3,7-di-tert-butyl-5,5-diphenyl-5H-dibenzo[b,d]silole | 1190956-31-0

• 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: 3,7-di-tert-butyl-5,5-diphenyl-5H-dibenzo[b,d]silole
• 英文别名: 3,7-Ditert-butyl-5,5-diphenylbenzo[b][1]benzosilole
• CAS: 1190956-31-0
• 化学式: C₃₂H₃₄Si
• 分子量: 446.707
• InChiKey: RNZJAFSNZUVAJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-溴-4,4-二-叔丁基-1,1-联苯 在 吡啶 、 正丁基锂 、 N-羟基邻苯二甲酰亚胺 、 tert-butylammonium hexafluorophosphate(V) 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 7.59h， 生成 3,7-di-tert-butyl-5,5-diphenyl-5H-dibenzo[b,d]silole
  参考文献：
  名称：

  电催化 Sila-Friedel-Crafts 反应合成二苯甲硅烷

  摘要：

  通过从联芳基氢硅烷开始的分子内 C-H/Si-H 脱氢偶联策略，开发了一种用于制备二苯甲硅烷的新型电催化方法。供电和吸电取代基团都可以用于这种转化，并且可以以中等至极好的收率获得所需的二苯并噻咯产物。在以前的文献和我们的对照实验的基础上提出了一种 sila-Friedel-Crafts 反应机理。

  DOI：

  10.1002/adsc.202100262

文献信息

• Visible-Light Induced Radical Silylation for the Synthesis of Dibenzosiloles via Dehydrogenative Cyclization
  作者：Chao Yang、Jing Wang、Jianhua Li、Wenchao Ma、Kun An、Wei He、Chao Jiang

  DOI：10.1002/adsc.201800417

  日期：2018.8.17

  A visible‐light induced radical silylation to dibenzosiloles from biarylhydrosilanes is described. The products were obtained in satisfactory yields under mild and water/air compatible conditions, providing an efficient and practical method for the synthesis of difunctionalized siloles by using a cheap organic dye photocatalyst. The method is tolerated by a wide range of functional groups and has a

  描述了由可见光诱导的从联芳基氢硅烷到二苯并甲硅烷基的自由基甲硅烷基化。该产物在温和的和水/空气相容的条件下以令人满意的产率获得，提供了通过使用便宜的有机染料光催化剂来合成双官能化的硅烷的有效和实用的方法。该方法可被多种官能团所耐受，并且具有广泛的底物范围。光/暗实验和量子产率测量为光催化途径而不是链过程提供了支持。
• B(C₆F₅)₃-Catalyzed Synthesis of Benzofused-Siloles
  作者：Liam D. Curless、Michael J. Ingleson

  DOI：10.1021/om501033p

  日期：2014.12.22

  a weak base forms silafluorenes with H2 as the only byproduct. Attempts to extend this approach to synthesize siloles derived from 2,2′-bithiophenes and N-Me-2-Ph-indole resulted in competing reactivity, including protodesilylation. B(C6F5)3 also catalyzed the one-pot, two-step formation of silaindenes from aryl-alkynes by alkyne trans-hydrosilylation, followed by an intramolecular Sila-Friedel–Crafts

  由B（C 6 F 5）3和弱碱催化的2-（SiR 2 H）-联苯的脱氢硅烷化反应形成了以H 2为唯一副产物的硅芴。尝试将该方法扩展为合成由2,2'-联噻吩和N -Me-2-Ph-吲哚衍生的甲硅烷导致竞争的反应性，包括原去甲硅烷基化。B（C 6 F 5）3还催化了炔烃的反式氢化硅烷化作用，由芳基炔烃一锅，两步形成硅氢化茚，然后通过弱碱促进了分子内Sila-Friedel-Crafts反应。
• Application of the sila-Friedel–Crafts reaction to the synthesis of π-extended silole derivatives and their properties
  作者：Shunsuke Furukawa、Junji Kobayashi、Takayuki Kawashima

