2-(3-methylbenzofuran-2-yl)-4H-benzo[d][1,3]oxazin-4-one | 1186680-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-(3-methylbenzofuran-2-yl)-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 2-(3-methylbenzofuran-2-yl)-4H-3,1-benzoxazin-4-one；2-(3-Methyl-1-benzofuran-2-yl)-3,1-benzoxazin-4-one
• CAS: 1186680-36-3
• 化学式: C₁₇H₁₁NO₃
• 分子量: 277.279
• InChiKey: PGFJCINGPAVRJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-iodophenyl)-3-methyl-1-benzofuran-2-carboxamide 、 甲酸苯酯 在 二(氰基苯)二氯化钯 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以80%的产率得到2-(3-methylbenzofuran-2-yl)-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  以甲酸苯酯为一氧化碳源羰基化合成邻苯二甲酰亚胺和苯并恶嗪酮

  摘要：

  通过使用甲酸苯酯作为 CO 源，研究了一种简单有效的钯催化的 N-取代 2-碘苯甲酰胺和 2-碘苯胺的羰基化环化反应，分别用于合成邻苯二甲酰亚胺和苯并嗪酮。本催化协议在邻苯二甲酰亚胺合成的情况下避免使用昂贵的膦配体以及溶剂。此外，温和的反应条件和对各种官能团的耐受性增强了该方法的普遍适用性。

  DOI：

  10.1002/ejoc.201500109

文献信息

• Convenient synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives
  作者：Hatem A. Abdel-Aziz、Amal A.I. Mekawey、Kamal M. Dawood

  DOI：10.1016/j.ejmech.2009.02.020

  日期：2009.9

  The reaction of 3-methylbenzofuran-2-carbohydrazide (1) with 1-phenyl-2-bromoethanone (2a) or 2-chloro-1-(4-chlorophenyl)ethanone (2b) afforded (Z)-1,2-di[(3-methylbenzofuran-2-carbohydrazido]-1-arylethenes Sa and 5b, respectively. Single crystal X-ray analyses of compound 5a proved that the reaction proceeds in 2:1 molar ratio and ruled out the other possible structures 1,3,4-oxadiazine derivative 6 or E-isomer 7. Furthermore, both of 3-(3-methylbenzofuran-2-yl)-3-oxopropanenitrile (9) and 3-methyl-2-benzofuranoyl chloride (15) were used as starting materials for the synthesis of several compounds, such as pyrazoles 10 and 14, oxime 11, hydrazones 12a, b and 3,1-bezoxazine 19. The newly synthesized compounds were tested for their antimicrobial activity against five fungal species and four bacterial species also their minimum inhibitory concentration (MIC) against most of test organisms was performed. Some of these compounds exhibited a significant antimicrobial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Carbonylative Synthesis of Phthalimides and Benzoxazinones by Using Phenyl Formate as a Carbon Monoxide Source
  作者：Sujit P. Chavan、Bhalchandra M. Bhanage

  DOI：10.1002/ejoc.201500109

  日期：2015.4

  efficient palladium-catalyzed carbonylative cyclization of N-substituted 2-iodobenzamides and 2-iodoanilides was investigated for the synthesis of phthalimides and benzoxazinones, respectively, by using phenyl formate as a CO source. The present catalytic protocol circumvents the use of an expensive phosphine ligand as well as solvent in the case of the phthalimide synthesis. Moreover, mild reaction conditions

  通过使用甲酸苯酯作为 CO 源，研究了一种简单有效的钯催化的 N-取代 2-碘苯甲酰胺和 2-碘苯胺的羰基化环化反应，分别用于合成邻苯二甲酰亚胺和苯并嗪酮。本催化协议在邻苯二甲酰亚胺合成的情况下避免使用昂贵的膦配体以及溶剂。此外，温和的反应条件和对各种官能团的耐受性增强了该方法的普遍适用性。