乙氧基-[4-[乙氧基(二甲基)甲硅烷基]苯基]-二甲基硅烷 | 2615-23-8

• 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
• 中文名称: 乙氧基-[4-[乙氧基(二甲基)甲硅烷基]苯基]-二甲基硅烷
• 英文名称: 1,4-bis(ethoxydimethylsilyl)benzene
• 英文别名: Si,Si'-diethoxy-Si,Si,Si',Si'-tetramethyl-Si,Si'-p-phenylene-bis-silane；Si,Si'-Diaethoxy-Si,Si,Si',Si'-tetramethyl-Si,Si'-p-phenylen-bis-silan；1,4-Bis-(aethoxy-dimethyl-silyl)-benzol；Silane, 1,4-phenylenebis[ethoxydimethyl-；ethoxy-[4-[ethoxy(dimethyl)silyl]phenyl]-dimethylsilane
• CAS: 2615-23-8
• 化学式: C₁₄H₂₆O₂Si₂
• 分子量: 282.53
• InChiKey: UHJWZLRWUMOYIJ-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：

  乙氧基-[4-[乙氧基(二甲基)甲硅烷基]苯基]-二甲基硅烷 在 正丁基锂 、 乙酰氯 作用下， 反应 6.5h， 生成 [4-[Dimethyl(prop-1-ynyl)silyl]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 、 1,4-二溴苯 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成 乙氧基-[4-[乙氧基(二甲基)甲硅烷基]苯基]-二甲基硅烷
  参考文献：
  名称：

  Siloxa-bridged-cyclophanes featuring benzene, thiophene and pyridine units

  摘要：

  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。

  DOI：

  10.1039/b211045h

文献信息

• Interaction of Alkoxysilanes and Acetoxysilanes¹
  作者：W. J. HAGGERTY、L. W. BREED

  DOI：10.1021/jo01351a076

  日期：1961.7
• Arylenedisilanols
  作者：L.W. Breed、R.L. Elliott

  DOI：10.1016/s0022-328x(00)92425-2

  日期：1967.7
• Epoxy-substituted organosilicon compounds and method for preparing the same
  申请人：WESTINGHOUSE ELECTRIC CORP

  公开号：US02883395A1

  公开（公告）日：1959-04-21
• p-Phenylenedisilanes¹
  作者：L. W. BREED、WILLIAM J. HAGGERTY、FRED BAIOCCHI

  DOI：10.1021/jo01079a037

  日期：1960.9
• 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.