[1-(furan-2-yl)ethoxy](triethyl)silane | 18032-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: [1-(furan-2-yl)ethoxy](triethyl)silane
• 英文别名: [1-(furanyl-2-yl)ethoxy]triethylsilane；triethyl(1-(furan-2-yl)ethoxy)silane；triethyl-(1-furan-2-yl-ethoxy)-silane；<1-Furyl-(2)-aethoxy>-triaethyl-silan；Triethyl-[1-(furan-2-yl)ethoxy]silane
• CAS: 18032-22-9
• 化学式: C₁₂H₂₂O₂Si
• 分子量: 226.391
• InChiKey: OPRWOUCTGSGVAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1-(furan-2-yl)ethoxy](triethyl)silane 在 bis(diisopropylamino)cyclopropenium chloride 、 potassium fluoride 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以91%的产率得到苯甲醇
  参考文献：
  名称：

  Phase-Transfer Catalyzed O-Silyl Ether Deprotection Mediated by a Cyclopropenium Cation

  摘要：

  The use of a cyclopropenium cation as a phase transfer catalyst for O-silyl ether deprotection is reported. Mechanistic insight into this deprotection methodology derived by linear free-energy relationships (LFER), quantum theory of atoms in molecules (QTAIM), and density functional theory (DFT) calculations are also provided.

  DOI：

  10.1021/acs.joc.6b02733
• 作为产物：
  描述：

  DL-1-(2-呋喃基)乙醇 、 三乙基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以92%的产率得到[1-(furan-2-yl)ethoxy](triethyl)silane
  参考文献：
  名称：

  Phase-Transfer Catalyzed O-Silyl Ether Deprotection Mediated by a Cyclopropenium Cation

  摘要：

  The use of a cyclopropenium cation as a phase transfer catalyst for O-silyl ether deprotection is reported. Mechanistic insight into this deprotection methodology derived by linear free-energy relationships (LFER), quantum theory of atoms in molecules (QTAIM), and density functional theory (DFT) calculations are also provided.

  DOI：

  10.1021/acs.joc.6b02733

文献信息

• A mild and efficient method for the selective deprotection of silyl ethers using KF in the presence of tetraethylene glycol
  作者：Hailong Yan、Joong-Suk Oh、Choong Eui Song

  DOI：10.1039/c1ob06300f

  日期：——

  efficient protocol for the deprotection of silyl ethers using KF in tetraethylene glycol is reported. A wide range of alcoholic silyl ethers can be selectively cleaved in high yield in the presence of certain acid- and base-labile functional groups. Moreover, the phenolic silyl ethers were cleaved exclusively, without affecting the alcoholic silyl ethers, at room temperature.

  一个温和而有效的协议，用于使用以下方法脱甲硅烷基醚 肯尼迪 在 四甘醇被报道。在某些对酸和碱不稳定的官能团的存在下，可以高产率选择性地裂解多种醇式甲硅烷基醚。此外，在室温下仅裂解酚类甲硅烷基醚，而不会影响醇类甲硅烷基醚。
• Iridacycles as Catalysts for the Autotandem Conversion of Nitriles into Amines by Hydrosilylation: Experimental Investigation and Scope
  作者：Mustapha Hamdaoui、Camille Desrousseaux、Houda Habbita、Jean-Pierre Djukic

  DOI：10.1021/acs.organomet.7b00749

  日期：2017.12.26

  heterolytic activation of the Si–H bond. The molecular structure of a new example of such an adduct was resolved by X-ray diffraction analysis. Theoretical considerations support a donor–acceptor [C,N}Cp*IrIII-H]→[SiEt3]+ (C,N} = benzo[h]quinolinyl) formulation where the cationic silyl moiety acting as a Z ligand binds both Ir and H centers. Under the conditions of the catalysis, the latter adduct is assumed

  合成了含有（五甲基环戊二烯基）铱（III）单元的一组iridacycles [C，N} Cp * Ir III -Cl]（C，N} =苯并[ h ]喹啉，二苯并[ f，h ]喹啉）并衍生为与BArF型阴离子缔合的阳离子[C，N} Cp * Ir-NCMe] +。后者的盐因其在H 2中对HSiEt 3的潜在催化性能而进行了基准测试-释放测试反应。表现最佳的BArF型盐显示出能够以低的催化负载量（大约）促进反应的能力。乙腈，丙腈和一系列芳腈底物的自动串联氢化硅烷化为0.5–1 mol％。机理研究证实，Si-H键的亲电和杂合活化可初步形成硅烷-铱环加合物。通过X射线衍射分析解析了这种加合物的新实例的分子结构。理论上的考虑支持了施主-受主[C，N} Cp * Ir III -H]→[SiEt 3 ] +（C，N} =苯并[ h ]喹啉基）的配方，其中阳离子甲硅烷基部分充当Z配体结合Ir和
• Electrochemical flow-reactor for expedient synthesis of copper–N-heterocyclic carbene complexes
  作者：Michael R. Chapman、Yarseen M. Shafi、Nikil Kapur、Bao N. Nguyen、Charlotte E. Willans

  DOI：10.1039/c4cc08874c

  日期：——

  An electrochemical flow-cell has been developed for the highly efficient and selective generation of organometallic Cu^I–N-heterocyclic carbene complexes under neutral and ambient conditions.

  已经开发出一种电化学流动电池，用于在中性和环境条件下高效选择性地生成有机金属Cu^I–N-杂环卡宾配合物。
• A Simple and Efficient Copper-Catalyzed Procedure for the Hydrosilylation of Hindered and Functionalized Ketones
  作者：Silvia Díez-González、Harneet Kaur、Fabiano Kauer Zinn、Edwin D. Stevens、Steven P. Nolan

  DOI：10.1021/jo050397v

  日期：2005.6.1

  The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC-HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.