4,4,5,5-tetramethyl-2-(5-methyl-2-phenylcyclohexa-1,4-dienyl)-1,3,2-dioxaborolane

• 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: 4,4,5,5-tetramethyl-2-(5-methyl-2-phenylcyclohexa-1,4-dienyl)-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-Tetramethyl-2-(5-methyl-2-phenylcyclohexa-1,4-dien-1-yl)-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-(5-methyl-2-phenylcyclohexa-1,4-dien-1-yl)-1,3,2-dioxaborolane
• 化学式: C₁₉H₂₅BO₂
• 分子量: 296.217
• InChiKey: SBGHBZKZWCULCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-苯基-1-乙炔硼酸频那醇酯 在 Grubbs catalyst first generation 、 正丁基锂 、 二氯二茂锆 、 三丁基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4,4,5,5-tetramethyl-2-(5-methyl-2-phenylcyclohexa-1,4-dienyl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  Synthesis of Cyclic 1-Alkenylboronates via Zr-Mediated Double Functionalization of Alkynylboronates and Sequential Ru-Catalyzed Ring-Closing Olefin Metathesis

  摘要：

  Synthesis of novel cyclic 1-alkenylboronates is accomplished through the zirconium-mediated regio- and stereoselective double functionalization of 1-alkynylboronates and the subsequent ruthenium-catalyzed ring-closing metathesis (RCM). The obtained substituted cyclic 1-alkenylboronates are transformed into o-terphenyl and triphenylene derivatives.

  DOI：

  10.1021/ol400896u

文献信息

• Alkynylboronic Esters as Efficient Dienophiles in Cobalt-Catalyzed Diels–Alder Reactions
  作者：Gerhard Hilt、Konstantin I. Smolko

  DOI：10.1002/anie.200351404

  日期：2003.6.23
• Synthesis of Cyclic 1-Alkenylboronates via Zr-Mediated Double Functionalization of Alkynylboronates and Sequential Ru-Catalyzed Ring-Closing Olefin Metathesis
  作者：Yasushi Nishihara、Masato Suetsugu、Daisuke Saito、Megumi Kinoshita、Masayuki Iwasaki

  DOI：10.1021/ol400896u

  日期：2013.5.17

  Synthesis of novel cyclic 1-alkenylboronates is accomplished through the zirconium-mediated regio- and stereoselective double functionalization of 1-alkynylboronates and the subsequent ruthenium-catalyzed ring-closing metathesis (RCM). The obtained substituted cyclic 1-alkenylboronates are transformed into o-terphenyl and triphenylene derivatives.