4,4'-bis(ethoxy dimethyl silyl)biphenyl | 201603-69-2

• 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: 4,4'-bis(ethoxy dimethyl silyl)biphenyl
• 英文别名: 4,4'-Bis(dimethylethoxysilyl)biphenyl；ethoxy-[4-[4-[ethoxy(dimethyl)silyl]phenyl]phenyl]-dimethylsilane
• CAS: 201603-69-2
• 化学式: C₂₀H₃₀O₂Si₂
• 分子量: 358.628
• InChiKey: WBXHBWCRAYPDEY-UHFFFAOYSA-N

物化性质

• 沸点：
  168-169°C / 0.1
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-bis(ethoxy dimethyl silyl)biphenyl 在 正丁基锂 、 乙酰氯 作用下， 反应 6.5h， 生成 [4-[4-[Dimethyl(prop-1-ynyl)silyl]phenyl]phenyl]-dimethyl-prop-1-ynylsilane
  参考文献：
  名称：

  Efficient Zirconocene-Coupling of Silicon-Substituted Diynes to Polymers and Macrocycles

  摘要：

  The zirconocene-coupling of diynes with internal silicon substituents, MeC=CMe2SiArSiMe2C=CMe (1: Ar = 1,4-C6H4; 2: Ar = 1,3-C6H4; 3: Ar = 4,4'-C6H4C6H4), generates regiospecific polymers containing zirconacyclopentadiene in the main chain (5-7). These organometallic polymers hydrolyze cleanly to butadienediyl polymers of the type [Me2SiArSiMe2CH=CMeCMe=CH](n) (11-13), and polymer 5 reacts with iodine to give the iodine-containing polymer [1,4-Me2SiC6H4SiMe2C(I)=CMeCMe=C(I)](n) (14). The organometallic polymers undergo facile and high-yield degradations to macrocycles under mild conditions (refluxing tetrahydrofuran solution). The size and shape of the resulting macrocycles depend upon the nature of the diyne spacer group. Thus, polymers 5 and 7 containing parallel diyne units convert to the trimeric macrocycles [Me2SiArSiMe2C4Me2ZrCp2](3) (15: Ar = 1,4-C6H4; 24: Ar = 4,4'-C6H4C6H4), while polymer 6 gives the dimeric macrocycle [1,3-Me2SiC6H4SiMe2C4Me2ZrCp2](2) (18). The dimeric macrocycle [Me2SiC6H4-SiMe2C6H4SiMe2C4Me2ZrCp2](2) (20) was obtained directly from the zirconocene coupling of Me2Si[(1,4-C6H4)SiMe2(C=CMe)](2) (4) by heating the reaction mixture to reflux. In. similar manner, the diyne Me2Si(C=CMe)(2) was converted in high yield to the hexameric macrocycle [Me2SiC4Me2ZrCp2](6) (22). The macrocycles 15, [1,4-Me2SiC6H4SiMe2C4Me2H2](3) (16), and 18 were characterized by single-crystal X-ray crystallography. Molecules of 15 adopt a nearly planar Cg macrocyclic structure with a cavity described by an average transannular Si ... Si distance of 13.2 Angstrom, while the hydrolyzed macrocycle 16 has a chair conformation. This conformation change results from conversion of cis diene groups in the zirconacyclopendiene fragments to trans diene groups in 16. The high-yield formation of macrocycles apparently results from the reversible nature of the alkyne-coupling reaction, which allows for a low-energy pathway to the smallest macrocycle possessing minimal ring strain.

  DOI：

  10.1021/ja973180u
• 作为产物：
  描述：

  二乙氧基二甲基硅烷 、 4,4'-二溴联苯 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 以27%的产率得到4,4'-bis(ethoxy dimethyl silyl)biphenyl
  参考文献：
  名称：

  Synthesis of new microporous layered organic–inorganic hybrid nanocomposites by alkoxysilylation of a crystalline layered silicate, ilerite

