((4-fluorophenyl)buta-1,3-diyn-1-yl)triisopropylsilane | 920282-76-4

• 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-fluorophenyl)buta-1,3-diyn-1-yl)triisopropylsilane
• 英文别名: [4-(4-Fluorophenyl)buta-1,3-diyn-1-yl]tri(propan-2-yl)silane；4-(4-fluorophenyl)buta-1,3-diynyl-tri(propan-2-yl)silane
• CAS: 920282-76-4
• 化学式: C₁₉H₂₅FSi
• 分子量: 300.491
• InChiKey: RURWFMRMHUXLAY-UHFFFAOYSA-N

物化性质

• 沸点：
  344.9±44.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ((4-fluorophenyl)buta-1,3-diyn-1-yl)triisopropylsilane 在 四丁基氟化铵 作用下， 生成 1-(buta-1,3-diyn-1-yl)-4-fluorobenzene
  参考文献：
  名称：

  Gold-Catalyzed Oxidative Cross-Coupling of Terminal Alkynes: Selective Synthesis of Unsymmetrical 1,3-Diynes

  摘要：

  Gold-catalyzed oxidative cross-coupling of alkynes to unsymmetrical diynes has been achieved for the first time. A N,N-ligand (1,10-Phen) and PhI(OAc)2 were identified as crucial factors to promote this transformation, giving the desired cross-coupled conjugated diynes in excellent heteroselectivity (>10:1), in good to excellent yields, and with large substrate tolerability.

  DOI：

  10.1021/ja5078365
• 作为产物：
  描述：

  triisopropyl((trimethylsilyl)buta-1,3-diyn-1-yl)silane 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 ((4-fluorophenyl)buta-1,3-diyn-1-yl)triisopropylsilane
  参考文献：
  名称：

  Regioselective Trapping of Terminal Di-, Tri-, and Tetraynes with Benzyl Azide

  摘要：

  The reaction of benzyl azide with terminal di-, tri-, and tetraynes appended with a range of functional groups has been explored. Standard reaction conditions for BnN3 catalyzed by CuSO(4)(.)5H(2)O gave alkynyl, butadiynyl, and hexatriynyl triazoles in moderate to good yields. The reaction proceeds regioselectively as determined by the X-ray crystallographic analysis of three derivatives (1c, 1d, and 3c), and no evidence of multiple azide addition to the polyyne framework is observed.

  DOI：

  10.1021/ol062522a

文献信息

• Gold-Catalyzed Oxidative Coupling of Alkynes toward the Synthesis of Cyclic Conjugated Diynes
  作者：Xiaohan Ye、Haihui Peng、Chiyu Wei、Teng Yuan、Lukasz Wojtas、Xiaodong Shi

  DOI：10.1016/j.chempr.2018.07.004

  日期：2018.8

  developed as an efficient approach for the synthesis of challenging cyclic conjugated diynes (CCD). Compared with the classic copper-promoted oxidative coupling reaction of alkynes, this gold-catalyzed process exhibited a faster reaction rate due to rapid reductive elimination from the Au(III) intermediate. This unique reactivity thus allowed a challenging diyne macrocyclization to take place with high

  炔烃的金催化氧化偶联被开发为合成具有挑战性的环状共轭二炔（CCD）的有效方法。与经典的炔烃铜促进的氧化偶联反应相比，由于金（III）中间体的快速还原消除，这种金催化的方法显示出更快的反应速率。因此，这种独特的反应性使得高效的挑战性二炔大环化发生。条件筛选显示[[（n -Bu）4 N] + [Cl-Au-Cl] -盐作为最佳的前催化剂。以中等至良好的产率制备了具有13至28个原子的环大小的大环化合物，这突出了该新策略的广泛底物范围。此外，已经证明了用于无铜点击化学的CCD的合成效用，表明了该策略在生物系统中的潜在应用。
• Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)–C(sp) cross-coupling reactions
  作者：Somsuvra Banerjee、Nitin T. Patil

  DOI：10.1039/c7cc04283c

  日期：——

  Reported herein is the gold-catalyzed alkynylation of terminal alkynes using ethynylbenziodoxolones (EBXs), where EBXs serve a dual role as oxidants as well as alkyne transfer agents to access unsymmetrical 1,3-diynes. Hence, the catalytic system requires no external oxidants and is compatible with a broad range of substrates, including those with polar functional groups such as NH, OH and B(OH)2.

  本文报道的是使用乙炔基苯并恶恶唑酮（EBX）的末端炔烃的金催化炔基化反应，其中EBX担当氧化剂和炔烃转移剂的双重角色，以访问不对称的1,3-二炔。因此，该催化体系不需要外部氧化剂，并且与各种底物兼容，包括具有极性官能团（例如NH，OH和B（OH）2）的底物。
• Transition metal-free coupling of terminal alkynes and hypervalent iodine-based alkyne-transfer reagents to access unsymmetrical 1,3-diynes
  作者：J. Schörgenhumer、M. Waser

  DOI：10.1039/c8ob02375a

  日期：——

  A variety of unsymmetrical 1,3-diynes can easily be accessed in good yields under catalyst- and transition metal-free conditions by reacting terminal alkynes with hypervalent iodine-based electrophilic alkyne-transfer reagents.

  通过使末端炔烃与高价碘基亲电炔烃转移试剂反应，可以轻松地在无催化剂和无过渡金属的条件下以高收率轻松获得各种不对称的1,3-二炔。
• Selective synthesis of boron-substituted enynes<i>via</i>a one-pot diboration/protodeboration sequence
  作者：Jakub Szyling、Aleksandra Szymańska、Jędrzej Walkowiak

  DOI：10.1039/d3cc02695g

  日期：——

  access enynylboronates via a Pt-catalyzed diboration/protodeboration strategy has been developed. The reaction is suitable for various silylsubstituted symmetrical and unsymmetrical 1,3-diynes, leading to π-conjugated organoboron compounds with excellent regio- and stereoselectivity.

  开发了一种通过Pt 催化二硼化/原脱硼策略获取烯炔基硼酸盐的高效且简便的一锅法方案。该反应适用于各种甲硅烷基取代的对称和不对称1,3-二炔，产生具有优异区域和立体选择性的π-共轭有机硼化合物。
• Reactions of Terminal Polyynes with Benzyl Azide
  作者：Thanh Luu、Boris J. Medos、Erin R. Graham、Danielle M. Vallee、Robert McDonald、Michael J. Ferguson、Rik R. Tykwinski

  DOI：10.1021/jo101870y

  日期：2010.12.17

  Terminal di-, tri-, tetra-, and pentaynes substituted with a variety of functional groups react with benzyl azide in the presence of CuSO4 center dot 5H(2)O and ascorbic acid to give derivatives of 4-ethynyl-, 4-butadiynyl-, 4-hexatriynyl-, and 4-octatetraynyl-,2,3-triazoles in moderate to good yields. These reactions appear to proceed regioselectively, and functionalization occurs exclusively at the terminal alkyne moiety. As well, no evidence of multiple azide additions to the polyyne framework is observed. X-ray crystallographic analysis of nine derivatives is used to document the regioselectivity of the reaction as well as outline structural characteristics of the 1,2,3-triazole products.