  DOI：10.1039/c0dt00136h

  日期：——

  The intramolecular sila-Friedel–Crafts reaction was developed as a new method for the construction of a dibenzosilole skeleton. This reaction proceeds under mild conditions to afford the target in relatively good yield, indicating its availability as a versatile synthetic method. This reaction can be applied to the synthesis of π-extended silole derivatives such as ladder-type silafluorene 8 and spiro-type silabifluorene 9. Furthermore, the synthesis of two-dimensionally extended silole derivatives utilizing the sila-Friedel–Crafts reaction as the multiple intramolecular cyclization was achieved, including the first synthesis of trisilasumanene 18. The X-ray crystallographic analysis of trisilasumanene 18 demonstrated the planarity in the main π-framework, in contrast to sumanene and its sulfur analogue, trithiasumanene, bearing the bowl-shaped structures. In the UV-vis absorption spectra, the absorption bands of triphenylenosiloles 18 and 19 were slightly red-shifted compared to that of hexabutoxytriphenylene 22. The weak absorption bands were also observed in the longer-wavelength region in 18 and 19, which is derived from σ*–π* conjugation of the silole skeletons. In addition, 18 and 19 showed the blue fluorescence in dichloromethane and in the solid state.

  分子内 Sila-FriedelâCrafts 反应是一种构建二苯甲硅基骨架的新方法。该反应在温和的条件下进行，目标物的产率相对较高，表明它是一种多功能合成方法。该反应可用于合成Ï-扩展硅烯衍生物，如梯形硅芴 8 和螺形硅杂芴 9。此外，利用硅拉-弗里德尔-卡夫斯反应作为分子内多次环化，合成了二维延伸的硅烯衍生物，包括首次合成了三硅芴18。三硅基马来烯 18 的 X 射线晶体学分析表明，其主 Ï 框架为平面结构，而苏木烯及其硫类似物三硫代马来烯则为碗状结构。在紫外-可见吸收光谱中，三苯基硅烷 18 和 19 的吸收带与六丁氧基三亚苯 22 的吸收带相比略有红移。在 18 和 19 的较长波长区域也观察到了微弱的吸收带，这是硅烯骨架的Ï*âÏ*共轭作用产生的。此外，18 和 19 在二氯甲烷中和固态下显示出蓝色荧光。
• Development of a Sila-Friedel−Crafts Reaction and Its Application to the Synthesis of Dibenzosilole Derivatives
  作者：Shunsuke Furukawa、Junji Kobayashi、Takayuki Kawashima

  DOI：10.1021/ja906566r

  日期：2009.10.14

  An intramolecular sila-Friedel-Crafts reaction was developed and applied to the synthesis of dibenzosilole derivatives. This reaction proceeds under mild conditions to afford the target in relatively high yield, indicating its availabilty as a versatile synthetic method. The synthesis of trisilasumanene, a silicon analogue of sumanene, was achieved using the present reaction.
• Synthesis of Dibenzosiloles through Electrocatalytic Sila‐Friedel‐Crafts Reaction
  作者：Pan Han、Mengyun Yin、Haiqiong Li、Jundan Yi、Linhai Jing、Bangguo Wei

  DOI：10.1002/adsc.202100262

  日期：2021.6.8

  for the preparation of dibenzosiloles was developed through intramolecular C−H/Si−H dehydrogenative coupling strategy starting from biarylhydrosilanes. Both electro-donating and electro-withdrawing substitution groups were tolerated for this transformation, and the desired dibenzosilole products could be obtained in moderate to excellent yields. A sila-Friedel-Crafts reaction mechanism was proposed

  通过从联芳基氢硅烷开始的分子内 C-H/Si-H 脱氢偶联策略，开发了一种用于制备二苯甲硅烷的新型电催化方法。供电和吸电取代基团都可以用于这种转化，并且可以以中等至极好的收率获得所需的二苯并噻咯产物。在以前的文献和我们的对照实验的基础上提出了一种 sila-Friedel-Crafts 反应机理。