2,6-dihydroxyazulene | 128370-12-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2,6-dihydroxyazulene
• 英文别名: 2,6-Dihydroxy-azulen；Azulene-2,6-diol
• CAS: 128370-12-7
• 化学式: C₁₀H₈O₂
• 分子量: 160.172
• InChiKey: ZEDDXZWVFLOLKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)azulene 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以50%的产率得到2,6-dihydroxyazulene
  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

• LIQUID CRYSTAL MOLECULES COMPRISING HYDROAZULENE STRUCTURES
  申请人：Tetragon-Chemie AG

  公开号：EP1896552B1

  公开（公告）日：2010-05-19
• JPH0269438A
  申请人：——

  公开号：JPH0269438A

  公开（公告）日：1990-03-08
• JPH0269437A
  申请人：——

  公开号：JPH0269437A

  公开（公告）日：1990-03-08
• JPH0269441A
  申请人：——

  公开号：JPH0269441A

  公开（公告）日：1990-03-08
• 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.