4-trimethylsilylbiphenyl-4'-boronic acid | 711603-51-9

• 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-trimethylsilylbiphenyl-4'-boronic acid
• 英文别名: (4'-(Trimethylsilyl)-[1,1'-biphenyl]-4-yl)boronic acid；[4-(4-trimethylsilylphenyl)phenyl]boronic acid
• CAS: 711603-51-9
• 化学式: C₁₅H₁₉BO₂Si
• 分子量: 270.211
• InChiKey: PDGVMIWREJMDDL-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166.5 °C
• 沸点：
  407.2±55.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-trimethylsilylbiphenyl-4'-boronic acid 在 一氯化碘 、 三溴化硼 、 钯 作用下， 生成 4,2',5'-trihydroxy-4'''-iodo-[1,1',4',1'',4'',1''']-quaterphenyl
  参考文献：
  名称：

  Helical Nanofibers from Aqueous Self-Assembly of an Oligo(p-phenylene)-Based Molecular Dumbbell

  摘要：

  We have synthesized an amphiphilic dumbbell-shaped molecule consisting of dodeca-p-phenylene and aliphatic polyether dendrons as flexible end groups. The molecular dumbbell in aqueous solution self-assembles into well-defined left-handed helical cylinders with a diameter (8 nm) of a molecular length scale and a pitch length of 5.6 nm, as confirmed by TEM. These elementary helical fibrils are further assembled to give left-handed superhelical fibers with lengths up to several micrometers. Such a well-defined helical arrangement of conjugated rod building blocks may provide a new strategy for the design of one-dimensional nanostructured materials with biomimetic, electronic, and photonic functions.

  DOI：

  10.1021/ja051961m
• 作为产物：
  描述：

  (4'-bromo-[1,1'-biphenyl]-4-yl)trimethylsilane 在 正丁基锂 、 硼酸三甲酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.0h， 以5.20 g的产率得到4-trimethylsilylbiphenyl-4'-boronic acid
  参考文献：
  名称：

  Synthesis of pentadecaphenylenes, their inclusion properties, and nanostructure formation with C60

  摘要：

  通过相应的立普舒兹铜酸盐的电子转移氧化作用，合成了大环十五碳苯。十五碳苯在溶液中自我聚集形成凝胶。此外，它还在其空腔中加入了 C60，产生了一种纤维状包合物，在苯中显示出很强的凝胶能力。

  DOI：

  10.1039/c3cc42922a

文献信息

• Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates
  作者：Jin Xie、Kohei Sekine、Sina Witzel、Petra Krämer、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/anie.201806427

  日期：2018.12.17

  photochemical gold‐catalyzed chemo‐selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2‐ and sp3‐hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis

  Organoboron化合物是通用的合成构件。我们在此报告了一种新的策略，即光化学金催化的B，Si双功能化试剂与重氮盐的金化学选择性的Hiyama芳基化反应，该策略与常用策略正交，因此是合成有价值的联芳基硼酸酯的独特工具。通过这种新方法，获得了各种功能化的sp 2-和sp 3-杂交联芳基硼酸酯。值得注意的是，金催化与铜催化或钯催化的协同作用允许一锅式迭代C-X（杂原子）和C-C偶联，将几个简单的片段快速组装成相对复杂的分子。机理研究表明，无光敏剂的条件优于金/ Ru（bpy）3Cl 2双重催化。
• Reversible Transformation of Helical Coils and Straight Rods in Cylindrical Assembly of Elliptical Macrocycles
  作者：Jung-Keun Kim、Eunji Lee、Min-Cheol Kim、Eunji Sim、Myongsoo Lee

  DOI：10.1021/ja907462h

  日期：2009.12.16

  We have demonstrated that, as the molecular length of elliptical macrocycle is increased, the self-assembled structure changes from spherical micelles to helical coils and finally to monolayered vesicles, in the order of decreasing interfacial curvature. Notably, the helical coils reversibly transform into straight rods upon heating while maintaining the supramolecular chirality. This structural transition

