发射光谱的影响。通常发现其带的位置，强度和形状通常被这些溶剂修饰。溶剂对分子内电荷转移（ICT）过程的影响已得到广泛报道，而溶剂对光致电子转移（PET）过程的影响却很少。在该贡献中，公开了具有两个垂直ICT状态的硼酸衍生的水杨基hydr复合物（BSs），BS-DPE和BS-DPBDE通过通过硼节点分离其两个ICT状态而开发了非荧光PET化合物。事实证明，在非氢键键合溶剂中的相对强酸性质子可激活PET的消失并恢复其荧光。

  DOI：

  10.1016/j.dyepig.2018.03.046
• 作为产物：
  描述：

  4-(溴甲基)苯硼酸 、 三苯基膦 以 乙腈 为溶剂， 反应 12.0h， 以95%的产率得到(4-boronobenzyl)triphenylphosphonium bromide
  参考文献：
  名称：

  具有两个垂直ICT的硼酸衍生的水杨基hydr配合物的独特荧光：PET过程中的溶剂效应

  摘要：

  已经广泛观察到溶剂对有机化合物的吸收和发射光谱的影响。通常发现其带的位置，强度和形状通常被这些溶剂修饰。溶剂对分子内电荷转移（ICT）过程的影响已得到广泛报道，而溶剂对光致电子转移（PET）过程的影响却很少。在该贡献中，公开了具有两个垂直ICT状态的硼酸衍生的水杨基hydr复合物（BSs），BS-DPE和BS-DPBDE通过通过硼节点分离其两个ICT状态而开发了非荧光PET化合物。事实证明，在非氢键键合溶剂中的相对强酸性质子可激活PET的消失并恢复其荧光。

  DOI：

  10.1016/j.dyepig.2018.03.046

文献信息

• Real-Time Mass Spectrometric Investigations into the Mechanism of the Suzuki–Miyaura Reaction
  作者：Lars P. E. Yunker、Zohrab Ahmadi、Jessamyn R. Logan、Wenzhao Wu、Tengfei Li、A. Martindale、Allen G. Oliver、J. Scott McIndoe

  DOI：10.1021/acs.organomet.8b00705

  日期：2018.11.26

  Real-time monitoring of the Suzuki–Miyaura reaction using mass spectrometry during sequential addition of the various reaction components suggests that a dynamic series of equilibria exist in these solutions. Depending on conditions, the boronic acid can be dehydrated, deprotonated, hydroxylated (or alkoxylated), or fluorinated. Palladium–phosphine species present include Pd(0) (to which the aryl iodide

  在依次添加各种反应组分的过程中，使用质谱对铃木-宫浦反应进行实时监控，表明这些溶液中存在动态平衡。取决于条件，硼酸可以被脱水，去质子化，羟基化（或烷氧基化）或氟化。存在的钯-膦物质包括Pd（0）（芳基碘迅速氧化添加到其中），Pd（II）芳基碘化物络合物，通过碘化物配体解离形成的阳离子Pd（II）物质和Pd（II ）双芳基配合物，最终通过还原消除将产物挤出。在催化条件下未观察到氟化或氢（烷-）氧基化的钯配合物。排除了几种重金属化组合作为反应性伙伴，但仍有几种可能性，
• 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
• Boronic acid derived salicylidenehydrazone complexes for wash-free fluorescence imaging of cellular organelles
  作者：Boyu Zhang、Gang Feng、Shichao Wang、Xuanjun Zhang

  DOI：10.1016/j.dyepig.2017.10.027

  日期：2018.2

  Wash-free fluorescence imaging process has intrinsic nature of monitoring biochemical process in real time fashion and enable us to get more insight on living organism. In this contribution, it was proved that boronic acid derived salicylidenehydrazone complexes (BSs) are suitable candidates for wash-free fluorescence labels. Through pre-installation of organelles' targeting group morpholine and triphenylphosphonium (TPP+) on phenyboronic acid and then assembly it with salicylidenehydrazone ligand by dehydration and dative N-B bond, Lyso-BS and Mito-BS were acquired, which were shown to selectively stain lysosomes and mitochondria with circumventing tedious wash-off procedures in Hela cells respectively, without inducing any appreciable cytotoxicity. Our findings indicate that BSs are potential candidates as wash-free fluorescent stains.