(4-ferrocenylbutyl)dimethylsilane | 102744-79-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 芳香烃
• 英文名称: (4-ferrocenylbutyl)dimethylsilane
• 英文别名: cyclopenta-1,3-diene;4-cyclopenta-2,4-dien-1-ylbutyl(dimethyl)silane;iron(2+)
• CAS: 102744-79-6
• 化学式: C₁₆H₂₄FeSi
• 分子量: 300.299
• InChiKey: RSQDHEQHGBTGHO-UHFFFAOYSA-N

物化性质

• 沸点：
  130-140℃ at 1hPa

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  (4-ferrocenylbutyl)dimethylsilane 、 1,1'-bis(3-butenyl)-3-butylferrocene 在 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以57%的产率得到
  参考文献：
  名称：

  Synthesis, characterization and electrochemical properties of novel trinuclear ferrocenyl based organosilane compounds

  摘要：

  Some trinuclear ferrocenyl based organosilane compounds were synthesized by hydrosilylation reaction of [4-(ethylferrocenyl)butyl]dimethylsilane and (4-ferrocenylbutyl)dimethylsilane with bisalkenylferrocene derivatives, in the presence of the Karstedt catalyst at room temperature. In addition a simple method for the preparation of 1,1'-bis(3-butenyl)alkylferrocenes from 1,1'-bis(4-chlorobutyl)alkylferrocenes under mild conditions was developed. H-1 and C-13 NMR, FT-IR, GC MS, CHN analysis, atomic absorbtion spectroscopy supported the predicted structure of the products. The electrochemical behavior of synthesized compounds was studied by cyclic voltammetry in CH3CN/0.1 M LiClO4 utilizing a glasse carbon working electrode. The relationship between the peak currents and the square root of the scan rate, showed that the redox process is diffusion limited. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.02.001
• 作为产物：
  描述：

  二甲基一氯硅烷 、 4-chlorobutylferrocene 在 magnesium 作用下， 生成 (4-ferrocenylbutyl)dimethylsilane
  参考文献：
  名称：

  Synthesis of novel ferrocenyl silyl ethers via dehydrocoupling reactions under Karstedt catalyst

  摘要：

  (4-ferrocenylbutyl)dimethylsilane 可通过 Grignard 反应由 4-chlorobutylferrocene 和 chlorodimethylsilane 在 THF 中制备。Si-H 键在室温下与伯醇和仲醇反应，在 THF 中使用 Karstedt 催化剂，可获得高产率的 (4-ferrocenylbutyl)dimethylsilyl 醚。含 hanging side chain 中的 ferrocenyl 基团可通过室温下使用 Karstedt 催化剂进行的醇解反应附着于 cellulose acetate butyrate。© 2013 Elsevier B.V. 保留所有权利。

  DOI：

  10.1016/j.jorganchem.2013.04.027

文献信息

• Synthesis of new binuclear ferrocenyl compounds by hydrosilylation reactions
  作者：Reza Teimuri-Mofrad、Farzaneh Mirzaei、Hassan Abbasi、Kazem D. Safa

  DOI：10.1016/j.crci.2016.06.011

  日期：2017.2

  Résumé Ferrocenyl silanes are prepared by treatment of Grignard reagents produced from 4-chlorobutylferrocene derivatives and chlorodimethylsilane in THF. Butenylferrocenes are prepared by the elimination reaction of 4-chlorobutylalkylferrocenes by sodium tert-butoxide in DMSO. A hydrosilylation reaction between a butenyl compound and ferrocenylsilane occurred in dry toluene at room temperature in the presence of the Karstedt catalyst to produce the desired binuclear ferrocenyl compound in good to high yields. The electrochemical behavior of new ferrocenyl compounds were studied by cyclic voltammetry in CH3CN/0.1 M LiClO4, and the relation between the peak currents and the square root of the scan rate, showed that the redox process is diffusion-limited.

  简历 Ferrocenylsilane类化合物通过在THF中处理由4-氯丁基二茂铁衍生物和氯二甲基硅烷制备的Grignard试剂来合成。丁烯基二茂铁化合物通过在DMSO中使用叔丁醇钠对4-氯丁基烷基二茂铁进行消除反应来制备。在Karstedt催化剂存在下，在室温下干燥甲苯中，丁烯基化合物与二茂铁基硅烷之间的氢硅烷化反应发生，以良好的至高产率产生所需的二核二茂铁基化合物。新二茂铁基化合物的电化学行为通过在CH3CN/0.1 M LiClO4中进行循环伏安法进行了研究，峰值电流与扫描速率的平方根之间的关系表明氧化还原过程受扩散限制。
• [EN] PROCESS FOR THE SYNTHESIS OF SILYLFERROCENE COMPOUNDS<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE COMPOSÉS SILYLFERROCÈNES
  申请人：CBZ CHEMICALS LTD

  公开号：WO2011048615A1

  公开（公告）日：2011-04-28

  The invention provides for a process for the preparation of a silylferrocene compound, comprising the steps of treating ferrocene with a 4-chloroalkyryl chloride in the presence of an lewis acid catalyst and an organic solvent to obtain the acylated product, reducing the acylated product to obtain the 4- chloralkylferrocene, treating the 4-chloroalkylferroce with a metal under Grignard reaction conditions to form its corresponding Grignard intermediate compound; and reacting with chloroalkylsilane in-situ to give the silylferrocene compound. The silylferrocene compound 4-(dimethylsilyl)butylferrocene can be prepared by the process of the invention.

