ethyl 3-hydroxy-7-isopropyl-5-methyl-2-oxo-2,3-dihydro-1H-azuleno[8,1-bc]pyridine-3-carboxylate | 1279720-34-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: ethyl 3-hydroxy-7-isopropyl-5-methyl-2-oxo-2,3-dihydro-1H-azuleno[8,1-bc]pyridine-3-carboxylate
• 英文别名: Ethyl 5-hydroxy-2-methyl-6-oxo-11-propan-2-yl-7-azatricyclo[6.4.1.04,13]trideca-1,3,8(13),9,11-pentaene-5-carboxylate
• CAS: 1279720-34-1
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: BDCQGWPGIUDCRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-isopropyl-1-methylazulene-4-carboxylic acid 在 叠氮磷酸二苯酯 、 水 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 43.17h， 生成 ethyl 3-hydroxy-7-isopropyl-5-methyl-2-oxo-2,3-dihydro-1H-azuleno[8,1-bc]pyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis of 4-aminoguaiazulene and its δ-lactam derivatives

  摘要：

  A method for nitrogen insertion into guaiazulene hydrocarbons is developed. A one-pot reaction of 7-isopropyl-1-methylazulene-4-carboxylic acid, diphenylphosphoryl azide, and an alcohol (MeOH, BuOH or BnOH) affords the corresponding carbamates. Deprotection of benzyl (7-isopropyl-1-methylazulen-4-yl)carbamate under basic conditions gave 4-aminoguaiazulene, which undergoes ring annulation reactions with 1,2-dicarbonyl reagents to yield tricyclic delta-lactams. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.016

文献信息

• Synthesis of 4-aminoguaiazulene and its δ-lactam derivatives
  作者：Alexandros Kiriazis、Ingo B. Aumüller、Jari Yli-Kauhaluoma

  DOI：10.1016/j.tetlet.2011.01.016

  日期：2011.3

  A method for nitrogen insertion into guaiazulene hydrocarbons is developed. A one-pot reaction of 7-isopropyl-1-methylazulene-4-carboxylic acid, diphenylphosphoryl azide, and an alcohol (MeOH, BuOH or BnOH) affords the corresponding carbamates. Deprotection of benzyl (7-isopropyl-1-methylazulen-4-yl)carbamate under basic conditions gave 4-aminoguaiazulene, which undergoes ring annulation reactions with 1,2-dicarbonyl reagents to yield tricyclic delta-lactams. (C) 2011 Elsevier Ltd. All rights reserved.