(4-bromophenyl)triallylsilane | 450371-47-8

• 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: (4-bromophenyl)triallylsilane
• 英文别名: Silane, (4-bromophenyl)tri-2-propenyl-；(4-bromophenyl)-tris(prop-2-enyl)silane
• CAS: 450371-47-8
• 化学式: C₁₅H₁₉BrSi
• 分子量: 307.305
• InChiKey: LQHLVCZFLLBWDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (4-bromophenyl)triallylsilane 在 正丁基锂 、 硼酸三异丙酯 、 盐酸 作用下， 以 乙醚 、 正己烷 为溶剂， 以67%的产率得到4-(triallylsilyl)phenylboronic acid
  参考文献：
  名称：

  一种高效的会聚合成新型各向异性吸附剂的方法，该方法基于端基为三烯丙基甲硅烷基的纳米级和三脚形的低聚亚苯基。

  摘要：

  本文介绍了一种新型的三脚架形状的低聚亚苯基化合物的有效和收敛的合成。该化合物由三个四面体硅原子上的三脚撑低聚亚苯基七聚体和三官能团一个溴苯基组成。每个三脚架腿都用三烯丙基甲硅烷基封端，以通过氢化硅烷化将分子共价锚定在氢封端的硅表面上。该化合物可以代表一种新型的各向异性吸附物，用于控制有机薄膜中官能团的取向和间距以及在硅表面上生长的纳米结构的间距。端基为三烯丙基甲硅烷基和频哪醇芳基硼酸酯基的低聚亚苯基六聚物很容易通过选择性的Suzuki偶联反应从二碘三苯基与溴苯基硼酸衍生而来。为在竞争性的Heck反应中存在多个乙烯基，开发了位阻频哪醇硼酸酯与芳基碘的高度选择性Suzuki偶联的反应条件。在最佳条件下（Pd（PPh3）4 / KOH / Bu4NBr /甲苯/ H2O，85摄氏度，过夜），对溴苯基-三（对碘苯基）硅烷与3个当量的六亚苯基硼酸酯反应生成由22个亚苯基和9个烯丙基组成的三脚架形低聚亚苯基，收率为78％。

  DOI：

  10.1021/jo0257750
• 作为产物：
  描述：

  对溴苯基三氯硅烷 、 烯丙基溴化镁 以 乙醚 为溶剂， 以79%的产率得到(4-bromophenyl)triallylsilane
  参考文献：
  名称：

  一种高效的会聚合成新型各向异性吸附剂的方法，该方法基于端基为三烯丙基甲硅烷基的纳米级和三脚形的低聚亚苯基。

  摘要：

  本文介绍了一种新型的三脚架形状的低聚亚苯基化合物的有效和收敛的合成。该化合物由三个四面体硅原子上的三脚撑低聚亚苯基七聚体和三官能团一个溴苯基组成。每个三脚架腿都用三烯丙基甲硅烷基封端，以通过氢化硅烷化将分子共价锚定在氢封端的硅表面上。该化合物可以代表一种新型的各向异性吸附物，用于控制有机薄膜中官能团的取向和间距以及在硅表面上生长的纳米结构的间距。端基为三烯丙基甲硅烷基和频哪醇芳基硼酸酯基的低聚亚苯基六聚物很容易通过选择性的Suzuki偶联反应从二碘三苯基与溴苯基硼酸衍生而来。为在竞争性的Heck反应中存在多个乙烯基，开发了位阻频哪醇硼酸酯与芳基碘的高度选择性Suzuki偶联的反应条件。在最佳条件下（Pd（PPh3）4 / KOH / Bu4NBr /甲苯/ H2O，85摄氏度，过夜），对溴苯基-三（对碘苯基）硅烷与3个当量的六亚苯基硼酸酯反应生成由22个亚苯基和9个烯丙基组成的三脚架形低聚亚苯基，收率为78％。