  该发明提供了一种制备硅基二茂铁化合物的方法，包括以下步骤：在Lewis酸催化剂和有机溶剂的存在下，用4-氯烷基氯化物处理二茂铁以获得酰化产物，将酰化产物还原以获得4-氯烷基二茂铁烯，将4-氯烷基二茂铁烯在格氏试剂反应条件下与金属反应以形成其相应的格氏试剂中间体化合物；并在原位与氯烷基硅烷反应以给出硅基二茂铁化合物。通过该方法可以制备硅基二茂铁化合物4-(二甲基硅基)丁基二茂铁烯。
• PROCESS FOR THE SYNTHESIS OF 4-(DIMETHYLSILYL) BUTYLFERROCENE
  申请人：Pradhan Braja Sundar

  公开号：US20120209019A1

  公开（公告）日：2012-08-16

  The invention provides for a process for the preparation of a silylferrocene compound, comprising the steps of treating ferrocene with a 4-chloroalkyryl chloride in the presence of an lewis acid catalyst and an organic solvent to obtain the acylated product, reducing the acylated product to obtain the 4-chloralkylferrocene, treating the 4-chloroalkylferroce with a metal under Grignard reaction conditions to form its corresponding Grignard intermediate compound; and reacting with chloroalkylsilane in-situ to give the silylferrocene compound. The silylferrocene compound 4-(dimethylsilyl)butylferrocene can be prepared by the process of the invention.

  该发明提供了一种用于制备硅基二茂铁化合物的方法，包括以下步骤：在Lewis酸催化剂和有机溶剂的存在下，用4-氯烷基氯化物处理二茂铁以获得酰化产物，还原酰化产物以获得4-氯烷基二茂铁，用金属在格氏试剂反应条件下处理4-氯烷基二茂铁以形成相应的格氏试剂中间体化合物；并与氯烷基硅烷原位反应以得到硅基二茂铁化合物。通过该发明的方法可以制备硅基二茂铁化合物4-(二甲基硅基)丁基二茂铁。
• Process for the synthesis of 4-(dimethylsilyl) butylferrocene
  申请人：Pradhan Braja Sundar

  公开号：US08664417B2

  公开（公告）日：2014-03-04

  The invention provides for a process for the preparation of a silylferrocene compound, comprising the steps of treating ferrocene with a 4-chloroalkyryl chloride in the presence of an lewis acid catalyst and an organic solvent to obtain the acylated product, reducing the acylated product to obtain the 4-chloralkylferrocene, treating the 4-chloroalkylferroce with a metal under Grignard reaction conditions to form its corresponding Grignard intermediate compound; and reacting with chloroalkylsilane in-situ to give the silylferrocene compound. The silylferrocene compound 4-(dimethylsilyl)butylferrocene can be prepared by the process of the invention.

  本发明提供了一种制备硅基二茂铁化合物的方法，包括以下步骤：在路易斯酸催化剂和有机溶剂存在下，用4-氯烷基氯化物处理二茂铁以获得酰化产物，还原酰化产物以得到4-氯烷基二茂铁，将4-氯烷基二茂铁在Grignard反应条件下与金属反应，形成其相应的Grignard中间体化合物；并现场用氯烷基硅烷反应得到硅基二茂铁化合物。通过本发明的方法可以制备硅基二茂铁化合物4-（二甲基硅基）丁基二茂铁。
• Synthesis, characterization and electrochemical properties of novel trinuclear ferrocenyl based organosilane compounds
  作者：Reza Teimuri-Mofrad、Kazem D. Safa、Keshvar Rahimpour

  DOI：10.1016/j.jorganchem.2014.02.001

  日期：2014.5

  Some trinuclear ferrocenyl based organosilane compounds were synthesized by hydrosilylation reaction of [4-(ethylferrocenyl)butyl]dimethylsilane and (4-ferrocenylbutyl)dimethylsilane with bisalkenylferrocene derivatives, in the presence of the Karstedt catalyst at room temperature. In addition a simple method for the preparation of 1,1'-bis(3-butenyl)alkylferrocenes from 1,1'-bis(4-chlorobutyl)alkylferrocenes under mild conditions was developed. H-1 and C-13 NMR, FT-IR, GC MS, CHN analysis, atomic absorbtion spectroscopy supported the predicted structure of the products. The electrochemical behavior of synthesized compounds was studied by cyclic voltammetry in CH3CN/0.1 M LiClO4 utilizing a glasse carbon working electrode. The relationship between the peak currents and the square root of the scan rate, showed that the redox process is diffusion limited. (C) 2014 Elsevier B.V. All rights reserved.