1,1-dimethyl-3,4-diphenylsilole | 55227-55-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1-dimethyl-3,4-diphenylsilole
• 英文别名: 1,1-dimethyl-3,4-diphenyl-1H-silole；1,1-Dimethyl-3,4-diphenyl-1H-silole
• CAS: 55227-55-9
• 化学式: C₁₈H₁₈Si
• 分子量: 262.426
• InChiKey: MVNVMCKXRSSBIA-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  350.7±42.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1,1-dimethyl-3,4-diphenylsilole 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 N-氯代酞酰亚胺 、 碘 、 三乙胺 、 zinc(II) chloride 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 26.5h， 生成 2-[(4-iodophenyl)ethynyl]-1,1-dimethyl-3,4-diphenyl-5-(phenylethynyl)silole
  参考文献：
  名称：

  A Controlled, Iterative Synthesis and the Electronic Properties of Oligo[(p-phenyleneethynylene)-alt-(2,5-siloleneethynylene)]s

  摘要：

  An introductory series of conjugated siloleneethynylene co-oligomers has been prepared from a key 2-chloro-5-iodosilole intermediate via site-specific cross-coupling reactions. The tetramer (9) and pentamer (10) both exhibit absorption maxima matching those of the corresponding silole copolymers. Extinction coefficients for the oligomers in this series are large, and in the case of the pentamer (10) the value exceeds 180 000 M-1 cm(-1). The compounds all emit in the visible region with the greatest quantum efficiencies being 8.97 x 10(-2) (monomer) and 2.99 x 10(-2) (pentamer).

  DOI：

  10.1021/ja047983a
• 作为产物：
  描述：

  2,3-二苯基-1,3-丁二烯 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 氧气 、 亚甲兰 、 异氰酸苯酯 、 magnesium 作用下， 以 氯仿 为溶剂， 反应 28.0h， 生成 1,1-dimethyl-3,4-diphenylsilole
  参考文献：
  名称：

  1,1-二甲基-2,3,4,5-四苯基-1-硅环戊二烯，1,1-二甲基-2,5-二苯基-1-硅环戊二烯和1,1-二甲基-3,4的Diels-Alder反应-二苯基-1-硅环戊二烯与马来酸酐；动力学测量

  摘要：

  1,1-二甲基-2,3,4,5-四苯基-1-硅环戊二烯，1,1-二甲基-2,5-二苯基-1-硅环戊二烯和1,1-二甲基-3,4的Diels-Alder反应已经进行了带有马来酸酐的-二苯基-2-硅杂环戊二烯的制备。这些二级反应的速率已通过1 H FT NMR在一定温度范围内测量。这些数据的阿累尼乌斯图得出了这些反应的激活参数。据报道，合成了1，1-二甲基-3，4-二苯基-1-硅环戊二烯。

  DOI：

  10.1016/0022-328x(88)80355-3

文献信息

• Water-soluble AIE luminogens for monitoring and retardation of fibrillation of amyloid proteins
  申请人：THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US09279806B2

  公开（公告）日：2016-03-08

  Compounds that exhibit aggregation induced emission (AIE), and more particularly to water-soluble conjugated polyene compounds that exhibit aggregation induced emission. The conjugated polyene compounds can be used as bioprobes for DNA detection, G-quadruplex identification, and potassium-ion sensing. The polyenes also can be utilized as an external fluorescent marker to study conformational structures, to monitor folding processes of label-free oligonucleotides with G-rich strand sequences, and to visualize DNA bands in PAGE assay. The polyenes have applications in high-throughput anticancer drug screening and are useful for the development of efficient anti-cancer drugs. Furthermore, the present subject matter can also be used to monitor fibrillation of amyloid proteins and to facilitate the storage and delivery thereof.

