2,5,7-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)azulene | 1187945-47-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2,5,7-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)azulene
• 英文别名: 2-[2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)azulen-5-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)azulen-5-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1187945-47-6
• 化学式: C₂₈H₄₁B₃O₆
• 分子量: 506.063
• InChiKey: RGBVLWXNCVKNKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)azulene 、 联硼酸频那醇酯 在 2,2'-联吡啶 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 作用下， 以 环己烷 为溶剂， 以20%的产率得到2,5,7-tris(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

文献信息

• Polyborylation of azulenes
  作者：Masayuki Fujinaga、Toshihiro Murafuji、Kei Kurotobi、Yoshikazu Sugihara

  DOI：10.1016/j.tet.2009.06.053

  日期：2009.8

  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.