2-[3-乙炔基-5-(2-三甲基硅乙炔基)苯基]乙炔基三甲基硅烷 | 599187-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[3-乙炔基-5-(2-三甲基硅乙炔基)苯基]乙炔基三甲基硅烷
• 英文名称: 3,5-bis(trimethylsilylethynyl)-1-ethynylbenzene
• 英文别名: Silane, [(5-ethynyl-1,3-phenylene)di-2,1-ethynediyl]bis[trimethyl-；2-[3-ethynyl-5-(2-trimethylsilylethynyl)phenyl]ethynyl-trimethylsilane
• CAS: 599187-53-8
• 化学式: C₁₈H₂₂Si₂
• 分子量: 294.544
• InChiKey: AUMHGDJKNVTQIX-UHFFFAOYSA-N

物化性质

• 沸点：
  349.5±42.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-[3-乙炔基-5-(2-三甲基硅乙炔基)苯基]乙炔基三甲基硅烷 在 吡啶 、 氧气 、 copper(l) chloride 作用下， 反应 0.67h， 以98%的产率得到1,4-di(3,5-bis-trimethylsilylethynylphenyl)butadiyne
  参考文献：
  名称：

  基于1,4-和1,3,5-乙炔基苯基亚基的pi扩展共轭合成纳米结构。碳树突单元。

  摘要：

  从3,5-二（三甲基甲硅烷基乙炔基）苯基乙炔和对-[3,5-二（三甲基甲硅烷基乙炔基）-1-乙炔基苯基]苯基乙炔开始，合成了纳米级共轭的1,4-和1,3,5-乙炔基苯基低聚物。钯（II）/铜（I）催化的方便卤代芳基衍生物交叉偶联反应，收率很高。通过特定的保护-脱保护方法有效地制备了末端乙炔。所获得的所有乙炔基苯基同系物均显示出荧光发射，每个乙炔基苯基单元的红移大约为20 nm，从而增加了共轭链。通过插入1，5-萘亚单元制备平行的共轭乙炔基苯基链，并且该化合物表现出荧光辐射发射。

  DOI：

  10.1021/jo034972b
• 作为产物：
  描述：

  1,3,5-三溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 34.0h， 生成 2-[3-乙炔基-5-(2-三甲基硅乙炔基)苯基]乙炔基三甲基硅烷
  参考文献：
  名称：

  基于1,4-和1,3,5-乙炔基苯基亚基的pi扩展共轭合成纳米结构。碳树突单元。

  摘要：

  从3,5-二（三甲基甲硅烷基乙炔基）苯基乙炔和对-[3,5-二（三甲基甲硅烷基乙炔基）-1-乙炔基苯基]苯基乙炔开始，合成了纳米级共轭的1,4-和1,3,5-乙炔基苯基低聚物。钯（II）/铜（I）催化的方便卤代芳基衍生物交叉偶联反应，收率很高。通过特定的保护-脱保护方法有效地制备了末端乙炔。所获得的所有乙炔基苯基同系物均显示出荧光发射，每个乙炔基苯基单元的红移大约为20 nm，从而增加了共轭链。通过插入1，5-萘亚单元制备平行的共轭乙炔基苯基链，并且该化合物表现出荧光辐射发射。

  DOI：

  10.1021/jo034972b

文献信息

• Synthesis and optical properties of conjugated N,N-dimethyl and thienyl end-capped 2,5-(arylethynyl)thiophene oligomer structures
  作者：J. Gonzalo Rodrı́guez、Antonio Lafuente、Laura Rubio、Jorge Esquivias

  DOI：10.1016/j.tetlet.2004.07.123

  日期：2004.9

  by the Cl2Pd(PPh3)2/CuI system, in good to excellent yields. The 2,5-di[(3′,5′-di(trimethylsilylethynyl)phenyl]x-1-ethynyl]thiophene oligomers were prepared by heterocoupling between 3′,5′-di[(trimethylsilylethynyl)phenyl]x-1-ethyne (n = 0–2) terminal acetylenes and 2,5-diiodothiophene, in excellent yields. The terminal acetylenes were efficiently prepared by a specific protection-deprotection methodology