  表现出聚集诱导发光（AIE）特性的化合物，更具体地说是表现出聚集诱导发光特性的水溶性共轭聚烯烃化合物。这些共轭聚烯烃化合物可用作DNA检测的生物探针、G-四链体识别和钾离子感知。这些聚烯烃还可用作外部荧光标记物，用于研究构象结构，监测不带标签的富含G链序列的寡核苷酸的折叠过程，并在PAGE分析中可视化DNA条带。这些聚烯烃在高通量抗癌药物筛选中具有应用，并有助于开发高效的抗癌药物。此外，目前的主题还可用于监测淀粉样蛋白的纤维化，并促进其存储和传递。
• Silole-core phenylacetylene dendrimers and their application in detecting picric acid
  作者：Shanshan Li、Taohua Leng、Hanbin Zhong、Chengyun Wang、Yongjia Shen

  DOI：10.1002/jhet.796

  日期：2012.1

  Silole‐core phenylacetylene dendrimers were designed and synthesized, among them, the model compound (n = 0) and the first generation of the dendrimer (n = 1) were obtained by the reaction of 2,5‐dibromosilole with corresponding terminal alkynes, the second generation of the dendrimers (n = 2) was synthesized from 2,5‐diiodosilole. These compounds indicated the absorptions of both phenylacetylene dendrons

  设计并合成了以硅为核心的苯基乙炔树状大分子，其中，模型化合物（n = 0）和第一代树状大分子（n = 1）是通过2,5-二溴甲硅烷基与相应的末端炔烃反应得到的。第二代树枝状聚合物的（ñ= 2）由2,5-二碘硅烷合成。这些化合物表明苯乙炔树枝状分子（250-350 nm）和硅谷核（400-500 nm）均被吸收。第一代显示出从苯乙炔树枝状分子到硅烷核的有效能量转移，后者的能量转移效率高达80％。这些化合物用作苦味酸（PA）炸药的化学传感器，模型化合物和第一代化合物的Stern-Volmer常数分别为7120和5490 M -1。J.杂环化​​学。（2012）。
• Silylboranes Bearing Dialkylamino Groups on Silicon as Silylene Equivalents:  Palladium-Catalyzed Regioselective Synthesis of 2,4-Disubstituted Siloles
  作者：Toshimichi Ohmura、Kohei Masuda、Michinori Suginome

  DOI：10.1021/ja073896h

  日期：2008.2.6

  Silylpinacolboranes bearing dialkylamino groups on the silicon atom several as synthetic equivalents of silylene in palladium-catalyzed reactions with terminal alkynes, leading to the formation of 2, 4-disubstituted siloles in high yield. It was found that the amino group on the silicon atom was critically important for the reaction; no silole products were found in reactions using silylpinacolboranes carrying aryl, chloro, or alkoxy groups on the silicon atoms. Site-selective bromination of 1,1-dimethyl-2,4-diphenylsilole followed by Migita-Kasugi-Stille coupling with (arylalkynyl)tributylstannanes gave novel Pi-conjugated siloles with good total yields.
• (Trialkylstannyl)dimethylsilane as a new precursor of dimethylsilylene: a novel synthesis of 3,4-disubstituted 1-silacyclopenta-2,4-dienes
  作者：Kazutoshi Ikenaga、Kouji Hiramatsu、Norimitsu Nasaka、Satoshi Matsumoto

  DOI：10.1021/jo00071a009

  日期：1993.9

  In the presence of triphenylphosphinepalladium complexes, (trialkylstannyl)dimethylsilane rapidly reacted at room temperature with terminal acetylenes to give 3,4-disubstituted 1-silacyclopenta-2,4-dienes in moderate yield. The formation of 1-silacyclopentadiene derivatives is evidence for the generation of dimethylsilylene species from (trialkylstannyl)dimethylsilane.
• Diels–Alder reactions of C-phenylated siloles with 1,4-epoxy-1,4-dihydronaphthalene
  作者：S.I Kirin、D Vikić-Topić、E Mestrović、B Kaitner、M Eckert-Maksić

  DOI：10.1016/s0022-328x(98)00581-6

  日期：1998.9

  Preparation of a novel type of cycloadducts composed of a 7-silanorbornene ring condensed to the 7-oxanorbornene moiety (5-7) is described and their spectroscopic features are discussed in detail. The X-ray data for 5 are also presented. Finally, formation of silanole 8 by nucleophilic cleavage of an endocyclic silicon-carbon bond in 7 is described. (C) 1998 Elsevier Science S.A. All rights reserved.