(E)-1-(4-tolyl)-4-trimethylsilyl-1-buten-3-yne

• 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-(4-tolyl)-4-trimethylsilyl-1-buten-3-yne
• 英文别名: trimethyl-[(E)-4-(4-methylphenyl)but-3-en-1-ynyl]silane
• 化学式: C₁₄H₁₈Si
• 分子量: 214.382
• InChiKey: BKIRKYLNXQCKON-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-tolyl)-4-trimethylsilyl-1-buten-3-yne 在 甲醇 、 potassium carbonate 作用下， 反应 0.5h， 生成 (E)-1-(but-1-en-3-yn-1-yl)-4-methylbenzene
  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
• 作为产物：
  描述：

  4-methylcinnamic acid 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 5.5h， 生成 (E)-1-(4-tolyl)-4-trimethylsilyl-1-buten-3-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

• (Z)-Selective cross-dimerization of arylacetylenes with silylacetylenes catalyzed by vinylideneruthenium complexes
  作者：Hiroyuki Katayama、Hiroshi Yari、Masaki Tanaka、Fumiyuki Ozawa

  DOI：10.1039/b504436g

  日期：——

  The vinylideneruthenium(II) complexes bearing bulky and basic tertiary phosphine ligands, RuCl2(CCHPh)L2 (L = PPri3, PCy3), serve as good catalyst precursors for (Z)-selective cross-dimerization between arylacetylenes and silylacetylenes in the presence of N-methylpyrrolidine.

  具有体积庞大且基本的三苯基膦配体的乙烯基二羟基铑(II)复合物 RuCL2(CCHPh)L2（L = PPri3, PCy3）在N-甲基吡咯烷的存在下，作为选择性（Z）交叉二聚化的良好催化剂前体，用于芳基乙炔与硅乙炔之间的反应。
• Phosphine-Dependent Selective Cross-Dimerization between Terminal Alkylacetylene and Silylacetylene by Iridium(I) Guanidinate Complex-Phosphine System
  作者：Kenichi Ogata、Shin-ichi Fukuzawa、Oji Oka、Akinori Toyota、Noriyuki Suzuki

  DOI：10.1055/s-0028-1083514

  日期：——

  The new iridium(I)-guanidinate complex served as an efficient catalyst for phosphine-dependent selective cross-dimerization between silylacetylene and terminal alkyl- or arylacetylene. Especially, in case of cross-dimerization between silylacetylene and alkylacetylene, E/Z selectivity of resulting enynes could be controlled by changing phosphine.

  新的铱(I)-氨基酸盐复合物作为一种高效催化剂，促进了硅烷乙炔和末端烷基或芳烃乙炔之间的磷依赖性选择性交叉二聚化。特别是在硅烷乙炔和烷基乙炔之间的交叉二聚化中，最终得到的烯炔的E/Z选择性可以通过更换磷烃来调控。
• <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。
• 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.
• 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.