  摘要：

  我们通过对4,4'-联苯桥接的烷氧基硅烷化合物进行烷氧基硅烷化，开发了微孔有机-无机混合纳米复合材料，这些化合物在每个4,4'-联苯单元的末端含有三乙氧基硅基、甲基二乙氧基硅基和二甲基乙氧基硅基团（(CH3)n(C2H5O)3-n-Si-C12H8-Si-(OC2H5)3-n(CH3)n，n = 0、1或2，分别简称为BESB(0)、BESB(2)和BESB(4)，其中括号中的数字表示这些分子中的甲基数量），并且它们嵌入在结晶层状硅酸盐（搭石）之间。XRD、29Si固态NMR和荧光光谱揭示，BESB分子通过缩合固定化并形成桥接，既与H-搭石，也与BESB分子之间形成相互作用。层间结构表现出不同的分子排列。BESB(0)和BESB(4)分子以单层排列的形式存在，其中BESB(0)分子由于紧密堆积形成与二聚体相似的低聚物种。BESB(2)分子主要在层间形成双层状聚集体。这些结构差异是由于BESB分子的反应性不同，从而控制它们在层间的聚合。最终得到的BESB(0)-和BESB(2)-搭石具有高微孔性，BET比表面积分别为508和578 m²/g。由于成功的表面改性，微孔的甲苯吸附性优于其他几种多孔硅材料。因此，这种方法提供了一种构建新型微孔纳米复合材料的新途径，是提高分离和催化应用中选择性和活性的关键。

  DOI：

  10.1039/b610088k

文献信息

• Two-component dental material crosslinking by addition, by way of a hydrosilylation reaction, having rigid and/or voluminous groups as well as great flexural strength
  申请人：Bublewitz Alexander

  公开号：US20050171233A1

  公开（公告）日：2005-08-04

  A two-component dental material addition-crosslinking by way of hydrosilylation contains (a) one or more compounds having vinyl groups in the molecule, (b) at least one organohydrogen silicone compound, and (c) at least one catalyst. The at least one compound (a) and/or the at least one compound (b) includes as the first structural unit, at least one voluminous and/or rigid group, and as the second structural unit, at least two alkenyl-functional or at least two hydrogen-functional silyl units. The second structural unit is bound to the first structural unit (i) directly, (ii) by way of an oxygen atom, (iii) by way of a spacer group, or (iv) by way of a spacer group according to (iii), which is bound to the first structural unit by way of an oxygen atom.

  一种通过氢硅烷化进行加成交联的两组分牙科材料包含（a）分子中含有乙烯基团的一个或多个化合物，（b）至少一种有机氢硅烷化合物，以及（c）至少一种催化剂。至少一种化合物（a）和/或至少一种化合物（b）包括作为第一结构单元的至少一个体积庞大和/或刚性基团，以及作为第二结构单元的至少两个烯基功能或至少两个氢功能硅基团。第二结构单元通过以下方式与第一结构单元结合：（i）直接，（ii）通过氧原子，（iii）通过间隔基团，或（iv）根据（iii）通过间隔基团，该间隔基团通过氧原子与第一结构单元结合。
• Efficient Zirconocene-Coupling of Silicon-Substituted Diynes to Polymers and Macrocycles
  作者：Shane S. H. Mao、Feng-Quan Liu、T. Don Tilley

  DOI：10.1021/ja973180u

  日期：1998.2.1

  The zirconocene-coupling of diynes with internal silicon substituents, MeC=CMe2SiArSiMe2C=CMe (1: Ar = 1,4-C6H4; 2: Ar = 1,3-C6H4; 3: Ar = 4,4'-C6H4C6H4), generates regiospecific polymers containing zirconacyclopentadiene in the main chain (5-7). These organometallic polymers hydrolyze cleanly to butadienediyl polymers of the type [Me2SiArSiMe2CH=CMeCMe=CH](n) (11-13), and polymer 5 reacts with iodine to give the iodine-containing polymer [1,4-Me2SiC6H4SiMe2C(I)=CMeCMe=C(I)](n) (14). The organometallic polymers undergo facile and high-yield degradations to macrocycles under mild conditions (refluxing tetrahydrofuran solution). The size and shape of the resulting macrocycles depend upon the nature of the diyne spacer group. Thus, polymers 5 and 7 containing parallel diyne units convert to the trimeric macrocycles [Me2SiArSiMe2C4Me2ZrCp2](3) (15: Ar = 1,4-C6H4; 24: Ar = 4,4'-C6H4C6H4), while polymer 6 gives the dimeric macrocycle [1,3-Me2SiC6H4SiMe2C4Me2ZrCp2](2) (18). The dimeric macrocycle [Me2SiC6H4-SiMe2C6H4SiMe2C4Me2ZrCp2](2) (20) was obtained directly from the zirconocene coupling of Me2Si[(1,4-C6H4)SiMe2(C=CMe)](2) (4) by heating the reaction mixture to reflux. In. similar manner, the diyne Me2Si(C=CMe)(2) was converted in high yield to the hexameric macrocycle [Me2SiC4Me2ZrCp2](6) (22). The macrocycles 15, [1,4-Me2SiC6H4SiMe2C4Me2H2](3) (16), and 18 were characterized by single-crystal X-ray crystallography. Molecules of 15 adopt a nearly planar Cg macrocyclic structure with a cavity described by an average transannular Si ... Si distance of 13.2 Angstrom, while the hydrolyzed macrocycle 16 has a chair conformation. This conformation change results from conversion of cis diene groups in the zirconacyclopendiene fragments to trans diene groups in 16. The high-yield formation of macrocycles apparently results from the reversible nature of the alkyne-coupling reaction, which allows for a low-energy pathway to the smallest macrocycle possessing minimal ring strain.
• Synthesis of new microporous layered organic–inorganic hybrid nanocomposites by alkoxysilylation of a crystalline layered silicate, ilerite
  作者：Ryo Ishii、Takuji Ikeda、Tetsuji Itoh、Takeo Ebina、Toshirou Yokoyama、Takaaki Hanaoka、Fujio Mizukami

