(tris-(4-fluorophenyl))chlorosilane | 850-61-3

• 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: (tris-(4-fluorophenyl))chlorosilane
• 英文别名: chlorotris(4-fluorophenyl)silane；Tris-(p-fluorphenyl)-chlor-silan；Tris(p-fluorophenyl)chlorosilane；chloro-tris(4-fluorophenyl)silane
• CAS: 850-61-3
• 化学式: C₁₈H₁₂ClF₃Si
• 分子量: 348.827
• InChiKey: NTJWPAFELHFJFE-UHFFFAOYSA-N

物化性质

• 熔点：
  81 °C
• 沸点：
  366.8±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (tris-(4-fluorophenyl))chlorosilane 在 四丁基高氯酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以2.3%的产率得到hexakis(p-fluorophenyl)disilane
  参考文献：
  名称：

  An electrochemical method for the synthesis of silicon—silicon bonds

  摘要：

  DOI：

  10.1016/s0022-328x(00)81911-7
• 作为产物：
  描述：

  对溴氟苯 在 四氯化硅 、 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (tris-(4-fluorophenyl))chlorosilane
  参考文献：
  名称：

  Preparation, characterization and properties of dipolar 1,2-N,N-dimethylaminomethylferrocenylsilanes

  摘要：

  A series of substituted 1,2-N,N-dimethylaminomethylferrocenyl compounds were synthesized and characterized by H-1-NMR, C-13-NMR, Si-29-NMR, ES-MS, IR, UV-vis and Fe-57-Mossbauer spectroscopy. The new (R,S)-2-(N,N-dimethylaminomethyl)ferrocenyl-(aryl)silanes (R,S)-FcNSiMe(n) (C6H4X)(m) (n = 2-0, m = 1, X = p-F (5); m = 2, X = p-F (6); m = 3, X = p-F (7) and m = 1, X = p-Br (14) were formed by the reaction of 2-dimethylaminomethylferrocenyllithium FcNLi (1) with chloroarylsilanes Clsi(Me)(n) (C6H4X)(m) (n = 2-0, m = 1, X = p-F (2); m = 2, X = p-F (3); m = 3, X = p-F (4) and m = 1, X = p-Br (13)). The treatment of 5, 6 and 14 with gaseous hydrogen chloride or picric acid resulted in the formation of the hydrochloride complexes 9, 10, 15 and the picrates 11, 12 and 16. The treatment of 14 with LiR or Mg and DMF resulted in the formation of (R,S)-2-(N,N-dimethylaminomethyl)ferrocenyl(4-formylphenyl)dimethylsilane (18). The crystal structures of 7, 12 and 15 were determined by single crystal X-ray analyses. Fe-57-Mossbauer spectroscopy gives evidence of a significant electronic coupling between the ferrocenyl unit and the organic acceptor moiety of the molecules in the ground state. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01427-4

文献信息

• Linear Free-Energy Relationship and Rate Study on a Silylation-Based Kinetic Resolution: Mechanistic Insights
  作者：Ravish K. Akhani、Maggie I. Moore、Julia G. Pribyl、Sheryl L. Wiskur

  DOI：10.1021/jo402569h

  日期：2014.3.21

  factors to Charton values was also observed when just alkyl substituents were employed but was nonexistent when substituents with more electronic effects were incorporated. The rate data suggest that a significant redistribution of charge occurs in the transition state, with an overall decrease in positive charge. The linear free-energy relationship derived from selectivity factors is best understood by

  探索了不同的对位取代的三苯基甲硅烷基氯的取代基对基于甲硅烷基化的动力学拆分的影响。给电子基团减慢反应速率并提高选择性，而吸电子基团增加反应速率并降低选择性。发现线性自由能关系都选择性因素和初始利率为σ相关对哈米特参数。当仅使用烷基取代基时，还观察到选择性因子与Charton值之间的相关性较弱，但是当引入具有更多电子效应的取代基时，则不存在选择性因子与Charton值的弱相关性。速率数据表明，在过渡状态下会发生明显的电荷重新分布，而正电荷会总体上减少。Hammond假设可以最好地理解源自选择性因子的线性自由能关系。早期和晚期过渡态描述了底物在过渡态中的参与量，因此描述了两种对映异构体的非对映体过渡态之间的能量差。这项工作突出了我们在基于甲硅烷基化的动力学拆分中努力理解选择性的机理和起源的努力。
• YAMAMURO, CATOPY
  作者：YAMAMURO, CATOPY

  DOI：——

  日期：——
• An electrochemical method for the synthesis of silicon—silicon bonds
  作者：E. Hengge、H. Firgoi

  DOI：10.1016/s0022-328x(00)81911-7

  日期：1981.6
• Preparation, characterization and properties of dipolar 1,2-N,N-dimethylaminomethylferrocenylsilanes
  作者：Christian Beyer、Uwe Böhme、Claus Pietzsch、Gerhard Roewer

  DOI：10.1016/s0022-328x(02)01427-4

  日期：2002.7

  A series of substituted 1,2-N,N-dimethylaminomethylferrocenyl compounds were synthesized and characterized by H-1-NMR, C-13-NMR, Si-29-NMR, ES-MS, IR, UV-vis and Fe-57-Mossbauer spectroscopy. The new (R,S)-2-(N,N-dimethylaminomethyl)ferrocenyl-(aryl)silanes (R,S)-FcNSiMe(n) (C6H4X)(m) (n = 2-0, m = 1, X = p-F (5); m = 2, X = p-F (6); m = 3, X = p-F (7) and m = 1, X = p-Br (14) were formed by the reaction of 2-dimethylaminomethylferrocenyllithium FcNLi (1) with chloroarylsilanes Clsi(Me)(n) (C6H4X)(m) (n = 2-0, m = 1, X = p-F (2); m = 2, X = p-F (3); m = 3, X = p-F (4) and m = 1, X = p-Br (13)). The treatment of 5, 6 and 14 with gaseous hydrogen chloride or picric acid resulted in the formation of the hydrochloride complexes 9, 10, 15 and the picrates 11, 12 and 16. The treatment of 14 with LiR or Mg and DMF resulted in the formation of (R,S)-2-(N,N-dimethylaminomethyl)ferrocenyl(4-formylphenyl)dimethylsilane (18). The crystal structures of 7, 12 and 15 were determined by single crystal X-ray analyses. Fe-57-Mossbauer spectroscopy gives evidence of a significant electronic coupling between the ferrocenyl unit and the organic acceptor moiety of the molecules in the ground state. (C) 2002 Elsevier Science B.V. All rights reserved.