4,5-dichloro-2-heptanoylpyridazin-3(2H)-one | 1427414-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,5-dichloro-2-heptanoylpyridazin-3(2H)-one
• CAS: 1427414-27-4
• 化学式: C₁₁H₁₄Cl₂N₂O₂
• 分子量: 277.15
• InChiKey: CSDQHUQDIZEHJH-UHFFFAOYSA-N

物化性质

• 沸点：
  333.1±52.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,5-dichloro-2-heptanoylpyridazin-3(2H)-one 、 4-甲氧基苯酚 以 neat (no solvent) 为溶剂， 反应 0.17h， 以99%的产率得到(4-甲氧基苯基)庚酸酯
  参考文献：
  名称：

  Rapid and Ecofriendly Esterification of Alcohols with 2-Acylpyridazinones

  摘要：

  原子经济性的酯化反应在绿色化学中极为重要。在本研究中，我们展示了在无溶剂条件下，通过醇与2-酰基-4,5-二氯哒嗪-3(2H)-酮反应，无需催化剂和添加剂，在$100^{\circ}C$下实现醇的酯化反应。脂肪族和芳香族醇均能以良好至优异的产率转化为相应酯。值得注意的是，该反应无溶剂、原子经济性高、操作简便、反应迅速且成本低廉。

  DOI：

  10.5012/bkcs.2013.34.11.3410

文献信息

• Eco-friendly atom-economical synthesis of 2-substituted-benzo[d]thiazoles and 2-substituted-benzo[d]oxazoles using 2-acylpyridazin-3(2H)-ones
  作者：Gi Hyeon Sung、In-Hye Lee、Bo Ram Kim、Dong-Soo Shin、Jeum-Jong Kim、Sang-Gyeong Lee、Yong-Jin Yoon

  DOI：10.1016/j.tet.2013.02.093

  日期：2013.4

  Efficient and green syntheses of heterocycles are of great importance. In this work, we have demonstrated the synthesis of benzo[d]thiazoles and benzo[d]oxazoles using 2-acylpyridazin-3(2H)-ones as acyl transfer agents under transition-metal-free and eco-friendly conditions. It is worthy to note that the reaction is efficient, green, and economical, and will find several applications in organic synthesis, medicinal chemistry, and industrial chemistry. (C) 2013 Elsevier Ltd. All rights reserved.
• Catalyst-free esterification of alcohols using 2-acyl-4,5-dichloropyridazinones under microwave conditions
  作者：Bo Ram Kim、Gi Hyeon Sung、Sang-Gyeong Lee、Yong Jin Yoon

  DOI：10.1016/j.tet.2013.02.046

  日期：2013.4

  Efficient and green esterification is of great importance. In this work, we demonstrate the catalyst-free esterification of alcohols by their reaction with 2-acy1-4,5-dichloropyridazin-3(2H)-ones under microwave irradiation. Aliphatic and aromatic alcohols were converted into the corresponding esters in good to excellent yields under microwave irradiation in solvent or solvent-free conditions. It is noteworthy that the reaction is catalyst-free, atom-economic, and rapid and that the process is inexpensive. (C) 2013 Elsevier Ltd. All rights reserved.
• Facile Esterification of Alcohols with 2-Acyl-4,5-dichloropyridazin-3(2H)-ones under Friedel–Crafts Conditions
  作者：Hyo Yoon、Yong-Jin Yoon、Bo Kim、Gi Sung、Ki Ryu、Sang-Gyeong Lee

  DOI：10.1055/s-0034-1378335

  日期：——

  This paper describes the esterification of aromatic and aliphatic alcohols by using 2-acyl-4,5-dichloropyridazin-3(2H)-ones as an acyl source under Friedel Crafts conditions. Twelve alcohols were reacted with four 2-acyl-4,5-dichloropyridazin-3(2H)-ones in the presence of AlCl3 in tetrahydrofuran at room temperature to give the corresponding esters in moderate to excellent yields. Thus, 2-acylpyridazin-3(2H)-ones serve as good and atom-economic acyl sources for the esterification of aromatic alcohols under Friedel Crafts conditions, representing a rapid, practical, and efficient method of esterification.