  DOI：

  10.1021/jo0257750

文献信息

• Allyl‐End‐Grafted Carbosilane Dendrimers Based on 1,4‐Phenylene Units: Synthesis, Reactivity, Structure, and Bonding Motifs
  作者：Zakariyya Ishtaiwi、Tobias Rüffer、Alexander Hildebrandt、Firas F. Awwadi、Harald Hahn、Akerke Abylaikhan、Deeb Taher、Uwe Siegert、Bernhard Walfort、Heinrich Lang

  DOI：10.1002/ejic.201201428

  日期：2013.5

  Si[C6H4–4-SiMe2(CH2CH=CH2)]4 (7b) and ClSi[C6H4–4-SiC6H4–4-SiMe2(CH2CH=CH2)}3]3 (10a) in the solid state are reported. The crystal structures of both dendrimers are based on C–H···πCC (πCC = double bond of the CH=CH2 groups) and π–π interactions. The 3D network structure observed for 7b is composed of three crystallographically independent head-to-head stacking columns along the crystallographic b axis

  一系列 1-Br–C6H4–4-SiMe3–n(CH2CH=CH2)n (n = 1, 2, 3), Si[C6H4–4-SiMe3–n(CH2CH=CH2) 型碳硅烷的合成n]4, 1-Br–C6H4-4-Si[C6H4–4-SiMe3–n(CH2CH=CH2)n]3 (n = 0, 1, 2, 3), ClSi[C6H4–4-SiC6H4 –4-SiMe3–n(CH2CH=CH2)n}3]3, Si[C6H4–4-SiC6H4–4-SiMe3–n(CH2CH=CH2)n}3]4 (n = 1, 2),并讨论了 1-Br–C6H4–4-Si[C6H4–4-SiC6H4–4-SiMe3–n(CH2CH=CH2)n}3]3 (n = 0, 1, 2, 3)。Si[C6H4-4-SiMe2(CH2CH=CH2)]4(7b)和ClSi[C6H4-4-SiC6H4-4-SiMe2(CH2C
• (METH)ALLYLSILANE COMPOUND, SILANE COUPLING AGENT THEREOF, AND FUNCTIONAL MATERIAL USING THE SAME
  申请人：Shimada Toyoshi

  公开号：US20140200311A1

  公开（公告）日：2014-07-17

  A (meth)allylsilane compound that a functional group of a (meth)allylsilyl group or a halogenosilyl group bonded to the (meth)allylsilyl group via a spacer group is bonded directly or through a divergent spacer group to a dehydrogenated residue of an amino group of an amino group-containing compound; a carbaminic acid ester group or an amide group derived from a dehydrogenated residue of the amino group; an aromatic compound; a polymerizable unsaturated groups; perfluoro group; a dehydrogenated residue of saccharide or a carbohydrate polyol (excluding when the divergent spacer group is an alkylene group, or an alkylene group and an arylene group); a dehydrogenated residue of an amino acid; a halogenosilyl group; or a substituted silyl group in which a halogen of the halogenosilyl group is substituted.

  一种(meth)allylsilane化合物，其中一个(meth)allylsilyl基团或卤代silyl基团通过间隔基团直接或通过分散的间隔基团与含氨基化合物的氨基残基的脱氢残基；一个由氨基残基脱氢得到的氨基酸酯基团或酰胺基团；一个芳香化合物；一个可聚合的不饱和基团；全氟基团；糖或碳水化合物多元醇的脱氢残基（当分散的间隔基团是一个烷基或一个烷基和一个芳基时除外）；一个氨基酸的脱氢残基；一个卤代silyl基团；或卤代silyl基团的卤素被取代的取代silyl基团上的官能团，与(meth)allylsilyl基团键合。
• (Meth)allylsilane compound, silane coupling agent thereof, and functional material using the same
  申请人：Shimada Toyoshi

  公开号：US09228107B2

  公开（公告）日：2016-01-05

  A (meth)allylsilane compound that a functional group of a (meth)allylsilyl group or a halogenosilyl group bonded to the (meth)allylsilyl group via a spacer group is bonded directly or through a divergent spacer group to a dehydrogenated residue of an amino group of an amino group-containing compound; a carbaminic acid ester group or an amide group derived from a dehydrogenated residue of the amino group; an aromatic compound; a polymerizable unsaturated groups; perfluoro group; a dehydrogenated residue of saccharide or a carbohydrate polyol (excluding when the divergent spacer group is an alkylene group, or an alkylene group and an arylene group); a dehydrogenated residue of an amino acid; a halogenosilyl group; or a substituted silyl group in which a halogen of the halogenosilyl group is substituted.

