1,3-bis(chlorodimethylsilyl)benzene | 74606-84-1

• 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(chlorodimethylsilyl)benzene
• 英文别名: Chloro-[3-[chloro(dimethyl)silyl]phenyl]-dimethylsilane
• CAS: 74606-84-1
• 化学式: C₁₀H₁₆Cl₂Si₂
• 分子量: 263.314
• InChiKey: VOBYVDQTCYHZPW-UHFFFAOYSA-N

物化性质

• 沸点：
  293.4±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-bis(chlorodimethylsilyl)benzene 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以65%的产率得到octamethylcyclo-di(m-silylphenylenedisiloxane)
  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
• 作为产物：
  描述：

  1,3,5-三溴苯 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 1,3-bis(chlorodimethylsilyl)benzene
  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

• An ESR study on structures of a series of silylnitrenes
  作者：Yoshiteru Itagaki、Takashi Iseoka、Toshiyuki Iida、Joji Ohshita、Masaru Shiotani、Atsutaka Kunai

  DOI：10.1016/s0009-2614(01)01112-5

  日期：2001.11

  silyl azides resulted in the formation of triplet states even for those having two or three Si–N3 groups in a molecule. ESR spectra of the silylnitrenes exhibited a part of the fine structure at around 820 mT. All the silyl azides studied gave nearly identical D-values (ca. ) and much larger than those in phenylnitrenes. The results suggested that electron spins are localized in the nitrogen p-orbitals

  通过ESR研究了由叠氮化硅形成的一系列甲硅烷基氮烯的结构。甚至对于分子中具有两个或三个Si–N 3基团的那些，所有甲硅烷基叠氮化物的γ辐照和光照射也会导致形成三重态。甲硅烷基氮烯的ESR光谱在820 mT附近显示出部分精细结构。所有研究过的甲硅烷基叠氮化物都给出了几乎相同的D值（ca. ），并且比苯硝烯中的D值大得多。结果表明，电子自旋在很大程度上位于氮p轨道上，并根据腈–Si–N的单硅烷键来解释，即中断自旋离域。
• Silylative decarbonylation: a new route to arylsilanes
  作者：Jonathan D. Rich

  DOI：10.1021/ja00197a058

  日期：1989.7

  procedure is tolerant of a variety of aromatic substituents, for example, alkyl, halo, nitro, cyano, imide, acid anhydride, etc., and the synthesis of several new substituted aromatic chlorosilanes containing benzoyl chloride and phthalic anhydride moieties is described. Chloromethyldisilane starting reagents are available from the direct reaction of methyl chloride and silicon, making this methodology

  描述了一种通过钯催化的甲基氯乙硅烷和芳族酰氯反应制备芳族氯硅烷的新合成方法。甲硅烷基化脱羰过程是无溶剂的，可以利用低金属催化剂负载量（500-1,000 ppm Pd），在温和条件（145°C）下进行，并且选择性地以良好的产率（通常为 60-85%）得到芳族氯硅烷。该程序可以容忍多种芳族取代基，例如烷基、卤素、硝基、氰基、酰亚胺、酸酐等，并且描述了几种新的含有苯甲酰氯和邻苯二甲酸酐部分的取代芳族氯硅烷的合成。氯甲基乙硅烷起始试剂可得自氯甲烷与硅的直接反应，
• Synthesis and Structural Aspects of Silicon-bridged [2.2]Metacyclophanes
  作者：Kozaburo Nishiyama、Tsunetoshi Sugawara

  DOI：10.1246/cl.1992.1409

  日期：1992.8

  The title compounds were synthesized and the structural aspects were examined by NMR spectroscopy.

  合成标题化合物并通过NMR光谱检查结构方面。
• Phenylenbis(silandiyl-triflate) als neuartige Synthesebausteine für vielfältig strukturierte Organosilizium-Polymere
  作者：Wolfram Uhlig

  DOI：10.1002/hlca.19940770409

  日期：1994.6.29

  Phenylenebis(silandiyl triflates) – New Synthetic Building Blocks for Variously Structured Organosilicon Polymers

  苯二双（硅烷基三氟甲磺酸酯）–各种结构的有机硅聚合物的新型合成构件
• 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.