Trimethyl-(4-thiophen-3-yl-buta-1,3-diynyl)-silane | 848641-96-3

• 分子结构分类: 有机化合物 - 有机金属化合物
• 英文名称: Trimethyl-(4-thiophen-3-yl-buta-1,3-diynyl)-silane
• 英文别名: trimethyl(4-thiophen-3-ylbuta-1,3-diynyl)silane
• CAS: 848641-96-3
• 化学式: C₁₁H₁₂SSi
• 分子量: 204.368
• InChiKey: PDNMQIDOTSWRGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Trimethyl-(4-thiophen-3-yl-buta-1,3-diynyl)-silane 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 3-(buta-1,3-diyn-1-yl)thiophene
  参考文献：
  名称：

  Synthesis of indenothiophenone derivatives by cycloaromatization of non-conjugated thienyl tetraynes

  摘要：

  Non-conjugated thienyl tetrayne derivatives 1-3 are prepared as novel building block for the construction of indenothiophenone derivatives. Oxidation of 1-3, followed by cycloaromatization of the corresponding ketone derivatives 13-15 proceeds smoothly to afford indenothiophenone derivatives 16-21 in good yields. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.005
• 作为产物：
  描述：

  3-溴噻吩 、 1-trimethylsilyl-4-(tributylstannino)buta-1,3-diyne 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 甲苯 为溶剂， 以89%的产率得到Trimethyl-(4-thiophen-3-yl-buta-1,3-diynyl)-silane
  参考文献：
  名称：

  Synthesis of indenothiophenone derivatives by cycloaromatization of non-conjugated thienyl tetraynes

  摘要：

  Non-conjugated thienyl tetrayne derivatives 1-3 are prepared as novel building block for the construction of indenothiophenone derivatives. Oxidation of 1-3, followed by cycloaromatization of the corresponding ketone derivatives 13-15 proceeds smoothly to afford indenothiophenone derivatives 16-21 in good yields. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.005

文献信息

• Ligand-Controlled Regiodivergent Nickel-Catalyzed Hydrocyanation of Silyl-Substituted 1,3-Diynes
  作者：Feilong Sun、Chengxi Yang、Jie Ni、Gui-Juan Cheng、Xianjie Fang

  DOI：10.1021/acs.orglett.1c01262

  日期：2021.5.21

  A regiodivergent nickel-catalyzed hydrocyanation of 1-aryl-4-silyl-1,3-diynes is reported. When appropriate bisphosphine and phosphine–phosphite ligands are applied, the same starting materials can be converted into two different enynyl nitriles with good yields and high regioselectivities. The DFT calculations unveiled that the structural features of different ligands bring divergent alkyne insertion

  报道了1-芳基-4-甲硅烷基-1，3-二炔的区域发散性镍催化的氢氰化。当使用适当的双膦和膦-亚磷酸酯配体时，相同的原料可以高产率和高区域选择性转化为两种不同的烯丙基腈。DFT计算揭示了不同配体的结构特征带来了不同的炔烃插入模式，进而导致不同的区域选择性。此外，已经通过数个下游转化证明了含氰基的1，3-烯炔的合成值。
• Cobalt-Catalyzed Regio- and Stereoselective Hydrosilylation of 1,3-Diynes To Access Silyl-Functionalized 1,3-Enynes
  作者：Hui Leng Sang、Yongyi Hu、Shaozhong Ge

  DOI：10.1021/acs.orglett.9b01836

  日期：2019.7.5

  A regio- and stereoselective hydrosilylation of 1,3-diynes has been developed relying on catalysts generated from bench-stable Co(acac)2 and dppp ligand. A variety of symmetrical and unsymmetrical 1,3-diynes undergo this transformation, yielding the corresponding silyl-functionalized 1,3-enynes in high yields with excellent regioselectivity. Gram-scale reactions and further transformations of the silyl-containing

  1，3-二炔的区域和立体选择性氢化硅烷化已经开发出来，它依赖于稳定的Co（acac）2和dppp配体产生的催化剂。各种对称和不对称的1,3-二炔都经历了这种转变，以高收率和良好的区域选择性产生了相应的甲硅烷基官能化的1,3-烯炔。含甲硅烷基的1,3-烯炔产物的克级反应和进一步转化突出了这种1,3-二炔共催化氢化硅烷化反应的合成效用。
• Cobalt-Catalyzed Regiodivergent Stereoselective Hydroboration of 1,3-Diynes To Access Boryl-Functionalized Enynes
  作者：Hui Leng Sang、Caizhi Wu、Guan Ge Darren Phua、Shaozhong Ge

  DOI：10.1021/acscatal.9b03139

  日期：2019.11.1

  We report a regiodivergent and stereoselective hydroboration of 1,3-diynes with pinacolborane (HBpin) in the presence of cobalt catalysts generated in situ from bench-stable Co(acac)(2) and bisphosphine ligands. These cobalt catalysts were activated by the reactions with HBpin. A range of unsymmetrical and symmetrical 1,3-diynes reacted smoothly with HBpin in the presence of Co(acac)(2)/xantphos to selectively afford enynylboronate products with boron addition to the internal carbon of the 1,3-diyne unit. However, these 1,3-diynes reacted in the presence of Co(acac)(2)/dppf to form enynylboronate products with boron addition to the external carbon of the 1,3-diyne unit. These hydroboration reactions show good functional group compatibility and can be readily scaled up to gram-scales without using a drybox. Deuterium-labeling experiments suggest a cis-addition of HBpin to the less-hindered triple bond of 1,3-diynes. Furthermore, the comparison of the regioselectivity between cobalt-catalyzed hydrosilylation and hydroboration reactions of the same 1,3-diyne substrate suggests that Co(acac)(2)/xantphos-catalyzed regioselective 1,3-diyne hydroboration proceeds through a cobalt-hydride intermediate while Co(acac)(2)/dppf-catalyzed 1,3-diyne hydroboration proceed through a cobalt boryl intermediate.