methyl 5-isopropyl-2-hydroxyazulene-1-carboxylate | 175720-32-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: methyl 5-isopropyl-2-hydroxyazulene-1-carboxylate
• CAS: 175720-32-8
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: SZIZDMYEAPCJMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 5-isopropyl-2-hydroxyazulene-1-carboxylate 在 硝酸 、 乙酸酐 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 6.17h， 生成 5-Isopropyl-2-methoxy-3-nitro-azulene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Diazotization of Methyl 3-Amino-7-Isopropyl-2-Methoxyazulene-1-Carboxylate and its 5-Isopropyl Isomer- a Convenient Synthesis of 1,2-Azulenequinone Derivatives

  摘要：

  AbstractMethyl 3‐amino‐2‐methoxy‐7‐isopropylazulene‐l‐carboxylate(8a) and its 5‐isopropyl isomer (8b) were synthesized by reduction of the 3‐nitro derivatives (7a,b) with zinc/acetic acid in excellent yields. 7a and 7b were prepared by nitration and methylation of methyl 7‐isopropyl‐2‐hydroxyazulene‐l‐carboxylate (5a) and methyl 5‐isopropyl‐2‐hydroxyazulene‐l‐carboxylate (5b), respectively. Diazotization of 8a with sodium nitrite in trifluoroacetic acid at 0 °C gave methyl 5‐isopropyl‐1,2‐azulenequinone‐3‐carboxylate (9a) in 91% yield. Similar reaction of 8b gave the corresponding methyl 7‐isopropyl‐1,2‐azulenequinone‐3‐carboxylate (9b) in 93% yield. No evidence for the formation of l‐diazo‐1,2‐azulenequinones was obtained.

  DOI：

  10.1002/jccs.199600007
• 作为产物：
  描述：

  dimethyl 2-hydroxy-5-isopropylazulene-1,3-dicarboxylate 在 PPA 作用下， 反应 0.17h， 以42%的产率得到methyl 7-isopropyl-2-hydroxyazulene-1-carboxylate
  参考文献：
  名称：

  Diazotization of Methyl 3-Amino-7-Isopropyl-2-Methoxyazulene-1-Carboxylate and its 5-Isopropyl Isomer- a Convenient Synthesis of 1,2-Azulenequinone Derivatives

  摘要：

  AbstractMethyl 3‐amino‐2‐methoxy‐7‐isopropylazulene‐l‐carboxylate(8a) and its 5‐isopropyl isomer (8b) were synthesized by reduction of the 3‐nitro derivatives (7a,b) with zinc/acetic acid in excellent yields. 7a and 7b were prepared by nitration and methylation of methyl 7‐isopropyl‐2‐hydroxyazulene‐l‐carboxylate (5a) and methyl 5‐isopropyl‐2‐hydroxyazulene‐l‐carboxylate (5b), respectively. Diazotization of 8a with sodium nitrite in trifluoroacetic acid at 0 °C gave methyl 5‐isopropyl‐1,2‐azulenequinone‐3‐carboxylate (9a) in 91% yield. Similar reaction of 8b gave the corresponding methyl 7‐isopropyl‐1,2‐azulenequinone‐3‐carboxylate (9b) in 93% yield. No evidence for the formation of l‐diazo‐1,2‐azulenequinones was obtained.

  DOI：

  10.1002/jccs.199600007