4-(triallylsilyl)phenylboronic acid | 450371-59-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-(triallylsilyl)phenylboronic acid
• 英文别名: [4-Tris(prop-2-enyl)silylphenyl]boronic acid
• CAS: 450371-59-2
• 化学式: C₁₅H₂₁BO₂Si
• 分子量: 272.227
• InChiKey: XMYBQPYYRYWTOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(triallylsilyl)phenylboronic acid 、 Tris(4-bromophenyl)-(4-chlorophenyl)silane 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以82%的产率得到(4-Chlorophenyl)-tris[4-[4-tris(prop-2-enyl)silylphenyl]phenyl]silane
  参考文献：
  名称：

  Synthesis of tripod-shaped oligo(phenylene)s with multiple ethenyl groups at the bases for chemisorption on hydrogen-terminated silicon surfaces

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)02641-2
• 作为产物：
  描述：

  对溴苯基三氯硅烷 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 生成 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

文献信息

• 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％。
• 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.