1-(2-methyl-5-(phenyl(triethylsilyl)methyl)furan-3-yl)ethanone | 1402404-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-methyl-5-(phenyl(triethylsilyl)methyl)furan-3-yl)ethanone
• 英文别名: 1-[2-Methyl-5-[phenyl(triethylsilyl)methyl]furan-3-yl]ethanone
• CAS: 1402404-44-7
• 化学式: C₂₀H₂₈O₂Si
• 分子量: 328.527
• InChiKey: FDKJEZSNZKNYKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯丙炔醛 在 哌啶 、 1,3-双(2,6-二-异丙基苯基)咪唑-2-亚基金(I)氯化物 、 magnesium sulfate 、 溶剂黄146 、 Selectfluor 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 12.0h， 生成 1-(2-methyl-5-(phenyl(triethylsilyl)methyl)furan-3-yl)ethanone
  参考文献：
  名称：

  NHC–AuCl/Selectfluor: A Highly Efficient Catalytic System for Carbene-Transfer Reactions

  摘要：

  The combination of NHC-gold complex and Selectfluor has been found to be a highly efficient catalyst system for carbene-transfer reactions, with a turnover number (TON) up to 990000 and a turnover frequency (TOF) up to 82500 h(-1).

  DOI：

  10.1021/ol502018d

文献信息

• Catalytic Generation of Zinc Carbenes from Alkynes: Zinc-Catalyzed Cyclopropanation and SiH Bond Insertion Reactions
  作者：Rubén Vicente、Jesús González、Lorena Riesgo、Javier González、Luis A. López

  DOI：10.1002/anie.201203914

  日期：2012.8.6

  Think zinc: Synthetically relevant zinc(II) carbenes are catalytically generated from alkynes (see scheme). This new approach allows zinc‐catalyzed cyclopropanation and SiH bond insertion reactions to generate the corresponding cyclopropylfurans or silane derivatives. The structure of the key carbene intermediate was studied using theoretical methods.

  想想锌：与合成相关的锌（II）卡宾是由炔烃催化生成的（请参阅方案）。这种新方法允许锌催化的环丙烷化和SiH键插入反应生成相应的环丙基呋喃或硅烷衍生物。用理论方法研究了关键卡宾中间体的结构。
• Zinc-Catalyzed Functionalization of SiH Bonds with 2-Furyl Carbenoids through Three-Component Coupling
  作者：Sergio Mata、Luis A. López、Rubén Vicente

  DOI：10.1002/chem.201501155

  日期：2015.6.15

  A three‐component coupling of alk‐2‐ynals, 1,3‐dicarbonyls and silanes is reported. ZnCl2 serves as an inexpensive and low‐toxic catalyst for the overall transformation, which involves Knoevenagel condensation, cyclization, and carbene SiH bond insertion. The process takes place with high atom economy in the absence of organic solvents and shows a broad scope. This reaction is also applicable to the

  据报道，烷基-2-醛，1,3-二羰基和硅烷三组分偶联。ZnCl 2是一种廉价且低毒的催化剂，可用于整个转化过程，涉及Knoevenagel缩合，环化和卡宾SiH键插入。该方法在没有有机溶剂的情况下以高原子经济性进行并且显示了广泛的范围。该反应也适用于低聚硅氧烷的官能化。
• Catching Elusive 2-Furyl Carbenes with Silanes: A Metal-Free Microwave-Assisted Silicon-Hydrogen Bond Functionalization
  作者：Silvia González-Pelayo、Luis A. López

  DOI：10.1002/adsc.201601037

  日期：2016.12.22

  An efficient, metal‐free, silicon–hydrogen bond functionalization based on the microwave‐assisted reaction of readily available enynones and silanes is reported. This process seemingly proceeds through a 2‐furyl carbene species, a particularly elusive intermediate. Preliminary studies on the metal‐free oxygen–hydrogen and nitrogen–hydrogen bond functionalization of representative alcohols, azoles and

  据报道，基于微波的易得的烯酮和硅烷反应可实现高效，无金属的硅氢键官能化。这个过程似乎是通过2-呋喃基卡宾物质（特别难以捉摸的中间体）进行的。还提供了对代表性醇，唑和磺酰胺的无金属氧氢键和氮氢键功能的初步研究。
• Rhodium-Catalyzed Si–H Bond Insertion Reactions Using Functionalized Alkynes as Carbene Precursors
  作者：Ming-Yao Huang、Ji-Min Yang、Yu-Tao Zhao、Shou-Fei Zhu

  DOI：10.1021/acscatal.9b01187

  日期：2019.6.7

  method for preparing chiral organosilicons; however, all the carbene precursors used to date in this reaction have been diazo compounds, which significantly limits the structural diversity of the resulting chiral organosilicons. Herein, we report a protocol for rhodium-catalyzed asymmetric Si–H bond insertion reactions that use functionalized alkynes as carbene precursors. With chiral dirhodium tetracarboxylates

  对映选择性过渡金属催化的卡宾插入Si-H键是一种制备手性有机硅的有前途的方法。然而，迄今为止，该反应中使用的所有卡宾前体都是重氮化合物，这大大限制了所得手性有机硅的结构多样性。在本文中，我们报告了使用功能化炔烃作为卡宾前体的铑催化的不对称Si–H键插入反应的方案。用手性四羧酸二氢吡啶鎓作为催化剂，羰基烯炔和硅烷的反应可平稳地以高收率（高达98％）和出色的对映选择性（高达98％ee）得到手性有机硅烷。动力学研究表明，将原位生成的羰基铑插入硅烷的Si-H键中可能是决定速率的步骤。