bis(1-methyl-1-silafluorene) | 18758-43-5

• 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: bis(1-methyl-1-silafluorene)
• 英文别名: 5,5'-dimethyl-5H,5'H-[5,5']bidibenzosilolyl；5-Methyl-5-(5-methylbenzo[b][1]benzosilol-5-yl)benzo[b][1]benzosilole
• CAS: 18758-43-5
• 化学式: C₂₆H₂₂Si₂
• 分子量: 390.632
• InChiKey: VZAAIZODKRDSGC-UHFFFAOYSA-N

物化性质

• 熔点：
  185-186 °C
• 沸点：
  500.4±23.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  9-chloro-9-methyl-9-silafluorene 在 sodium 、 xylene 作用下， 生成 bis(1-methyl-1-silafluorene)
  参考文献：
  名称：

  Cyclic Organosilicon Compounds. II. Reactions Involving Certain Functional and Related Dibenzosilole Compounds

  摘要：

  DOI：

  10.1021/ja01546a017

文献信息

• Structure and Chemistry of 1-Silafluorenyl Dianion, Its Derivatives, and an Organosilicon Diradical Dianion
  作者：Yuxia Liu、Thomas C. Stringfellow、David Ballweg、Ilia A. Guzei、Robert West

  DOI：10.1021/ja011821m

  日期：2002.1.1

  also support electron delocalization in the silole ring of 3b. Dianion salt 3b underwent nucleophilic reactions with Me(3)SiCl and EtBr to form the corresponding disubstituted products. Benzaldehyde underwent reductive coupling in the presence of 3b. Slow oxidation of 3b yielded 1,1'-dipotassio-1,1'-bis(silafluorene) (16). The X-ray structure and (29)Si chemical shift (-38.0 ppm) of 16 indicate localized

  1-硅芴二价阴离子是通过1,1-二氯-1-硅芴在回流THF中钾还原合成的。1,1-dipotassio-1-silafluorene (3b) 的 X 射线结构显示五元硅酮环中的 CC 键长均衡和六元苯环中的 CC 键长交替，表明电子在芳香族离域西罗环。29.0 ppm 处的低场 (29) Si 化学位移和理论计算也支持 3b 的silole 环中的电子离域。Dianion 盐 3b 与 Me(3)SiCl 和 EtBr 发生亲核反应，形成相应的双取代产物。苯甲醛在 3b 存在下进行还原偶联。3b 的缓慢氧化产生 1,1'-dipotassio-1,1'-bis(silafluorene) (16)。X 射线结构和 (29)Si 化学位移 (-38. 0 ppm) of 16 表示在硅原子处有局部负电荷并且没有芳香特征。在 18-crown-6 存在的情况下加热 3b 的 DME/己烷溶液产生了一种新型的双自由基二价阴离子盐。
• Synthesis and characterization of dibenzannulated silole dianions. The 1,1-dilithiosilafluorene and 1,1′-dilithiobis(silafluorene) dianions
  作者：Seok-Bong Choi、Philip Boudjouk

  DOI：10.1016/s0040-4039(00)00920-5

  日期：2000.8

  Stirring of 1,1-dichloro-SiFl (1), (SiFl, silafluorene) in THF with excess lithium for 1 h gave a dark green solution of 1,1-dilithio-SiFl (2) in high yield. The dark red solution of the intermediate 1,1'-dilithio-(SiFl)(2) (3) was also observed from this reaction within 10 min. Treatment of 2 with excess trimethylchlorosilane gave the 1,1-bis(trimethylsilyl)-SiFl derivative (4) in 95% yield. Treatment of the dark red solution of 3 and 2 with excess methyliodide gave the 1,1'-dimethyl-bis(SiFl) (5) and 1,1-dimethyl-SiFl (6) derivatives in a 4.1 ratio. The upheld locations of the Si-29 resonances of dianions 2 and 3 (-1.09 ppm and -39.25 ppm, respectively) are consistent with pi-electron localization on the silicon atoms. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Cyclic Organosilicon Compounds. II. Reactions Involving Certain Functional and Related Dibenzosilole Compounds
  作者：Henry Gilman、Richard D. Gorsich

  DOI：10.1021/ja01546a017

  日期：1958.7