[2-iodo-4-((S)-2-methyl-butoxy)-phenylethynyl]-trimethylsilane | 604800-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-iodo-4-((S)-2-methyl-butoxy)-phenylethynyl]-trimethylsilane
• 英文别名: [2-iodo-4-((S)-2-methylbutoxy)phenylethynyl]trimethylsilane；2-[2-iodo-4-[(2S)-2-methylbutoxy]phenyl]ethynyl-trimethylsilane
• CAS: 604800-40-0
• 化学式: C₁₆H₂₃IOSi
• 分子量: 386.348
• InChiKey: VEQSRZFUEODUEM-ZDUSSCGKSA-N

物化性质

• 沸点：
  374.6±42.0 °C(Predicted)
• 密度：
  1.29±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：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [2-iodo-4-((S)-2-methyl-butoxy)-phenylethynyl]-trimethylsilane 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis of Alkoxy-Substituted ortho-Phenylene Ethynylene Oligomers

  摘要：

  [GRAPHICS]This Letter describes the first published synthesis and characterization of alkoxy-substituted ortho-phenylene ethynylene (o-PE) oligomers. Sonogashira coupling was used to assemble discrete chain lengths, using a key monomer with orthogonal groups. Deprotection or activation allowed stepwise coupling to produce the dimer, trimer, and tetramer, while convergent coupling of appropriately substituted trimers produced the hexamer. The placement of alkoxy side chains renders these oligomers soluble in common organic solvents permitting solution characterization. Absorption and emission spectra of the trimer, tetramer, and hexamer are provided.

  DOI：

  10.1021/ol0352254
• 作为产物：
  描述：

  4-碘-3-硝基苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 甲烷 盐酸 、 copper(l) iodide 、 偶氮二甲酸二异丙酯 、 三氯化铁 、 一水合肼 、 三乙胺 、 三苯基膦 、 sodium nitrite 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 34.75h， 生成 [2-iodo-4-((S)-2-methyl-butoxy)-phenylethynyl]-trimethylsilane
  参考文献：
  名称：

  Synthesis of Alkoxy-Substituted ortho-Phenylene Ethynylene Oligomers

  摘要：

  [GRAPHICS]This Letter describes the first published synthesis and characterization of alkoxy-substituted ortho-phenylene ethynylene (o-PE) oligomers. Sonogashira coupling was used to assemble discrete chain lengths, using a key monomer with orthogonal groups. Deprotection or activation allowed stepwise coupling to produce the dimer, trimer, and tetramer, while convergent coupling of appropriately substituted trimers produced the hexamer. The placement of alkoxy side chains renders these oligomers soluble in common organic solvents permitting solution characterization. Absorption and emission spectra of the trimer, tetramer, and hexamer are provided.

  DOI：

  10.1021/ol0352254

文献信息

• Apolar ortho-phenylene ethynylene oligomers: conformational ordering without intermolecular aggregation
  作者：Jing Jiang、Morris M. Slutsky、Ticora V. Jones、Gregory N. Tew

  DOI：10.1039/b9nj00200f

  日期：——

  This paper describes the characterization of solvent induced folding behavior for non-polar (NP) alkoxy substituted ortho-phenylene ethynylene (o-PE) oligomers. Oligomers of lengths up to nine units have been shown to adopt helical conformations in heptane by NMR and CD spectroscopy, while chloroform promotes extended conformations. Surprisingly, the molar ellipticity values found in heptane for these oligomers are very small compared to other literature values of meta-phenylene ethynylene (m-PE) folded systems; however, comparable molar ellipticity values were found for a closed macrocyclic o-PE suggesting the weak ellipticity is a molecular-feature rather than a quality of folding indicator.

  本文描述了非极性 (NP) 烷氧基取代的邻亚苯基乙炔基 (o-PE) 低聚物的溶剂诱导折叠行为的表征。通过核磁共振和圆二色光谱法显示，长度最多为九个单元的低聚物在庚烷中采用螺旋构象，而氯仿则促进延伸构象。令人惊讶的是，与间亚苯基乙炔（m-PE）折叠系统的其他文献值相比，在庚烷中发现的这些低聚物的摩尔椭圆率值非常小；然而，对于闭合大环o-PE，发现了类似的摩尔椭圆率值，这表明弱椭圆率是一种分子特征，而不是折叠指标的质量。