(E)-1-(trimethylsilyl)-4-(4-fluorophenyl)but-3-en-1-yne | 1346459-92-4

• 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: (E)-1-(trimethylsilyl)-4-(4-fluorophenyl)but-3-en-1-yne
• 英文别名: (E)-1-(4-fluorophenyl)-4-trimethylsilyl-1-buten-3-yne；(E)-4-(4-fluorophenyl)-1-(trimethylsilyl)but-3-en-1-yne；[(E)-4-(4-fluorophenyl)but-3-en-1-ynyl]-trimethylsilane
• CAS: 1346459-92-4
• 化学式: C₁₃H₁₅FSi
• 分子量: 218.346
• InChiKey: XPFAHQAVFIBHPY-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  (E)-1-(trimethylsilyl)-4-(4-fluorophenyl)but-3-en-1-yne 在 二乙基氢化铝 作用下， 以 正庚烷 为溶剂， 反应 24.0h， 以59%的产率得到5-(4'-fluorophenyl)-2-[(E)-2-(4''-fluorophenyl)eth-1-enyl]-1,3-bis(trimethylsilyl)benzene
  参考文献：
  名称：

  Dialkylaluminum Hydride-Promoted Cyclodimerization of Silylated 1,3-Enynes via Skeletal Rearrangement

  摘要：

  The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regiolsomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism Involving sequential hydroalumination, alkene isomerization, carboalumination, carbon-carbon bond cleavage, and retro-hydroalumination.

  DOI：

  10.1021/ol202601s
• 作为产物：
  描述：

  1-(2,2-二溴乙烯基)-4-氟苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 亚磷酸二乙酯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 5.0h， 生成 (E)-1-(trimethylsilyl)-4-(4-fluorophenyl)but-3-en-1-yne
  参考文献：
  名称：

  Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand

  摘要：

  DOI：

  10.1021/acs.orglett.1c02140

文献信息

• Microwave-Accelerated Ru-Catalyzed Hydrovinylation of Alkynes and Enynes: A Straightforward Approach toward 1,3-Dienes and 1,3,5-Trienes
  作者：Tobias Schabel、Bernd Plietker

  DOI：10.1002/chem.201300790

  日期：2013.5.27

  dirty! Microwave heating was found to have a significant effect on the Ru‐catalyzed hydrovinylations of alkynes. A broad range of different terminal alkynes were coupled to methyl acrylate within just 30 min in good to excellent yields (see scheme). This new protocol was transferred to the hydrovinylation of enynes as novel coupling partners in CH‐activation chemistry giving different 1,3,5‐trienes

  快速，但不脏！发现微波加热对Ru催化的炔烃氢化乙烯基化有显着影响。在短短30分钟之内即可将各种不同的末端炔烃与丙烯酸甲酯偶联，获得良好至优异的收率（参见方案）。这个新的协议转移到烯炔在C新颖偶联伴侣的hydrovinylation 给予不同的1,3,5-三烯作为唯一的产品H-激活化学。
• <i>Z</i>-Selective (Cross-)Dimerization of Terminal Alkynes Catalyzed by an Iron Complex
  作者：Orestes Rivada-Wheelaghan、Subrata Chakraborty、Linda J. W. Shimon、Yehoshoa Ben-David、David Milstein

  DOI：10.1002/anie.201601382

  日期：2016.6.6

  Efficient iron‐catalyzed homocoupling of terminal alkynes and cross‐dimerization of aryl acetylenes with trimethylsilylacetylene is reported. The complex [Fe(H)(BH4)(iPr‐PNP)] (1) catalyzed the (cross‐)dimerization of alkynes at room temperature, with no need for a base or other additives, to give the corresponding dimerized products with Z selectivity in excellent yields (79–99 %).

  据报道，有效的铁催化末端炔烃的均偶联和芳基乙炔与三甲基甲硅烷基乙炔的交叉二聚。络合物[Fe（H）（BH 4）（i Pr-PNP）]（1）在室温下催化炔烃的（交叉）二聚，无需碱或其他添加剂，即可得到相应的二聚产物与ž在良好的产率（79-99％）的选择性。
• Microwave irradiated Pd-catalyzed C(sp)–H activation and cross-coupling with styryltrifluoroborates
  作者：Mohammad Al-Masum、Wejdan Shaban

  DOI：10.1016/j.tetlet.2015.01.107

  日期：2015.3

  Effective catalytic effect of PdCl2(d(t)bpf) on the C-H activation of alkynes and its ability to overcome the limitations of styryltrifluoroborates in cross-coupling reactions by avoiding the effects of the C-X bond on starting materials is developed. (C) 2015 Elsevier Ltd. All rights reserved.
• Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand
  作者：Jiangui Zhao、Xueli Zheng、Shaokun Tao、Yuxin Zhu、Jiwei Yi、Songbai Tang、Ruixiang Li、Hua Chen、Haiyan Fu、Maolin Yuan

  DOI：10.1021/acs.orglett.1c02140

  日期：2021.8.6
• Dialkylaluminum Hydride-Promoted Cyclodimerization of Silylated 1,3-Enynes via Skeletal Rearrangement
  作者：Hidenori Kinoshita、Tomoyuki Ishikawa、Katsukiyo Miura

  DOI：10.1021/ol202601s

  日期：2011.12.2

  The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regiolsomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism Involving sequential hydroalumination, alkene isomerization, carboalumination, carbon-carbon bond cleavage, and retro-hydroalumination.