4-Cyanobenz-2'-hydroxyanilid | 76284-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Cyanobenz-2'-hydroxyanilid
• 英文别名: 4-cyano-N-(2-hydroxyphenyl)benzamide
• CAS: 76284-81-6
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: OLTHLSRRWJDZLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Cyanobenz-2'-hydroxyanilid 在 盐酸 作用下， 反应 6.0h， 生成 methyl 4-(1,3-benzoxazol-2-yl)benzenecarboximidate;hydrochloride
  参考文献：
  名称：

  Wagner; Eppner, Pharmazie, 1980, vol. 35, # 5-6, p. 285 - 288

  摘要：

  DOI：
• 作为产物：
  描述：

  对氰基苯甲酰氯 、 2-氨基苯酚 在 吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 0.33h， 以91%的产率得到4-Cyanobenz-2'-hydroxyanilid
  参考文献：
  名称：

  使用氨基导向基团的铁 (III) 介导的酚类亲核卤化

  摘要：

  在 Fe(III) 试剂的存在下，实现了富电子氨基酚的酰胺定向区域选择性和亲核卤化反应。卤化物可以依次引入特定位置以形成单卤代、二卤代和混合二卤代氨基酚，主要以一锅法的方式进行。

  DOI：

  10.1002/ejoc.202200387

文献信息

• Synthesis of 2-arylbenzoxazoles via the palladium-catalyzed carbonylation and condensation of aromatic halides and o-aminophenols
  作者：Robert J. Perry、B. David Wilson、Richard J. Miller

  DOI：10.1021/jo00036a025

  日期：1992.5

  A new synthetic method is reported in which 2-arylbenzoxazoles can be prepared by the palladium-catalyzed condensation of aryl halides with o-aminophenols followed by dehydrative cyclization. This method is tolerant of a wide variety of functional groups on either aromatic ring and gives good to excellent yields of products. An aliphatic vicinal amino alcohol gave a bis-acylated product as well as a chlorine-containing product with only a small amount of the desired 2-aryloxazole being formed. Methyl iodide and benzyl bromide gave only alkylated products.
• A green route for the synthesis of 2-substituted benzoxazole derivatives catalyzed by Al3+-exchanged K10 clay
  作者：Dhanusu Suresh、Amarajothi Dhakshinamoorthy、Kasi Pitchumani

  DOI：10.1016/j.tetlet.2013.09.039

  日期：2013.11

  A new, simple, and efficient protocol is developed for the synthesis of 2-substituted benzoxazole derivatives through N-C-O bond formation using Al3+-exchanged K10 clay (Al3+-K10) as catalyst. A wide range of benzoxazole derivatives are synthesized in high yields without affecting many functional groups. Hot filtration experiments showed the absence of metal leaching and catalyst can be reused for five times with only a slight decrease in yield. (C) 2013 Elsevier Ltd. All rights reserved.
• WAGNER G.; EPPNER B., PHARMAZIE, 1980, 35, NO 5-6, 285-288
  作者：WAGNER G.、 EPPNER B.

  DOI：——

  日期：——
• Wagner; Eppner, Pharmazie, 1980, vol. 35, # 5-6, p. 285 - 288
  作者：Wagner、Eppner

  DOI：——

  日期：——
• Iron(III)‐Mediated Nucleophilic Halogenation of Phenols Using an Amido Directing Group
  作者：Ye Yuan、Dou Guo、Yibo Liu、Congcong Wan、Dongbiao Lu、Hongxiang Yang、Yufan Lu、Wei Meng、Hongling Wang、Xiang Zhang

  DOI：10.1002/ejoc.202200387

  日期：2022.5.6

  An amido-directing regioselective and nucleophilic halogenation reaction of electron-rich amidophenols was realized in the presence of Fe(III) reagents. Halides could be sequentially introduced to specific positions to form mono-, di- and mixed di- halogenated amidophenols mostly in one-pot manner.

  在 Fe(III) 试剂的存在下，实现了富电子氨基酚的酰胺定向区域选择性和亲核卤化反应。卤化物可以依次引入特定位置以形成单卤代、二卤代和混合二卤代氨基酚，主要以一锅法的方式进行。