3-(1,6-dihydroazulenyl)cyclohexan-1-one

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3-(1,6-dihydroazulenyl)cyclohexan-1-one
• 英文别名: 3-(1,6-Dihydroazulen-6-yl)cyclohexan-1-one；3-(1,6-dihydroazulen-6-yl)cyclohexan-1-one
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: ALQPYZQCVGWBPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(1,6-dihydroazulenyl)cyclohexan-1-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 0.83h， 以78%的产率得到3-(6-azulenyl)-cyclohexan-1-one
  参考文献：
  名称：

  Regioselective coupling reaction of azulene with α,β-unsaturated ketones by Mg-promoted reduction

  摘要：

  Mg-Promoted reductive coupling of azulene with various alpha,beta-unsaturated ketones in the presence of chlorotrimethylsilane in 1-methyl-2-pyrrolidinone brought about regioselective formation of the corresponding 6-substituted dihydroazulenes, which were easily oxidized to the corresponding 6-substituted azulenes by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in good yields. This new regioselective method enabled us to synthesize various 6-substituted azulenes from azulene in only two steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.080
• 作为产物：
  描述：

  2-环己烯-1-酮 、 奥苷菊环 在 三甲基氯硅烷 、 magnesium 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以49%的产率得到3-(1,6-dihydroazulenyl)cyclohexan-1-one
  参考文献：
  名称：

  Regioselective coupling reaction of azulene with α,β-unsaturated ketones by Mg-promoted reduction

  摘要：

  Mg-Promoted reductive coupling of azulene with various alpha,beta-unsaturated ketones in the presence of chlorotrimethylsilane in 1-methyl-2-pyrrolidinone brought about regioselective formation of the corresponding 6-substituted dihydroazulenes, which were easily oxidized to the corresponding 6-substituted azulenes by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in good yields. This new regioselective method enabled us to synthesize various 6-substituted azulenes from azulene in only two steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.080

文献信息

• Regioselective coupling reaction of azulene with α,β-unsaturated ketones by Mg-promoted reduction
  作者：Hirofumi Maekawa、Junya Honda、Ryoichi Akaba

  DOI：10.1016/j.tetlet.2012.09.080

  日期：2012.11

  Mg-Promoted reductive coupling of azulene with various alpha,beta-unsaturated ketones in the presence of chlorotrimethylsilane in 1-methyl-2-pyrrolidinone brought about regioselective formation of the corresponding 6-substituted dihydroazulenes, which were easily oxidized to the corresponding 6-substituted azulenes by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in good yields. This new regioselective method enabled us to synthesize various 6-substituted azulenes from azulene in only two steps. (C) 2012 Elsevier Ltd. All rights reserved.