1-tris(pentafluorophenyl)silyloxycyclopentene | 705933-33-1

• 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: 1-tris(pentafluorophenyl)silyloxycyclopentene
• 英文别名: cyclopenten-1-yloxy-tris(2,3,4,5,6-pentafluorophenyl)silane
• CAS: 705933-33-1
• 化学式: C₂₃H₇F₁₅OSi
• 分子量: 612.37
• InChiKey: JJRADMCAQVSRQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [4-[(4-methoxyphenyl)methylidene]cyclohexa-2,5-dien-1-ylidene]-methyloxidanium;chloride 、 1-tris(pentafluorophenyl)silyloxycyclopentene 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以67%的产率得到2-[bis(4-methoxyphenyl)methyl]cyclopentanone
  参考文献：
  名称：

  含有 (C6F5)3SiO 和 (C6H5)3SiO 基团的甲硅烷基乙烯酮缩醛和甲硅烷基烯醇醚的亲核反应性

  摘要：

  三（五氟苯基）甲硅烷基和三苯基甲硅烷基乙烯酮缩醛和烯醇醚与二苯甲基阳离子的反应动力学已通过光度计测量。二阶速率常数 (log k2) 已用于确定这些 π 系统的亲核性参数，这提供了它们与其他类型亲核试剂反应性的定量比较。从三甲基甲硅烷氧基变为三苯基甲硅烷氧基只会将反应性降低十倍，而用三（五氟苯基）甲硅烷氧基取代三苯基甲硅烷氧基会使烯醇化 C=C 双键的亲核性降低三到四个数量级。因此，三(五氟苯基)甲硅烷氧基的阳离子稳定能力类似于甲基的阳离子稳定能力。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany,

  DOI：

  10.1002/ejoc.200400706
• 作为产物：
  描述：

  氯三(2,3,4,5,6-五氟苯基)硅烷 、 环戊酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以72%的产率得到1-tris(pentafluorophenyl)silyloxycyclopentene
  参考文献：
  名称：

  Tris(pentafluorophenyl)silyl enol ethers: synthesis and aldol reactions

  摘要：

  Silyl enol ethers bearing three pentafluorophenyl groups at the silicon atom are described. These Compounds undergo uncatalyzed aldol reactions with aliphatic, alpha,beta-unsaturated, and aromatic aldehydes. The observed reactivity is analyzed in terms of the Lewis acidity of the silyl fragment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.090

文献信息

• Complexation of tris(pentafluorophenyl)silanes with neutral Lewis bases
  作者：Alexander D. Dilman、Vitalij V. Levin、Alexander A. Korlyukov、Pavel A. Belyakov、Marina I. Struchkova、Mikhail Yu. Antipin、Vladimir A. Tartakovsky

  DOI：10.1016/j.jorganchem.2007.12.022

  日期：2008.3

  A detailed analysis of monodentate and bidentate complexation of tris(pentafluorophenyl) silyl (TPFS) derivatives with neutral Lewis bases was performed. The NMR spectroscopy and X-ray diffraction analysis (11 structures) were the key methods to characterize tetraor pentacoordinate silicon compounds, whereas the peculiarities of crystal packing were analyzed by means of DFT calculations. The interaction of TPFS-X (X = F, Cl, OTf) with strong Lewis bases (HMPA, N-methylpyrrolidinone) may afford three different species: neutral pentacoordinate TPFS(X)-L, cationic tetracoordinate TPFS-L+ X-, and cationic pentacoordinate TPFS-(L)(2)X-+(-), representatives of each type were characterized by X-ray diffraction. A variety of complexes with bidentate complexation, featuring the trigonal bipyramidal geometry with apical C6F5-group was prepared and structurally characterized. The extent of Si-C-apical bond elongation depends on the donating ability of the coordinating ligand, with the longest Si-C bond of 1.981(1) angstrom observed for six-membered complex of TPFS-ether of N-(2-hydroxybenzoyl) pyrrolidine. (C) 2007 Elsevier B.V. All rights reserved.
• Tris(pentafluorophenyl)silyl enol ethers: synthesis and aldol reactions
  作者：Alexander D Dilman、Pavel A Belyakov、Alexander A Korlyukov、Vladimir A Tartakovsky

  DOI：10.1016/j.tetlet.2004.03.090

  日期：2004.5

  Silyl enol ethers bearing three pentafluorophenyl groups at the silicon atom are described. These Compounds undergo uncatalyzed aldol reactions with aliphatic, alpha,beta-unsaturated, and aromatic aldehydes. The observed reactivity is analyzed in terms of the Lewis acidity of the silyl fragment. (C) 2004 Elsevier Ltd. All rights reserved.
• Nucleophilic Reactivities of Silyl Ketene Acetals and Silyl Enol Ethers Containing (C6F5)3SiO and (C6H5)3SiO Groups
  作者：Alexander D. Dilman、Herbert Mayr

  DOI：10.1002/ejoc.200400706

  日期：2005.5

  kinetics of the reactions of tris(pentafluorophenyl)silyl and triphenylsilyl ketene acetals and enol ethers with benzhydrylium cations have been measured photometrically. The second-order rate constants (log k2) have been used to determine the nucleophilicity parameters of these π systems, which provide a quantitative comparison of their reactivities with those of other types of nucleophiles. A change

  三（五氟苯基）甲硅烷基和三苯基甲硅烷基乙烯酮缩醛和烯醇醚与二苯甲基阳离子的反应动力学已通过光度计测量。二阶速率常数 (log k2) 已用于确定这些 π 系统的亲核性参数，这提供了它们与其他类型亲核试剂反应性的定量比较。从三甲基甲硅烷氧基变为三苯基甲硅烷氧基只会将反应性降低十倍，而用三（五氟苯基）甲硅烷氧基取代三苯基甲硅烷氧基会使烯醇化 C=C 双键的亲核性降低三到四个数量级。因此，三(五氟苯基)甲硅烷氧基的阳离子稳定能力类似于甲基的阳离子稳定能力。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany,