1,4-bis(propyloxy)-2-iodo-5-trimethylsilylacetylenebenzene | 221292-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-bis(propyloxy)-2-iodo-5-trimethylsilylacetylenebenzene
• 英文别名: 1-iodo-4-(trimethylsilyl)ethynyl-2,5-dipropoxybenzene；2-iodo-5-(trimethylsilyl)ethynyl-1,4-dipropoxybenzene；2-(4-Iodo-2,5-dipropoxyphenyl)ethynyl-trimethylsilane
• CAS: 221292-49-5
• 化学式: C₁₇H₂₅IO₂Si
• 分子量: 416.374
• InChiKey: USMSDLVNYMBGDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis(propyloxy)-2-iodo-5-trimethylsilylacetylenebenzene 在 copper(l) iodide 、 potassium carbonate 、 二异丙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 1,4-dipropyloxy-2-ethynyl-5-(2-triisopropylsilylethinyl)benzene
  参考文献：
  名称：

  Soluble Ferrocene Conjugates for Incorporation into Self-Assembled Monolayers

  摘要：

  A series of phenylethynyl oligomers (I-V) possessing a ferrocene and thiol at each termini have been synthesized. These oligomers have been designed to overcome the inherent insolubility of this class of complexes by substitution at the phenyl groups with methyl and propoxy substituents. Several new reactions for preparing arenethiol-protected compounds are described. Interestingly, the generation of an arenethiol anion during base- or fluoride-catalyzed deprotection has been characterized.

  DOI：

  10.1021/jo982392m
• 作为产物：
  描述：

  1,4-bis(propyloxy)-2,5-diiodobenzene 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以56%的产率得到1,4-bis(propyloxy)-2-iodo-5-trimethylsilylacetylenebenzene
  参考文献：
  名称：

  Synthetic Routes toward Carborane-Wheeled Nanocars

  摘要：

  [GRAPHICS]A new set of aryleneethynylene derivatives bearing three, four, and six p-carboranes as potential wheels attached to a semirigid chassis have been designed and synthesized. These molecules are expected to move in predetermined patterns on atomically smooth surfaces, depending on their specific configuration.

  DOI：

  10.1021/jo701400t

文献信息

• Fullerene/Thiol-Terminated Molecules
  作者：Yasuhiro Shirai、Jason M. Guerrero、Takashi Sasaki、Tao He、Huanjun Ding、Guillaume Vives、Byung-Chan Yu、Long Cheng、Austen K. Flatt、Priscilla G. Taylor、Yongli Gao、James M. Tour

  DOI：10.1021/jo901701j

  日期：2009.10.16

  A series of fullerene-terminated oligo(phenylene ethynylene) (OPEs) have been synthesized for potential use in electronic or optoelectronic device monolayers. Electronic properties such as the energy levels and the distribution of HOMOs and LUMOs of fullerene-terminated OPEs have been calculated using the ab initio method at the B3LYP/6-31G(d) level. The calculations have revealed the concentration of frontier orbitals on the fullerene cage and a narrow distribution of HOMO-LUMO energy gaps. Ultraviolet photoelectron spectroscopy and inverse photoemission spectroscopy studies have been performed to further examine the electronic properties of the fullerene-terminated OPEs on gold surfaces. The obtained broad photoelectron spectra Suggest that there are strong intermolecular interactions in the fullerene self-assembled monolayers, and the small bandgap (similar to 1.5 eV), determined by the photoelectron spectroscopy, indicates the unique nature of the fullerene-terminated OPEs in which the C-60 moiety can be connected to the Au surface through the conjugated OPE backbone.
• Synthesis of a nanocar with organometallic wheels
  作者：Guillaume Vives、James M. Tour

  DOI：10.1016/j.tetlet.2009.01.042

  日期：2009.4

  A new class of nanovehicles incorporating trans-alkynyl(dppe)(2)ruthenium-based wheels is reported. A four-wheeled nanocar and a three-wheeled trimer were synthesized for future studies at the single molecule level. (C) 2009 Elsevier Ltd. All rights reserved.