3,5-bis(trimethylsilylethynyl)-1-(3-hydroxy-3-methyl-1-butynyl)benzene | 599187-51-6

• 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: 3,5-bis(trimethylsilylethynyl)-1-(3-hydroxy-3-methyl-1-butynyl)benzene
• 英文别名: 4-[3,5-bis(2-trimethylsilylethynyl)phenyl]-2-methylbut-3-yn-2-ol
• CAS: 599187-51-6
• 化学式: C₂₁H₂₈OSi₂
• 分子量: 352.624
• InChiKey: HAURTEXLDFHBGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,5-bis(trimethylsilylethynyl)-1-(3-hydroxy-3-methyl-1-butynyl)benzene 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 35.0h， 生成 2-[3-[2-[4-[2-[4-[2-[4-[2-[4-[2-[3,5-Bis(2-trimethylsilylethynyl)phenyl]ethynyl]phenyl]ethynyl]phenyl]ethynyl]phenyl]ethynyl]phenyl]ethynyl]-5-(2-trimethylsilylethynyl)phenyl]ethynyl-trimethylsilane
  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 、 copper(l) iodide 、 三乙胺 作用下， 反应 30.0h， 生成 3,5-bis(trimethylsilylethynyl)-1-(3-hydroxy-3-methyl-1-butynyl)benzene
  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 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.
• Construction of Snowflake-Shaped Dendritic Covalent Assemblies with Rigid Conjugated Networks
  作者：Masatoshi Kozaki、Shirou Morita、Shuichi Suzuki、Keiji Okada

  DOI：10.1021/jo3014512

  日期：2012.11.2

  A convergent method for the construction of shape-persistent nanoscale assemblies with conjugated backbones was developed. The copper-free Sonogashira coupling reaction was successfully applied to the formation of multiple covalent connections between conjugated terminals (iodide substituted aryl groups) of AB(2)-type outer components and four conjugated terminals (acetylenic bonds) of an inner A(4)-type core dendrimer. The conjugated networks in the starting components are expanded during the assembly process to afford nanoscale dendritic conjugated networks of the type A(4)(AB(2))(4), which have a porphyrin core, and longer (3.9 or 4.5 nm) and shorter (1.6 nm) conjugated chains. Fluorescence measurements revealed that singlet energy is effectively transferred in the assemblies from peripheral benzyl ether units and conjugated chains to the free base porphyrin core.