  我们已经证明，随着椭圆大环分子长度的增加，自组装结构从球形胶束变成螺旋线圈，最后变成单层囊泡，按照界面曲率减小的顺序。值得注意的是，螺旋线圈在加热时可逆地转变为直杆，同时保持超分子手性。这种结构转变伴随着椭圆大环从船形构象到更平面构象的构象变化。
• 3-D Organic nanostructures from self-assembly of branched aromatic rods
  作者：Yong-Sik Yoo、Myongsoo Lee

  DOI：10.1039/b413205j

  日期：——

  Self-assembling molecules based on branched aromatic rods, which are prepared by repeating of aromatic coupling reaction and substitution, and flexible dibranched ether-type coils were synthesized. Aggregation behavior could be investigated by optical polarized microscopy, differential scanning calorimetry, and X-ray diffraction. In contrast to the molecule 1 which shows an isotropic liquid state, the more elongated molecules 2 and 3 are observed to organize into a 3-D primitive monoclinic lattice with three distinct nanoscale dimensions, in which rods are tilted with respect to the layer normal.

  通过重复芳香族偶联反应和取代反应，制备了基于支化芳香族棒的自组装分子，并合成了柔性双支化醚型线圈。聚合行为可通过偏振光学显微镜、差示扫描量热法和X射线衍射进行研究。与分子1呈现各向同性液态不同，更细长的分子2和3被观察到组织成三维原始单斜晶格，具有三个不同的纳米尺度，其中棒相对于层法线倾斜。
• Supramolecular Helical Columns from the Self-Assembly of Chiral Rods
  作者：Ja-Hyoung Ryu、Lijun Tang、Eunji Lee、Ho-Joong Kim、Myongsoo Lee

  DOI：10.1002/chem.200701080

  日期：2008.1.18

  chiral bridging group as a rigid segment and oligoether dendrons as flexible segments were synthesized and characterized. In the bulk state, both molecules self-assemble into a hexagonal columnar structure, as confirmed by X-ray scatterings and transmission electron microscopy (TEM) observations. Interestingly, these structures display opposite Cotton effects in the chromophore of the aromatic unit in

  合成和表征了由双（五-对亚苯基）共轭到开放或封闭的手性桥基作为刚性链段和寡醚树枝状分子作为柔性链段的手性桥杆分子（CBR）。如X射线散射和透射电子显微镜（TEM）观察所证实，在大分子状态下，两个分子都自组装成六方柱状结构。有趣的是，尽管手性桥基的手性相同，但这些结构在芳族单元的发色团上却显示出相反的棉花效应。通过光散射和TEM研究证实，该分子在水溶液中自组装成圆柱状胶束聚集体，并在圆二色性（CD）光谱中显示出强信号，表示单手螺旋构型。每个分子的CD光谱显示彼此相反的信号，与本体中的相似。值得注意的是，当将开放的CBR添加到封闭的CBR的溶液中直到一定浓度时，封闭的CBR的CD信号被放大。这意味着两个分子共同组装成单手螺旋结构，因为打开的手性桥具有构象柔性，该手性桥被反转以与封闭的CBR共同组装。这些结果表明，手性部分的小的结构修饰可以以相反的方式将手性信息转移至超分子组装体。当将开放的CB
• Highly Strained 1,8-Naphthalene-Bridged Cyclic Oligophenylenes and Their Open-Shell Diradical Dications
  作者：Chunchen Liu、Guangwu Li、Hoa Phan、Ya Zou、Xuefeng Lu、Jishan Wu

  DOI：10.1021/acs.orglett.1c01595

  日期：2021.6.18

  The synthesis and characterization of two 1,8-naphthalene-bridged cyclic oligo-para-phenylenes with four or eight phenylene units are reported. Both molecules exhibit a highly strained structure with two nearly face-to-face arranged p,p′-biphenylylene/p,p′-quaterphenylylene chains. Their dications were obtained by chemical oxidation with NO·SbF6, and both showed open-shell singlet diradical character

  报道了两个具有四个或八个亚苯基单元的1,8-萘桥连环状低聚对亚苯基的合成和表征。两种分子都表现出高度应变的结构，具有两个几乎面对面排列的p , p '-亚联苯/ p , p '-四亚联苯链。它们的标记是通过用 NO·SbF 6化学氧化获得的，两者都显示开壳单线态双自由基特征，具有小的单线态-三线态能隙。