(Z)-1-(trimethylsilyl)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene | 1512848-93-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-1-(trimethylsilyl)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene
• 英文别名: (Z)-(1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)trimethylsilane；(E)-(1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)trimethylsilane；[(Z)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-trimethylsilane
• CAS: 1512848-93-9
• 化学式: C₂₃H₃₁BO₂Si
• 分子量: 378.394
• InChiKey: HWAPXDCIQYRULL-QZQOTICOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-(trimethylsilyl)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene 在 四(三苯基膦)钯 、 一氯化碘 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 四氯化碳 、 水 为溶剂， 反应 18.0h， 生成 1-iodo-1,2,2-triphenylethene
  参考文献：
  名称：

  硼-维蒂希反应立体选择性合成硅烷化乙烯基硼酸酯及其在四取代烯烃中的应用

  摘要：

  采用硼-维蒂希法合成了一系列四取代甲硅烷基化频哪醇乙烯基硼酸酯和三取代甲硅烷基化乙烯基MIDA-硼酸酯。通过使用该方案，硼基和甲硅烷基可以直接且高度立体选择性地结合到烯烃的反位中。此外，硅烷化乙烯基硼酸酯的连续 Suzuki 偶联可以得到几种全碳四取代烯烃、抗癌药物他莫昔芬和 AIEgen 试剂 TPE-TF17。

  DOI：

  10.1002/chem.202303056
• 作为产物：
  描述：

  联硼酸频那醇酯 在 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) 、 四(三苯基膦)铂 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 3.0h， 生成 (Z)-1-(trimethylsilyl)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene
  参考文献：
  名称：

  Selective Synthesis of Multisubstituted Olefins Utilizing gem- and vic-Diborylated Vinylsilanes Prepared by Silylborylation of an Alkynylboronate and Diborylation of Alkynylsilanes

  摘要：

  The synthesis of a series of gem- and vic-diborylated vinylsilanes was accomplished via highly selective transition-metal-catalyzed syn-dimetalation to the alkynylmetal species. This protocol served as a general synthetic method toward regio- and stereodefined multisubstituted olefins. The key steps are the diastereoselective Suzuki-Miyaura cross-coupling reactions of gem- and vic-diborylated vinylsilanes, in which the two boron groups showed discrete reactivities to afford diverse precursors of multisubstituted olefins.

  DOI：

  10.1021/jo4024057

文献信息

• Selective Synthesis of Multisubstituted Olefins Utilizing <i>gem</i>- and <i>vic</i>-Diborylated Vinylsilanes Prepared by Silylborylation of an Alkynylboronate and Diborylation of Alkynylsilanes
  作者：Jiao Jiao、Keita Hyodo、Hao Hu、Kiyohiko Nakajima、Yasushi Nishihara

  DOI：10.1021/jo4024057

  日期：2014.1.3

  The synthesis of a series of gem- and vic-diborylated vinylsilanes was accomplished via highly selective transition-metal-catalyzed syn-dimetalation to the alkynylmetal species. This protocol served as a general synthetic method toward regio- and stereodefined multisubstituted olefins. The key steps are the diastereoselective Suzuki-Miyaura cross-coupling reactions of gem- and vic-diborylated vinylsilanes, in which the two boron groups showed discrete reactivities to afford diverse precursors of multisubstituted olefins.
• Stereoselective Synthesis of Silylated Vinylboronates by a Boron‐Wittig Reaction and Their Application to Tetrasubstituted Olefins
  作者：Subrata Hazra、Santanu Panda

  DOI：10.1002/chem.202303056

  日期：2024.2.12

  series of tetrasubstituted silylated pinacol vinylboronates and trisubstituted silylated vinyl MIDA-boronates was synthesized by using the boron-Wittig approach. By using this protocol, the boryl and the silyl groups can be directly and highly stereoselectively incorporated into the olefin‘s anti-position. Further, sequential Suzuki coupling of the silylated vinyl boronates allows access to several

  采用硼-维蒂希法合成了一系列四取代甲硅烷基化频哪醇乙烯基硼酸酯和三取代甲硅烷基化乙烯基MIDA-硼酸酯。通过使用该方案，硼基和甲硅烷基可以直接且高度立体选择性地结合到烯烃的反位中。此外，硅烷化乙烯基硼酸酯的连续 Suzuki 偶联可以得到几种全碳四取代烯烃、抗癌药物他莫昔芬和 AIEgen 试剂 TPE-TF17。