1,4-dimethyl-4-hydroxy-8-isopropyl-4,5-dihydrobenzo[cd]azulen-3-one | 1276114-56-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,4-dimethyl-4-hydroxy-8-isopropyl-4,5-dihydrobenzo[cd]azulen-3-one
• 英文别名: 6-Hydroxy-2,6-dimethyl-11-propan-2-yltricyclo[6.4.1.04,13]trideca-1,3,8(13),9,11-pentaen-5-one；6-hydroxy-2,6-dimethyl-11-propan-2-yltricyclo[6.4.1.04,13]trideca-1,3,8(13),9,11-pentaen-5-one
• CAS: 1276114-56-7
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: REZVAPWWHVXPBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dimethyl-4-hydroxy-8-isopropyl-4,5-dihydrobenzo[cd]azulen-3-one 在 盐酸 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.25h， 生成 8-isopropylidene-3-methoxy-1,4-dimethyl-8H-benzo[cd]azulene
  参考文献：
  名称：

  Synthesis and Tautomerization of Benzo[cd]azulen-3-ones

  摘要：

  This report describes a type of tautomerization reaction that proceeds via isomerization of pi-bonds across the azulene moieties of tricyclic benzo[cd]azulen-3-ones. The reaction mechanism shows similarities to an elimination reaction that was recently developed in our group. Furthermore, the facile four-step syntheses of the benzo[cd]azulen-3-ones, the starting materials for the tautomerization reactions, and computational analyses of the tautomerization reaction are included.

  DOI：

  10.1021/ol2001528
• 作为产物：
  描述：

  2-hydroxy-3-(7-isopropyl-1-methylazulen-4-yl)-2-methylpropionic acid 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 以80%的产率得到1,4-dimethyl-4-hydroxy-8-isopropyl-4,5-dihydrobenzo[cd]azulen-3-one
  参考文献：
  名称：

  Synthesis and Tautomerization of Benzo[cd]azulen-3-ones

  摘要：

  This report describes a type of tautomerization reaction that proceeds via isomerization of pi-bonds across the azulene moieties of tricyclic benzo[cd]azulen-3-ones. The reaction mechanism shows similarities to an elimination reaction that was recently developed in our group. Furthermore, the facile four-step syntheses of the benzo[cd]azulen-3-ones, the starting materials for the tautomerization reactions, and computational analyses of the tautomerization reaction are included.

  DOI：

  10.1021/ol2001528