2-(2,2-Dinaphthalen-1-ylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 801301-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2,2-Dinaphthalen-1-ylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-(2,2-dinaphthalen-1-ylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 801301-74-6
• 化学式: C₂₈H₂₇BO₂
• 分子量: 406.332
• InChiKey: MRNIFTOBDZSCJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  1-溴-3-苯基丙烷 、 2-(2,2-Dinaphthalen-1-ylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 palladium diacetate sodium hydroxide 、 二叔丁基甲基膦 作用下， 以 1,4-二氧六环 为溶剂， 以58%的产率得到
  参考文献：
  名称：

  Versatile Synthesis of 1,1-Diaryl-1-alkenes Using Vinylboronate Ester as a Platform

  摘要：

  乙烯硼酸频哪醇酯与芳基卤化物发生一系列双 Mizoroki-Heck 反应，然后由此产生的 β,β-二芳基乙烯硼酸酯与烷基卤化物发生 Suzuki-Miyaura 偶联反应，可非常有效地生成具有重要药用价值的 1,1-二芳基-1-烯烃。在由钯催化的 Suzuki-Miyaura 偶联反应步骤中，使用体积较大的富电子配体（如 P(t-Bu)2Me 和 PCy2(t-Bu)）非常有效。

  DOI：

  10.1055/s-2005-871539
• 作为产物：
  描述：

  1-碘萘 、 乙烯基硼酸频哪醇酯 在 bis(tri-tert-butylphosphine)palladium(0) 二异丙胺 作用下， 以 甲苯 为溶剂， 以63%的产率得到2-(2,2-Dinaphthalen-1-ylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Rapid Construction of Multisubstituted Olefin Structures Using Vinylboronate Ester Platform Leading to Highly Fluorescent Materials

  摘要：

  A catalytic one-pot triarylation on the C=C core of vinylboronate pinacol ester (1) produces extended T-systems based on a multisubstituted olefin structure very rapidly. We established an efficient protocol for the Pd-catalyzed double C-H arylation of 1 with aryl halides, which was successfully integrated with C-B arylation with aryl halides (cross-coupling) in one pot. By using this method, several highly fluorescent materials with a wide range of color variations (blue to red) were discovered.

  DOI：

  10.1021/ol048217b

文献信息

• Rapid Construction of Multisubstituted Olefin Structures Using Vinylboronate Ester Platform Leading to Highly Fluorescent Materials
  作者：Kenichiro Itami、Keisuke Tonogaki、Youichi Ohashi、Jun-ichi Yoshida

  DOI：10.1021/ol048217b

  日期：2004.10.1

  A catalytic one-pot triarylation on the C=C core of vinylboronate pinacol ester (1) produces extended T-systems based on a multisubstituted olefin structure very rapidly. We established an efficient protocol for the Pd-catalyzed double C-H arylation of 1 with aryl halides, which was successfully integrated with C-B arylation with aryl halides (cross-coupling) in one pot. By using this method, several highly fluorescent materials with a wide range of color variations (blue to red) were discovered.
• Versatile Synthesis of 1,1-Diaryl-1-alkenes Using Vinylboronate Ester as a Platform
  作者：Kenichiro Itami、Jun-ichi Yoshida、Keisuke Tonogaki、Kazuya Soga

  DOI：10.1055/s-2005-871539

  日期：——

  A sequence of double Mizoroki-Heck reaction of vinylboronate pinacol ester with aryl halides followed by Suzuki-Miyaura coupling of thus-generated β,β-diarylvinylboronate esters with alkyl halides produces pharmaceutically important 1,1-diaryl-1-alkenes very efficiently. In the Pd-catalyzed Suzuki-Miyaura coupling step, the use of bulky electron-rich ligands such as P(t-Bu)2Me and PCy2(t-Bu) were found to be very effective.

  乙烯硼酸频哪醇酯与芳基卤化物发生一系列双 Mizoroki-Heck 反应，然后由此产生的 β,β-二芳基乙烯硼酸酯与烷基卤化物发生 Suzuki-Miyaura 偶联反应，可非常有效地生成具有重要药用价值的 1,1-二芳基-1-烯烃。在由钯催化的 Suzuki-Miyaura 偶联反应步骤中，使用体积较大的富电子配体（如 P(t-Bu)2Me 和 PCy2(t-Bu)）非常有效。