1,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)azulene | 1187945-61-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)azulene
• CAS: 1187945-61-4
• 化学式: C₂₂H₃₀B₂O₄
• 分子量: 380.1
• InChiKey: PEIUYFVYBUNEEK-UHFFFAOYSA-N

物化性质

• 熔点：
  193-194 °C
• 沸点：
  503.3±23.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  联硼酸频那醇酯 、 2-(1-azulenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane 在 4,4'-二甲基-2,2'-联吡啶 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 环己烷 为溶剂， 以9%的产率得到1,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)azulene
  参考文献：
  名称：

  Polyborylation of azulenes

  摘要：

  In the presence of an active Ir-based catalyst, azulene underwent stepwise borylation with bis(pinacolato)diboron to produce polyborylated products. The reactivity of the ring atoms toward borylation was found to decrease in the following order: 2-position>1,3-positiotls>6-position>5,7-positions. Extension of the borylation to some azulenes Substituted at the five-membered ring was also examined. Furthermore, the reaction of 2,6-bis(4,4,5.5-tetramethyl-1,3,2-dioxaborolanyl)azulene (3a) with an equivalent of hydrogen peroxide revealed that the oxidation proceeds preferentially at the 6-position. This indicates that the reactivity of the boryl group is governed by the pi-polarization of the azulenyl skeleton. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.06.053