  DOI：10.1039/b610088k

  日期：——

  We have developed microporous organic–inorganic hybrid nanocomposites by alkoxysilylation of 4,4′-biphenyl-bridged alkoxysilane compounds, which contain triethoxysilyl, methyldiethoxysilyl, and dimethylethoxysilyl groups at each end of the 4,4′-biphenylene unit ((CH3)n(C2H5O)3−n-Si-C12H8-Si-(OC2H5)3−n(CH3)n, n = 0, 1, or 2, abbreviated as BESB(0), BESB(2), or BESB(4), respectively, where the number in parentheses indicates the number of methyl groups in these molecules), in the interlayer of a crystalline layered silicate, ilerite. XRD, 29Si solid-state NMR and fluorescence spectroscopy revealed the immobilization and bridging formation of the BESB molecules between the silicate layers by condensation, not only with H-ilerite, but also with the BESB molecules. The interlayer structures exhibited different molecular arrangements. BESB(0) and BESB(4) molecules are present as a monolayer arrangement in which BESB(0) molecules form the oligomeric species caused by close stacking like a dimer. BESB(2) molecules form mainly bilayer-like aggregates in the interlayer. The structural differences are caused by the different reactivities of the BESB molecules, which control their polymerization in the interlayer. The resultant BESB(0)- and BESB(2)-ilerite had high microporosity with BET surface areas (508 and 578 m2 g−1 for BESB(0)- and BESB(2)-ilerite, respectively). The micropores showed higher toluene adsorptivity than several other porous silica materials due to the successful surface modification. Consequently, this approach provides a new method for constructing novel microporous nanocomposites, the key to improved selectivity and activity in separation and catalytic applications.

  我们通过对4,4'-联苯桥接的烷氧基硅烷化合物进行烷氧基硅烷化，开发了微孔有机-无机混合纳米复合材料，这些化合物在每个4,4'-联苯单元的末端含有三乙氧基硅基、甲基二乙氧基硅基和二甲基乙氧基硅基团（(CH3)n(C2H5O)3-n-Si-C12H8-Si-(OC2H5)3-n(CH3)n，n = 0、1或2，分别简称为BESB(0)、BESB(2)和BESB(4)，其中括号中的数字表示这些分子中的甲基数量），并且它们嵌入在结晶层状硅酸盐（搭石）之间。XRD、29Si固态NMR和荧光光谱揭示，BESB分子通过缩合固定化并形成桥接，既与H-搭石，也与BESB分子之间形成相互作用。层间结构表现出不同的分子排列。BESB(0)和BESB(4)分子以单层排列的形式存在，其中BESB(0)分子由于紧密堆积形成与二聚体相似的低聚物种。BESB(2)分子主要在层间形成双层状聚集体。这些结构差异是由于BESB分子的反应性不同，从而控制它们在层间的聚合。最终得到的BESB(0)-和BESB(2)-搭石具有高微孔性，BET比表面积分别为508和578 m²/g。由于成功的表面改性，微孔的甲苯吸附性优于其他几种多孔硅材料。因此，这种方法提供了一种构建新型微孔纳米复合材料的新途径，是提高分离和催化应用中选择性和活性的关键。