  一种（甲基）烯丙基硅烷化合物，其中一个（甲基）烯丙基硅基团或卤代硅基团通过一个间隔基团直接或通过一个分支间隔基团与含氨基化合物的氨基残基的脱氢残基结合；一种由氨基残基的脱氢残基衍生的氨基甲酸酯基团或酰胺基团；芳香族化合物；可聚合不饱和基团；全氟基团；糖或碳水化合物多元醇的脱氢残基（当分支间隔基团为烷基或烷基和芳基时除外）；氨基酸的脱氢残基；卤代硅基团；或卤素被取代的卤代硅基团中的取代硅基团。
• Synthesis of tripod-shaped oligo(phenylene)s with multiple ethenyl groups at the bases for chemisorption on hydrogen-terminated silicon surfaces
  作者：Xiaobin Deng、Chengzhi Cai

  DOI：10.1016/s0040-4039(02)02641-2

  日期：2003.1

  This communication describes an efficient and convergent synthesis of monodisperse, nanometer-sized, and tripod-shaped oligo(phenylene)s with a triallylsilyl group at the base of each leg and a chlorophenyl group at the focal point of the tripod. These molecules were designed as model compounds for the study of chemisorption of rigid molecules containing multiple ethenyl groups on hydrogen-terminated silicon surfaces. The compounds were synthesized from p-chlorophenyl-tris(p-bromopenyl)silane via selective Pd-catalyzed Ishiyama-Miyaura reaction with bis(pinacolato)diboron, followed by Suzuki coupling with aryl dihalides to elongate the legs. The legs were then end-capped with triallylsilyl groups through Suzuki coupling with 4-triallyphenylboronic acid. (C) 2003 Elsevier Science Ltd. All rights reserved.
• An Efficient Convergent Synthesis of Novel Anisotropic Adsorbates Based on Nanometer-Sized and Tripod-Shaped Oligophenylenes End-Capped with Triallylsilyl Groups
  作者：Xiaobin Deng、Aurelie Mayeux、Chengzhi Cai

  DOI：10.1021/jo0257750

  日期：2002.7.1

  This article describes an efficient and convergent synthesis of a novel tripod-shaped oligophenylene compound. The compound consists of three oligophenylene heptamers as the tripod legs and one bromophenyl group as the functional arm, joining at a tetrahedron silicon atom. Each tripod leg is end-capped with a triallylsilyl group for covalently anchoring the molecules on hydrogen-terminated silicon

  本文介绍了一种新型的三脚架形状的低聚亚苯基化合物的有效和收敛的合成。该化合物由三个四面体硅原子上的三脚撑低聚亚苯基七聚体和三官能团一个溴苯基组成。每个三脚架腿都用三烯丙基甲硅烷基封端，以通过氢化硅烷化将分子共价锚定在氢封端的硅表面上。该化合物可以代表一种新型的各向异性吸附物，用于控制有机薄膜中官能团的取向和间距以及在硅表面上生长的纳米结构的间距。端基为三烯丙基甲硅烷基和频哪醇芳基硼酸酯基的低聚亚苯基六聚物很容易通过选择性的Suzuki偶联反应从二碘三苯基与溴苯基硼酸衍生而来。为在竞争性的Heck反应中存在多个乙烯基，开发了位阻频哪醇硼酸酯与芳基碘的高度选择性Suzuki偶联的反应条件。在最佳条件下（Pd（PPh3）4 / KOH / Bu4NBr /甲苯/ H2O，85摄氏度，过夜），对溴苯基-三（对碘苯基）硅烷与3个当量的六亚苯基硼酸酯反应生成由22个亚苯基和9个烯丙基组成的三脚架形低聚亚苯基，收率为78％。