methyl 2-(azulen-6-yl)acetate | 26156-73-0

• 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 2-(azulen-6-yl)acetate
• 英文别名: Methyl-6-azulylacetat；Methyl 2-azulen-6-ylacetate
• CAS: 26156-73-0
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: OXSZFSYBHOWINA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-(azulen-6-yl)acetate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.25h， 生成 (6-methylazulen-1-yl)[4-(trifluoromethyl)phenyl]methanone
  参考文献：
  名称：

  Azulene-based compounds for targeting orexin receptors

  摘要：

  A library of 70 000 synthetically accessible azulene-based compounds was virtually screened at the OX2 receptor. Based on the results, a series of azulene derivatives was synthesized and the binding to and activation of both orexin receptor subtypes were assessed. Two most promising binders were determined to have inhibition constants in the 3-9 mu M range and two other compounds showed weak OX2 receptor agonism. Furthermore, three compounds exhibited a concentration-dependent potentiation of the response to orexin-A at the OX1 but not the OX2 receptors. Altogether this data opens new approaches for further development of antagonists, agonists, and potentiators of orexin response based on the azulene scaffold. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.040
• 作为产物：
  描述：

  6-methylazulene 以 乙醚 为溶剂， 生成 methyl 2-(azulen-6-yl)acetate
  参考文献：
  名称：

  Nonbenzenoid aromatic systems. VIII. Buffered acetolysis of 2-(4- and 2-(6-azulyl)ethyl arenesulfonates and 3-(4-azulyl)-1-propyl nosylate. Examples of Ar3-5 and Ar3-6 mechanisms

  摘要：

  DOI：

  10.1021/jo00946a010

文献信息

• Jutz,C.; Schweiger,E., Chemische Berichte, 1974, vol. 107, p. 2383 - 2396
  作者：Jutz,C.、Schweiger,E.

  DOI：——

  日期：——
• Azulene-based compounds for targeting orexin receptors
  作者：Teppo O. Leino、Ainoleena Turku、Jari Yli-Kauhaluoma、Jyrki P. Kukkonen、Henri Xhaard、Erik A.A. Wallén

  DOI：10.1016/j.ejmech.2018.07.040

  日期：2018.9

  A library of 70 000 synthetically accessible azulene-based compounds was virtually screened at the OX2 receptor. Based on the results, a series of azulene derivatives was synthesized and the binding to and activation of both orexin receptor subtypes were assessed. Two most promising binders were determined to have inhibition constants in the 3-9 mu M range and two other compounds showed weak OX2 receptor agonism. Furthermore, three compounds exhibited a concentration-dependent potentiation of the response to orexin-A at the OX1 but not the OX2 receptors. Altogether this data opens new approaches for further development of antagonists, agonists, and potentiators of orexin response based on the azulene scaffold. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Nonbenzenoid aromatic systems. VIII. Buffered acetolysis of 2-(4- and 2-(6-azulyl)ethyl arenesulfonates and 3-(4-azulyl)-1-propyl nosylate. Examples of Ar3-5 and Ar3-6 mechanisms
  作者：Richard N. McDonald、N. Lee Wolfe、Herbert E. Petty

  DOI：10.1021/jo00946a010

  日期：1973.3