1,3-bis(ethoxydimethylsilyl)benzene | 16165-95-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,3-bis(ethoxydimethylsilyl)benzene
• 英文别名: Ethoxy-[3-[ethoxy(dimethyl)silyl]phenyl]-dimethylsilane
• CAS: 16165-95-0
• 化学式: C₁₄H₂₆O₂Si₂
• 分子量: 282.53
• InChiKey: IGYCKASZFZUQLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  1,3-bis(ethoxydimethylsilyl)benzene 在 乙酰氯 作用下， 反应 6.0h， 以97%的产率得到1,3-bis(chlorodimethylsilyl)benzene
  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：

  2-氯乙氧基(二甲基)硅烷 、 1,3-二溴苯 生成 1,3-bis(ethoxydimethylsilyl)benzene
  参考文献：
  名称：

  Arylenedisilanols

  摘要：

  DOI：

  10.1016/s0022-328x(00)92425-2

文献信息

• Siloxa-bridged-cyclophanes featuring benzene, thiophene and pyridine units
  作者：Audrey Moores、Christian Defieber、Nicolas Mézailles、Nicole Maigrot、Louis Ricard、Pascal Le Floch

  DOI：10.1039/b211045h

  日期：——

  Two octamethyldisiloxa-bridged [3.3]cyclophanes (1 and 2) and a dodecamethyltrissiloxa-bridged [3.3.3]-cage compound (3) were prepared by hydrolysis of the chlorosilyl monomers. This general route was also employed for the preparation of two octamethyldisiloxa-bridged [3.3]heterophanes featuring two thiophene (14) or pyridine (17) moities.

  通过水解氯硅烷单体，制备了两个八甲基二硅氧烷键合的[3.3]环烷（1 和 2）和一个十二甲基三硅氧烷键合的[3.3.3]笼状化合物（3）。此外，还采用这种一般方法制备了两种具有两个噻吩（14）或吡啶（17）分子的八甲基二硅氧烷键合[3.3]杂环化合物。
• Electron Transfer between Two Silyl-Substituted Phenylene Rings:  EPR/ENDOR Spectra, DFT Calculations, and Crystal Structure of the One-Electron Reduction Compound of a Di(<i>m</i>-silylphenylenedisiloxane)
  作者：Cosmina Dutan、Sylvie Choua、Théo Berclaz、Michel Geoffroy、Nicolas Mézailles、Audrey Moores、Louis Ricard、Pascal Le Floch

  DOI：10.1021/ja0209060

  日期：2003.4.1

  the delocalization of the unpaired electron on the two phenyl rings of 4. The measured hyperfine interactions agree with those calculated by DFT for the optimized structure of 4(.-). Direct information on the structure of this anion is obtained from the X-ray diffraction of crystals grown at -18 degrees C in reduced solutions containing 4, potassium, and crown ether in a THF/hexane mixture. Both DFT

  该阴离子结构的直接信息是通过在 -18 摄氏度下在 THF/己烷混合物中含有 4、钾和冠醚的​​还原溶液中生长的晶体的 X 射线衍射获得的。DFT 和晶体结构都清楚地表明了由向 4 添加一个电子引起的几何变化：苯基间距离急剧减小，导致两个环的部分重叠。4(.-) 的结构是两个芳环之间电子转移 (ET) 过渡态的模型。采用这种结构的主要原因在于这两个片段的 LUMO（pi 轨道）之间的键合相互作用；此外，宏观周期的约束可能有助于这种结构的稳定。