4-<2-<(Trimethylsilyl)ethynyl>phenyl>-3-butyn-1-ol | 159305-97-2

• 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: 4-<2-<(Trimethylsilyl)ethynyl>phenyl>-3-butyn-1-ol
• 英文别名: 4-(2-(2-(trimethylsilyl)ethynyl)phenyl)but-3-yn-1-ol；4-[2-(2-Trimethylsilylethynyl)phenyl]but-3-yn-1-ol
• CAS: 159305-97-2
• 化学式: C₁₅H₁₈OSi
• 分子量: 242.393
• InChiKey: KHQIRKDHHPCEIA-UHFFFAOYSA-N

物化性质

• 沸点：
  343.8±42.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-<2-<(Trimethylsilyl)ethynyl>phenyl>-3-butyn-1-ol 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 4-(2-Ethynylphenyl)-3-butynyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

  摘要：

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.

  DOI：

  10.1021/jo00104a053
• 作为产物：
  描述：

  1,2-二碘苯 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 0.5h， 生成 4-<2-<(Trimethylsilyl)ethynyl>phenyl>-3-butyn-1-ol
  参考文献：
  名称：

  Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

  摘要：

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.

  DOI：

  10.1021/jo00104a053

文献信息

• Functionalization of Pristine Graphene with Conjugated Polymers through Diradical Addition and Propagation
  作者：Xiaowei Ma、Fei Li、Youfu Wang、Aiguo Hu

  DOI：10.1002/asia.201200520

  日期：2012.11

  Hanging on: Pristine graphene was grafted with conjugated polymers through addition and propagation of diradicals generated from Bergman cyclization of enediyne‐containing dendrimers. The surface functionalization was confirmed with TGA, FTIR and Raman spectroscopy, and AFM analysis. The sp2 network of graphene is only slightly destroyed, as revealed by conductivity measurements.

  悬而未决：通过添加和扩散由含烯二炔树枝状聚合物的Bergman环化反应生成的双基，将原始石墨烯与共轭聚合物接枝。通过TGA，FTIR和拉曼光谱以及AFM分析确认了表面功能化。如电导率测量所揭示的，石墨烯的sp 2网络仅被轻微破坏。
• Covalent surface functionalization of multiwalled carbon nanotubes through bergman cyclization of enediyne-containing dendrimers
  作者：Jianguo Ma、Sheng Deng、Xin Cheng、Wei Wei、Aiguo Hu

  DOI：10.1002/pola.24834

  日期：2011.9.15

  A method for covalent functionalization of multiwalled carbon nanotubes (MWCNTs) was developed using the free radicals generated through Bergman cyclization of enediyne‐containing compounds. Four enediyne‐bearing Frechet type dendrimers were synthesized in good quantities and characterized. Then, the enediyne‐containing molecules were reacted with MWCNTs in N‐methyl‐2‐pyrrolidinone at 206 °C under

  利用含烯二炔化合物的Bergman环化作用产生的自由基，开发了一种多壁碳纳米管（MWCNT）的共价官能化方法。大量合成并表征了四种含烯二炔的Frechet型树状聚合物。然后，使含烯二炔的分子与N中的MWCNTs反应氮下于206°C时的2-甲基-2-吡咯烷酮。通过热重分析，紫外可见光谱，傅立叶变换红外光谱，拉曼光谱和透射电子显微镜对所得产物的结构和形态进行表征。树枝状聚合物官能化的MWCNT在常见的有机溶剂和聚合物溶液中显示出良好的溶解性/分散性。它们通过与聚己内酯电纺丝用于聚合物复合材料的形成。结果证实了MWCNT的表面功能化。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年
• Synthesis of dendronized polymers through bergman cyclization of enediyne-containing Frechet-type dendrimers
  作者：Jianguo Ma、Xiaowei Ma、Sheng Deng、Fei Li、Aiguo Hu

  DOI：10.1002/pola.24556

  日期：2011.3.15

  article, dendronized polymers with rigid backbones were synthesized from enediyne‐containing Frechet‐type dendrimers. Two generations of dendrimers were conically incorporated with 3‐(2‐(2‐(trimethylsilyl)ethynyl)phenyl)prop‐2‐yn‐1‐ol. The trimethylsilyl protection groups of enediyne units were subsequently removed, and two types of brush polymers with rigid conjugated backbone were prepared through Bergman

  在这篇文章中，具有刚性骨架的树枝状聚合物是由含烯二炔的Frechet型树枝状聚合物合成的。将两代树枝状聚合物与3-（2-（2-（3-（三甲基甲硅烷基）乙炔基）苯基）prop-2-yn-1-ol圆锥形结合。随后除去烯二炔单元的三甲基甲硅烷基保护基，并通过在真空下在升高的温度下通过Bergman环化聚合反应制备具有刚性共轭主链的两种类型的刷聚合物。用GPC，IR，UV-vis和NMR光谱对树枝状聚合物进行了表征。此外，通过原子力显微镜揭示了树枝状聚合物的形态。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年
• Synthesis of Novel “Rod−Coil” Brush Polymers with Conjugated Backbones through Bergman Cyclization
  作者：Xin Cheng、Jianguo Ma、Jian Zhi、Xi Yang、Aiguo Hu

  DOI：10.1021/ma902176j

  日期：2010.1.26

  This work reports synthesis of “rod−coil” brush polymers with rigid conjugated backbone. “Grafting through” strategy was employed via combination of ring-opening polymerization (ROP) and Bergman cyclization polymerization. Enediyne-containing macromonomers were first synthesized through ROP of caprolactone with dual-functional initiators conceiving free hydroxy groups and dialkynylbenzene moieties

  这项工作报告了具有刚性共轭骨架的“杆-圈”刷聚合物的合成。通过开环聚合（ROP）和Bergman环化聚合的组合采用“嫁接”策略。首先通过己内酯与具有游离羟基和二炔基苯部分的双功能引发剂进行ROP合成含烯二炔的大分子单体。在保护PCL链的末端游离羟基并除去烯二炔单元的三甲基甲硅烷基保护基之后，将大分子单体在真空下进行热Bergman环化。使用GPC和NMR，IR和UV-vis光谱对获得的刷状聚合物进行了表征。根据NMR分析，共轭的主链显示为萘和茚基亚甲基的共聚物。
• Platinum- and Ruthenium-Catalyzed Aromatization of Enediynes via Intramolecular­ Nucleophilic Additions
  作者：Rai-Shung Liu、Bhanu Taduri、Arjan Odedra、Cheng-Yi Lung

  DOI：10.1055/s-2007-983739

  日期：2007.7

  Catalytic cyclization of enediynes via intramolecular nucleophilic addition was achieved with TpRuPPh3(MeCN)2PF6 and platinum dichloride, giving naphthalene-fused 2,3-dihydrofurans and -pyrroles in good yields. On the basis of experimental results, the mechanism is proposed to involve nucleophilic addition to a π-alkyne intermediate, followed by alkyne insertion.

  利用 TpRuPPh3(MeCN)2PF6 和二氯化铂通过分子内亲核加成实现了烯炔类化合物的催化环化，以良好的产率得到了萘融合的 2,3- 二氢呋喃和吡咯。在实验结果的基础上，提出了亲核加成Ï-炔中间体，然后插入炔的机理。