5-Isopropyl-2-methoxy-3-nitro-azulene-1-carboxylic acid methyl ester | 175720-36-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 5-Isopropyl-2-methoxy-3-nitro-azulene-1-carboxylic acid methyl ester
• CAS: 175720-36-2
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: NKZRVVAAEUTCJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-Isopropyl-2-methoxy-3-nitro-azulene-1-carboxylic acid methyl ester 在 溶剂黄146 、 锌 作用下， 反应 0.33h， 生成 methyl 3-amino-5-isopropyl-2-methoxy-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
• 作为产物：
  描述：

  dimethyl 2-hydroxy-5-isopropylazulene-1,3-dicarboxylate 在 PPA 、 硝酸 、 乙酸酐 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 6.34h， 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

文献信息

• Diazotization of Methyl 3-Amino-7-Isopropyl-2-Methoxyazulene-1-Carboxylate and its 5-Isopropyl Isomer- a Convenient Synthesis of 1,2-Azulenequinone Derivatives
  作者：Tian-Chyuan Huang、Yun-Shan Lin、Shih-Jue Lin、Shu-Fan Chu

  DOI：10.1002/jccs.199600007

  日期：1996.2

  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.