2-ethynyl-6-(2-(trimethylsilyl)ethynyl)pyridine | 496840-15-4

• 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: 2-ethynyl-6-(2-(trimethylsilyl)ethynyl)pyridine
• 英文别名: 2-ethynyl-6-[2-(trimethylsilyl)ethynyl]pyridine；2-ethynyl-6-(trimethylsilylethynyl)pyridine；2-(6-Ethynylpyridin-2-yl)ethynyl-trimethylsilane
• CAS: 496840-15-4
• 化学式: C₁₂H₁₃NSi
• 分子量: 199.327
• InChiKey: DGGOHHRQHWACJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethynyl-6-(2-(trimethylsilyl)ethynyl)pyridine 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 33.0h， 生成
  参考文献：
  名称：

  Metal-Assisted Assembly of Pyridine-Containing Arylene Ethynylene Strands to Enantiopure Double Helicates

  摘要：

  Pyridine-containing arylene ethynylene strands were connected to the 2- and 2'-positions of (R)- and (S)-1,1'-binaphthyl templates. The arylene ethynylene moieties underwent intramolecular coordination with Ag(I) or Cu(I) ion to afford enantiopure double helicates. The double-helical structure was elucidated on the basis of circular dichroic (CD) spectra. The importance of intramolecular complexation of the double strands for the helicate formation was confirmed by comparison with a ligand bearing a single strand. Connection of the strands through an ether linkage enabled a sorting out of the Cotton effect induced by double-helical arylene ethynylene moieties. The CD exciton chirality method unambiguously proved that the termini of the strands approach each other upon complexation and that the sense of the induced helicity is the same as predicted by molecular modeling.

  DOI：

  10.1021/ja048327d
• 作为产物：
  描述：

  2,6-二溴吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 乙基溴化镁 、 四丁基氟化铵 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2-ethynyl-6-(2-(trimethylsilyl)ethynyl)pyridine
  参考文献：
  名称：

  铜（I）离子介导的低聚（2-乙炔基吡啶）三链螺旋自组装：合成、结构和性质

  摘要：

  低聚（2-乙炔基吡啶）（L1-L8）与铜（I）离子的反应顺利进行，以良好的产率得到三、四和五核三链螺旋（CL1-CL8）。如果使用手性配体，则在固态下可实现具有一种特定手性的手性螺旋的立体选择性自组装。在溶液中也观察到铜 (I) 螺旋的外消旋化。

  DOI：

  10.1246/bcsj.76.709

文献信息

• Design of Glycosyltransferase Inhibitors: Pyridine as a Pyrophosphate Surrogate
  作者：Shuai Wang、Jose A. Cuesta-Seijo、Dominique Lafont、Monica M. Palcic、Sébastien Vidal

  DOI：10.1002/chem.201301871

  日期：2013.11.4

  series of ten glycosyltransferase inhibitors has been designed and synthesized by using pyridine as a pyrophosphate surrogate. The series was prepared by conjugation of carbohydrate, pyridine, and nucleoside building blocks by using a combination of glycosylation, the Staudinger–Vilarrasa amide‐bond formation, and azide–alkyne click chemistry. The compounds were evaluated as inhibitors of five metal‐dependent

  通过使用吡啶作为焦磷酸盐替代物，已经设计并合成了一系列十种糖基转移酶抑制剂。该系列是通过结合糖基化，Staudinger-Vilarrasa酰胺键形成和叠氮化物-炔烃点击化学反应，结合碳水化合物，吡啶和核苷结构单元而制备的。该化合物被评估为五种金属依赖性半乳糖基转移酶的抑制剂。三种酶在一种酶的活性位点复合的抑制剂的晶体学分析证实，吡啶部分螯合了Mn 2+离子，导致其原始位置略微移位（2Å）。与天然尿苷二磷酸（UDP）-Gal底物相比，碳水化合物的头基占据的位置不同，与酶的相互作用很小。
• Foldamer-based helicate displaying reversible switching between two distinct conformers
  作者：Hae-Geun Jeon、Hyun Kyung Lee、Seungwon Lee、Kyu-Sung Jeong

  DOI：10.1039/c8cc02758g

  日期：——

  A new double-stranded dinuclear helicate that displays conformational switching in response to temperature was prepared by self-assembly of an aromatic helical foldamer and dichloropalladium(II). The relative populations of the two helicate conformers, syn–anti and syn–syn, were demonstrated to be reversibly modulated through temperature control.

  通过芳族螺旋折叠剂和二氯钯（II）的自组装制备了一种新的显示响应温度的构象转换的双链双核螺旋体。已证明通过温度控制可逆地调节了两个螺旋构象异构体syn - anti和syn - syn的相对种群。
• Endohedrally functionalised porous organic cages
  作者：Alexandre Burgun、Peter Valente、Jack D. Evans、David M. Huang、Christopher J. Sumby、Christian J. Doonan

  DOI：10.1039/c6cc04423a

  日期：——

  The synthesis and characterisation of two novel, functionalised porous organic cages are presented. We demontrate that a step-wise approach to the synthesis of these robust C-C bonded cages allows for...

  介绍了两种新颖的，功能化的多孔有机笼的合成和表征。我们取消了逐步合成这些坚固的CC键合保持架的方法，从而实现了...
• Synthesis of oligo(2-ethynylpyridines): novel building blocks for supramolecular systems
  作者：Tomikazu Kawano、Takahiro Kato、Chong-Xu Du、Ikuo Ueda

  DOI：10.1016/s0040-4039(02)01542-3

  日期：2002.9

  New oligo(2-ethynylpyridines) 1 are synthesized as novel building blocks for the construction of supramolecular systems by the coupling reaction of the novel dibromopyridines 2 with ethynylpyridines 3. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Dipole-Promoted and Size-Dependent Cooperativity between Pyridyl-Containing Triazolophanes and Halides Leads to Persistent Sandwich Complexes with Iodide
  作者：Yongjun Li、Maren Pink、Jonathan A. Karty、Amar H. Flood

  DOI：10.1021/ja8077329

  日期：2008.12.24

  Triazolophanes that incorporate pyridyl subunits in place of phenylenes show a heightened propensity to form 2:1 sandwich complexes with halides. Persistent iodide-based sandwiches are observed. Binding constants confirm that the inward-facing electron pairs on the pyridyls destabilize the 1:1 complexes with halides. The H-1 NMR spectra verify that the sandwich complexes have two TT-stacked triazolophanes rotated to allow registration between opposite dipoles on the pyridyls (directed inward) and triazoles (directed outward). These dipolar interactions cooperate to lower the pyridyl-based repulsions, therefore, increasing K-2. Modest cooperative effects are observed for the snugly fitting F-, Cl-, and Br- halides while the too-large l(-) shows highly positive cooperativity.