2,3,7,8,12,13-Hexabutoxy-5,5,10,10,21,21-hexakis-phenyl-5,10,21-trisilaheptacyclo[12.6.1.04,19.06,18.09,17.011,16.015,20]henicosa-1,3,6,8,11,13,15(20),16,18-nonaene | 1190956-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3,7,8,12,13-Hexabutoxy-5,5,10,10,21,21-hexakis-phenyl-5,10,21-trisilaheptacyclo[12.6.1.04,19.06,18.09,17.011,16.015,20]henicosa-1,3,6,8,11,13,15(20),16,18-nonaene
• CAS: 1190956-38-7
• 化学式: C₇₈H₈₄O₆Si₃
• 分子量: 1201.78
• InChiKey: FUALGGKPKZXCMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.29
• 重原子数：
  87
• 可旋转键数：
  30
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2,4,5,8,9-hexabutoxy-3,3,10,10-tetraphenyl-6-diphenylsilyltriphenyleno[1,12-bcd:4,5-b'c'd']disilole 在 2,6-二甲基吡啶 、 三苯碳四(五氟苯基)硼酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以18%的产率得到2,3,7,8,12,13-Hexabutoxy-5,5,10,10,21,21-hexakis-phenyl-5,10,21-trisilaheptacyclo[12.6.1.04,19.06,18.09,17.011,16.015,20]henicosa-1,3,6,8,11,13,15(20),16,18-nonaene
  参考文献：
  名称：

  Development of a Sila-Friedel−Crafts Reaction and Its Application to the Synthesis of Dibenzosilole Derivatives

  摘要：

  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.

  DOI：

  10.1021/ja906566r

文献信息

• 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。