1-bromo-1-trimethylsilyl-3-phenylpropane

• 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-bromo-1-trimethylsilyl-3-phenylpropane
• 英文别名: 1-bromo-3-phenyl-1-trimethylsilylpropane；(1-bromo-3-phenylpropyl)trimethylsilane；(1-Bromo-3-phenylpropyl)-trimethylsilane
• 化学式: C₁₂H₁₉BrSi
• 分子量: 271.272
• InChiKey: OAZFGUJQQRRODG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-bromo-1-trimethylsilyl-3-phenylpropane 、 (2-(1,3-dioxolan-2-yl)ethyl)zinc(II) bromide 在 NiBr2*diglyme 、 2,6-二[(4S)-4-叔丁基-2-恶唑啉基]吡啶 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 以86%的产率得到
  参考文献：
  名称：

  烷基亲电子试剂的对映会聚交叉偶联：有机硅烷的催化不对称合成。

  摘要：

  金属催化的烷基亲电子试剂的对映会聚交叉偶联反应正在成为不对称合成中的有力工具。迄今为止，高对映选择性仅限于带有导向基团或近端 p/π 轨道的亲电子试剂的偶联。在此，我们首次证明对映异构交叉偶联可以通过缺乏此类特征的亲电子试剂来实现；具体来说，我们确定手性镍催化剂可以在简单温和的条件下完成外消旋α-卤代硅烷与烷基锌试剂的根岸反应，具有良好的对映选择性，从而提供对映体富集的有机硅烷（一类重要的目标分子）的途径。

  DOI：

  10.1002/anie.201814208
• 作为产物：
  描述：

  溴甲苯 、 乙烯基三甲基硅烷 在 五羰基铁 、 N,N-二甲基甲酰胺 作用下， 反应 2.0h， 以38.3%的产率得到1-bromo-1-trimethylsilyl-3-phenylpropane
  参考文献：
  名称：

  Homolytic addition of benzyl bromide to unsaturated compounds in conditions of metal-complex initiation

  摘要：

  Radical addition of benzyl bromide to unsaturated compounds containing substituents of a different polar nature, CH2=CHX (X = C4H9, SiMe3, CF3, CO2Me, CN, H), was conducted in the presence of the Fe (CO)5 + DMF (HMPA) system. Adducts were obtained and their structure was demonstrated by C-13 NMR and mass spectrometry.

  DOI：

  10.1007/bf00863820

文献信息

• Radical-type addition of benzyl bromide to vinyl chloride: the kinetics and activation energy of the process
  作者：T. T. Vasil'eva、S. I. Gapusenko、A. B. Terent'ev、V. V. Pinyaskin、I. V. Stankevich、A. L. Chistyakov、E. I. Mysov

  DOI：10.1007/bf00698942

  日期：1993.5

  Radical telomerization of vinyl chloride with benzyl bromide and the competitive reaction of benzyl bromide with vinyl chloride and trimethylvinylsilane have been studied. The relative rate constant for the addition of C6H5C · H2 to vinyl chloride,krel (with respect to trimethylvinylsilane), is close to unity, whereas the activation energy of the addition of C6H5C.H2 to vinyl chloride is considerably

  研究了氯乙烯与苄基溴的自由基调聚反应以及苄基溴与氯乙烯和三甲基乙烯基硅烷的竞争反应。C6H5C·H2 添加到氯乙烯 krel 的相对速率常数（相对于三甲基乙烯基硅烷）接近 1，而 C6H5C·H2 添加到氯乙烯的活化能要低得多（7 kcal mol -1) 比在涉及三甲基乙烯基硅烷的反应中。自由基加成物 C6H5CH2CH2C.HCl 的可能碎裂被认为是低估 krel 的可能原因之一。活化能通过 MPDO/3 方法估算。
• Study of the mechanism of the addition of benzyl bromide to trimethylvinylsilane in the presence of the Fe(CO)5?DMF system
  作者：A. B. Terent'ev、S. I. Gapusenko、T. T. Vasil'eva

  DOI：10.1007/bf00699930

  日期：1993.8

  The general kinetics of the addition of benzyl bromide to trimethylvinylsilane in the presence of the Fe(CO)5—DMF system has been studied. The reaction orders with respect to each reagent found in the study correspond to a radical chain mechanism of the process. The metal-complex system takes part only in the initiation stage and only at a strictly defined ratio of the components.

  研究了在 Fe(CO)5-DMF 体系存在下，苄基溴加成到三甲基乙烯基硅烷的一般动力学。研究中发现的每种试剂的反应顺序对应于该过程的自由基链机制。金属络合物系统仅在初始阶段参与，并且仅以严格定义的组分比例参与。
• Balabanova, L. V.; Terent'ev, A. B.; Vasil'eva, T. T., Russian Journal of General Chemistry, 1993, vol. 63, # 10.1, p. 1574 - 1575
  作者：Balabanova, L. V.、Terent'ev, A. B.、Vasil'eva, T. T.、Gapusenko, S. I.、Churkina, T. D.

  DOI：——

  日期：——
• Terent'ev, A. B.; Gapusenko, S. I.; Vasil'eva, T. T., Russian Journal of Organic Chemistry, <hi>1992</hi>, vol. 28, # 8.1, p. 1257 - 1259
  作者：Terent'ev, A. B.、Gapusenko, S. I.、Vasil'eva, T. T.、Dostovalova, V. I.

  DOI：——

  日期：——
• Homolytic addition of benzyl bromide to unsaturated compounds in conditions of metal-complex initiation
  作者：T. T. Vasil'eva、S. I. Gapusenko、S. V. Vitt、A. B. Terent'ev

  DOI：10.1007/bf00863820

  日期：1992.10

  Radical addition of benzyl bromide to unsaturated compounds containing substituents of a different polar nature, CH2=CHX (X = C4H9, SiMe3, CF3, CO2Me, CN, H), was conducted in the presence of the Fe (CO)5 + DMF (HMPA) system. Adducts were obtained and their structure was demonstrated by C-13 NMR and mass spectrometry.

表征谱图