p-tolyl-2 <4H> benzoxazine-1,3 one-4 | 25225-62-1

• 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: p-tolyl-2 <4H> benzoxazine-1,3 one-4
• 英文别名: 2-(4-methylphenyl)-1,3-benzoxazin-4-one；2-(p-tolyl)-4H-benzo[e][1,3]oxazin-4-one；2-(4'-Methylphenyl)-4H-1,3-benzoxazin-4-on；2-p-tolyl-benzo[e][1,3]oxazin-4-one；2-p-tolyl-benz[e][1,3]oxazin-4-one；2-p-Tolyl-benz[e][1,3]oxazin-4-on；2-(p-tolyl)benz-(4H)-1,3-oxazin-4-one
• CAS: 25225-62-1
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: IIGYEVFLZBMDAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  113 °C(Solv: ligroine (8032-32-4))
• 沸点：
  389.3±35.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  p-tolyl-2 <4H> benzoxazine-1,3 one-4 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以64%的产率得到2-(3-(p-tolyl)-1,2,4-oxadiazol-5-yl)phenol
  参考文献：
  名称：

  Antimicrobial effects of novel siderophores linked to β-lactam antibiotics

  摘要：

  As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-P-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00261-8
• 作为产物：
  描述：

  水杨酰胺 在 吡啶 、 四磷十氧化物 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 丙酮 为溶剂， 生成 p-tolyl-2 <4H> benzoxazine-1,3 one-4
  参考文献：
  名称：

  钯催化C（sp2）-H的电化学氧化羟化反应合成2-（2-羟基芳基）-4H-苯并[e] [1,3]恶嗪-4-酮

  摘要：

  以Pd（OAc）2为催化剂，恶嗪环为导向基团和Oxone为羟基化作用开发了2-芳基-4 H-苯并[ e ] [1,3]恶嗪-4-酮的电化学直接邻羟基化反应试剂。在温和条件下获得了一系列羟基化产物，收率从中等到良好。该方法的特征在于良好的官能团耐受性和广泛的底物。更重要的是，使用阳极氧化以避免使用潜在的有毒和污染性氧化剂。的2-苯基-4-甲克级直接电化学羟化ħ苯并[ ë进行] [1,3]恶嗪-4-酮的合成，并应用羟基化产物合成地拉罗司。另外，获得了2-（2-羟基苯基）-4- H-苯并[ e ] [1,3]恶嗪-4-酮的单晶并通过X射线衍射测定。最后，提出了反应机理并通过循环伏安法（CV）进行了验证。该协议还提供了分子功能化的另一种电化学羟基化方法。

  DOI：

  10.1002/adsc.202000173

文献信息

• Chemoselective Reaction of Benzoylisothiocyanates with Hydroxyl Group of Salicylamide: a New and Convenient Entry Into 2-Aryl-4<i>H</i>-benzo[e][1,3]oxazin-4-ones
  作者：Tarjeet Singh、Girija S. Singh、Ram Lakhan

  DOI：10.1080/10426507.2012.755974

  日期：2013.10.1

  Abstract The reactions of benzoylisothiocyanates with salicylamide in pyridine-xylene solution occurs chemoselectively at the hydroxyl group of the salicylamide to afford the corresponding O-benzoyl derivatives. The latter products, on prolonged heating in pyridine-xylene solution, undergo cyclodehydration to give 2-aryl-4H-benzo[e][1,3]oxazin-4-ones in good yields. These compounds could also be synthesized

  摘要 在吡啶-二甲苯溶液中，苯甲酰异硫氰酸酯与水杨酰胺在水杨酰胺的羟基上发生化学选择性反应，得到相应的O-苯甲酰衍生物。后一种产物在吡啶-二甲苯溶液中长时间加热后，会发生环脱水反应，以良好的收率得到 2-芳基-4H-苯并[e][1,3]恶嗪-4-酮。这些化合物也可以通过苯甲酰异硫氰酸酯与水杨酰胺的直接一锅反应合成，方法是在回流下将苯甲酰异硫氰酸酯缓慢加入水杨酰胺在二甲苯-吡啶溶液中的溶液中。产品已在令人满意的分析和光谱数据的基础上进行了表征。图形概要
• Babin, Pierre; Clin, Bernard; Dunogues, Jacques, Bulletin de la Societe Chimique de France, 1987, # 6, p. 997 - 1000
  作者：Babin, Pierre、Clin, Bernard、Dunogues, Jacques

  DOI：——

  日期：——
• Experiments with 2-Aryl-1,3-benzoxaz-4-ones and with 2-Phenyl-2,3-dihydro-1,3-benzoxaz-4-one. A New Type of Thermochromic Compounds
  作者：Ahmed Mustafa、Alaa Eldin、Abdel Aziz Hassan

  DOI：10.1021/ja01571a059

  日期：1957.7
• BABIN, PIERRE;CLIN, BERNARDO;DUNOGUES, JACQUES, BULL. SOC. CHIM. FR.,(1987) N 6, 997-1000
  作者：BABIN, PIERRE、CLIN, BERNARDO、DUNOGUES, JACQUES

  DOI：——

  日期：——
• HETEROCYCLISCHE VERBINDUNGEN ALS BLEICHAKTIVATOREN ODER OPTISCHE AUFHELLER IN WASCHMITTELN
  申请人：BASF Aktiengesellschaft

  公开号：EP0502013A1

  公开（公告）日：1992-09-09