5-(3-hydroxy-3-methylbutynyl)-5'-(trimethylsilyl)ethynyl-2,2'-bipyridine | 794529-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(3-hydroxy-3-methylbutynyl)-5'-(trimethylsilyl)ethynyl-2,2'-bipyridine
• 英文别名: 3-Butyn-2-ol, 2-methyl-4-[5'-[(trimethylsilyl)ethynyl][2,2'-bipyridin]-5-yl]-；2-methyl-4-[6-[5-(2-trimethylsilylethynyl)pyridin-2-yl]pyridin-3-yl]but-3-yn-2-ol
• CAS: 794529-14-9
• 化学式: C₂₀H₂₂N₂OSi
• 分子量: 334.493
• InChiKey: FSAOTGPTFRFWNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3-hydroxy-3-methylbutynyl)-5'-(trimethylsilyl)ethynyl-2,2'-bipyridine 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以88%的产率得到5-ethynyl-5'-(trimethylsilyl)ethynyl-2,2'-bipyridine
  参考文献：
  名称：

  Oligomeric Ligands Incorporating Multiple 5,5‘-Diethynyl-2,2‘-bipyridine Moieties Bridged and End-Capped by 3,4-Dibutylthiophene Units

  摘要：

  In this work, we detail the synthesis and photophysical properties of a series of soluble polybipyridine ligands comprising one to five bipyridine units sandwiched between rigid carbon-carbon triple bonds substituted by 3,4-dibutylthiophene repeating units. The dual Sonogashira coupling reaction of 5,5'-dibromo-2,2'-bipyridine with TMS- and (CH3)(2)C(OH)-protected acetylene allows the synthesis of a dissymmetrically functionalized building block which was selectively deprotected at either the TMS or 2-hydroxyprop-2-yl site. Various combinations allow the interconnection of the terminal alkyne to 3,4-dibutyl-2,5-diiodothiophene or 3,4-dibutyl-2-iodothiophene leading to hipyridine frameworks bearing two acetylene-protected groups or one acetylenethiophene/one acetylene-protected function. It is possible therefore to construct dimeric to pentameric bipyridine ligands where the chelating subunit is bridged by a 3,4-dibutyl-2,5-diethynylthiophene spacer and endcapped by a 3,4-dibutyl-2-ethynylthiophene stopper. All cross-coupling reactions are promoted with palladium(0) tetrakistriphenylphosphine under mild conditions. Spectroscopic data for the new oligomers are discussed in terms of the extent of pi-electron conjugation. Upon increasing the number of pi-electrons from 24 to 104, there is a progressive lowering in the energy of absorption and fluorescence transitions, while the emission quantum yields remain essentially constant. The LUMO levels of these large molecules, estimated by cyclic voltammetry, lie in the range -3.06 to -3.18 eV.

  DOI：

  10.1021/jo048435i
• 作为产物：
  描述：

  5,5'-二溴-2,2'-联吡啶 、 2-甲基-3-丁炔-2-醇 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以33%的产率得到5-(3-hydroxy-3-methylbutynyl)-5'-(trimethylsilyl)ethynyl-2,2'-bipyridine
  参考文献：
  名称：

  从噻吩和炔烃键逐步合成共轭桥联联吡啶配体

  摘要：

  5,5'-二溴-2,2'-联吡啶与 TMS 和 CMe 2 OH 保护的乙炔的双重 Sonogashira 偶联反应允许合成从 TMS 或 2-羟基-丙二醇选择性脱保护的双对称官能化结构单元-2-基位点。各种组合允许末端炔烃与 3,4-二丁基-2-碘噻吩或 3,4-二丁基-2,5-二碘噻吩互连，从而形成带有两个乙炔基噻吩单元或一个噻吩/一个乙炔官能团的联吡啶骨架。可以构建双位或三位联吡啶配体，其中螯合亚基由 3,4-二丁基-2,5-二乙炔基噻吩间隔物桥接，并由 3,4-二丁基-2-乙炔基噻吩终止剂封端。

  DOI：

  10.1055/s-2005-861847

文献信息

• Oligomeric Ligands Incorporating Multiple 5,5‘-Diethynyl-2,2‘-bipyridine Moieties Bridged and End-Capped by 3,4-Dibutylthiophene Units
  作者：Sébastien Goeb、Antoinette De Nicola、Raymond Ziessel

  DOI：10.1021/jo048435i

  日期：2005.3.1

  In this work, we detail the synthesis and photophysical properties of a series of soluble polybipyridine ligands comprising one to five bipyridine units sandwiched between rigid carbon-carbon triple bonds substituted by 3,4-dibutylthiophene repeating units. The dual Sonogashira coupling reaction of 5,5'-dibromo-2,2'-bipyridine with TMS- and (CH3)(2)C(OH)-protected acetylene allows the synthesis of a dissymmetrically functionalized building block which was selectively deprotected at either the TMS or 2-hydroxyprop-2-yl site. Various combinations allow the interconnection of the terminal alkyne to 3,4-dibutyl-2,5-diiodothiophene or 3,4-dibutyl-2-iodothiophene leading to hipyridine frameworks bearing two acetylene-protected groups or one acetylenethiophene/one acetylene-protected function. It is possible therefore to construct dimeric to pentameric bipyridine ligands where the chelating subunit is bridged by a 3,4-dibutyl-2,5-diethynylthiophene spacer and endcapped by a 3,4-dibutyl-2-ethynylthiophene stopper. All cross-coupling reactions are promoted with palladium(0) tetrakistriphenylphosphine under mild conditions. Spectroscopic data for the new oligomers are discussed in terms of the extent of pi-electron conjugation. Upon increasing the number of pi-electrons from 24 to 104, there is a progressive lowering in the energy of absorption and fluorescence transitions, while the emission quantum yields remain essentially constant. The LUMO levels of these large molecules, estimated by cyclic voltammetry, lie in the range -3.06 to -3.18 eV.
• Stepwise Synthesis of Conjugatively Bridged Bipyridine Ligands from Thiophene and Alkyne Linkages
  作者：Raymond Ziessel、Sébastien Goeb、Antoinette De Nicola

  DOI：10.1055/s-2005-861847

  日期：——

  coupling reaction of 5,5'-dibromo-2,2'-bipyridine with TMS and CMe 2 OH protected acetylene allows the synthesis of a disymmetrically functionalized building block which was selectively deprotected from the TMS or the 2-hydroxy-prop-2-yl site. Various combinations allow the interconnection of the terminal alkyne to 3,4-dibutyl-2-iodothiophene or 3,4-dibutyl-2,5-diiodothiophene leading to bipyridine frameworks

  5,5'-二溴-2,2'-联吡啶与 TMS 和 CMe 2 OH 保护的乙炔的双重 Sonogashira 偶联反应允许合成从 TMS 或 2-羟基-丙二醇选择性脱保护的双对称官能化结构单元-2-基位点。各种组合允许末端炔烃与 3,4-二丁基-2-碘噻吩或 3,4-二丁基-2,5-二碘噻吩互连，从而形成带有两个乙炔基噻吩单元或一个噻吩/一个乙炔官能团的联吡啶骨架。可以构建双位或三位联吡啶配体，其中螯合亚基由 3,4-二丁基-2,5-二乙炔基噻吩间隔物桥接，并由 3,4-二丁基-2-乙炔基噻吩终止剂封端。