  通过在末端乙炔之间进行杂偶合，合成对位封端的（N，N-二甲基氨基苯基）和2'-噻吩基乙炔基2,5-噻吩低聚物结构：p-（N，N-二甲基氨基苯基）乙炔（3）[或1- （p-（N，N-二甲基氨基苯基）-2- p-（乙炔基苯基）乙炔，4]；p-（β-乙烯基-2'-噻吩基）苯基乙炔（E -9）[或p-（β-乙炔基- Cl 2 Pd（PPh 3）2催化的2'-噻吩基）苯基乙炔11]和2,5-二碘噻吩/ CuI系统，良率至良率。通过3，，5'-二[（三甲基甲硅烷基乙炔基）苯基] x -1-之间的杂合制备2,5-二[（3'，5'-二（三甲基甲硅烷基乙炔基）苯基] x -1-乙炔基]噻吩低聚物乙炔（n  = 0–2）末端乙炔和2,5-二碘噻吩，收率很好。通过特定的保护-脱保护方法有效地制备了末端乙炔。所有获得的乙炔基苯基化合物均显示出荧光辐射发射，红移为随着链共轭增加的波长。
• Synthesis of carbon dendron nano-chains with π-extended conjugation based on linear 1,4-phenylethynyl and 1,5-naphthylethynyl subunits
  作者：J.Gonzalo Rodrı́guez、J.Luis Tejedor、Jorge Esquivias、Cristina Dı́az

  DOI：10.1016/s0040-4039(03)01615-0

  日期：2003.8

  A convenient and efficient synthesis of 3,5-di(trimethylsilylethynyl)phenylacetylene and p-[3,5-di(trimethylsilylethynyl)-1-phenylethynyl]phenylacetylene and the naphthylethynyl homologues terminal acetylenes of 5-(N,N-dimethylamino)naphthylethyne have been carried out. These terminal acetylene compounds serve to prepare nanometer-sized conjugated 1,3,5-tri(ethynylphenyl)benzene and 1,3,5-tri(ethynylnaphthyl)benzene

  3,5-二（三甲基甲硅烷基乙炔基）苯基乙炔和对-[3,5-二（三甲基甲硅烷基乙炔基）-1-苯基乙炔基]苯基乙炔和5-（N，N-二甲基氨基）萘乙炔的萘乙炔基同系物末端乙炔的简便有效合成已经进行了。这些末端乙炔化合物通过与1,3,5-三碘代苯催化杂化，用于制备纳米级的共轭1,3,5-三（乙炔基苯基）苯和1,3,5-三（乙炔基萘基）苯低聚物。由钯制成，收率极高。乙炔基苯基或乙炔基萘基同系物链均显示出荧光发射辐射，具有重要的量子产率。
• Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: fluorescence properties
  作者：J. Gonzalo Rodriguez、Jorge Esquivias、Antonio Lafuente、Laura Rubio

  DOI：10.1016/j.tet.2006.01.032

  日期：2006.3

  Nano conjugated thienylethenyl and thienylethynyl Compounds with controlled Structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynylphenyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(iodo)thiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of nanostructures based on 1,4- and 1,3,5-phenylethynyl units with π-extended conjugation. Carbon networks dendrimer base units
  作者：J.Gonzalo Rodrı́guez、J. Esquivias

  DOI：10.1016/s0040-4039(03)01137-7

  日期：2003.6

  A convenient and efficient synthesis of 3,5-di(silylethynyl)phenylacetylene and p-[3,5-di(silylethynyl)phenylethynyl]phenylacetylene has been carried out. These compounds serve to prepare nanometer-sized conjugated 1,4- and 1,3,5-phenylethynyl oligomers, by means of cross-coupling with a convenient haloaryl derivative, catalysed by palladium(H), in excellent yields. The phenylethynyl homologues show fluorescence emission, the wavelength of which is displaced by approximately 20 nm by each phenylethynyl unit increasing the conjugate chain. (C) 2003 Elsevier Science Ltd. All rights reserved.
• An effective, orthogonal deprotection strategy for differentially functionalized, linear and Y-shaped oligo phenylene ethynylenes
  作者：Kusum L. Chandra、Sheng Zhang、Christopher B. Gorman

  DOI：10.1016/j.tet.2007.05.006

  日期：2007.7

  Several methodologies for the selective deprotection acetylenes have been reported previously. However, as is shown here, they are often not reliable or convenient. Here, an approach is reported that is efficient and general. Use of this approach to synthesize several two- and three-armed oligo(phenylene ethynylene) molecules with differentiated end groups is reported. In addition, preliminary characterization of the fluorescent properties of some of these molecules and their ability to form self-assembled monolayers (SAMs) is reported. (C) 2007 Elsevier Ltd. All rights reserved.