7-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one | 40728-69-6

• 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: 7-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 7-Chloro-2-p-tolyl-benzo[d][1,3]oxazin-4-one；7-chloro-2-(4-methylphenyl)-3,1-benzoxazin-4-one
• CAS: 40728-69-6
• 化学式: C₁₅H₁₀ClNO₂
• 分子量: 271.703
• InChiKey: RRJLRMAQHMFYPK-UHFFFAOYSA-N

物化性质

• 沸点：
  399.9±31.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 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：
  3

反应信息

• 作为反应物：
  描述：

  7-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 C₁₅H₁₂ClN₃O
  参考文献：
  名称：

  Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents

  摘要：

  To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. All the synthesized compounds were evaluated for their diuretic (by Lipschitz et al. method), antihypertensive activity by non-invasive blood pressure (NIBP) using the tail-cuff method and anti-diabetic potential in rats. Six compounds showing significantly excellent activity were compared with metolazone, prazosin and diazoxide as standards. Compound N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4 nitrobenzenesulfonamide (20) exhibited most potent of the series.

  DOI：

  10.3109/14756366.2013.845820
• 作为产物：
  描述：

  在 1,1,3,3-四甲基二硅氧烷 、 copper(II) bis(trifluoromethanesulfonate) 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以85%的产率得到7-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  酸酐的催化氮杂-Wittig反应合成4 H-苯并[ d ] [1,3]恶嗪-4-酮和4-苄叉基-2-芳基恶唑-5（4 H）-酮

  摘要：

  与醛，酮，酰胺和酯的aza-Wittig反应相比，酸酐的aza-Wittig反应总是被忽略，这应该是Wittig反应的重要组成部分。在这里，酸酐的aza-Wittig反应和酸酐的aza-Wittig催化反应均以高收率开发，这为合成4 H-苯并[ d ] [1,3]恶嗪-4-酮和4-亚苄基-2-芳基恶唑-5（4 H）-那些。使用了铜催化的氧化膦还原的策略，发现该策略对这种转化有效。另外，实现了羧酸的一锅催化的氮杂-维蒂希反应。此外，NMR实验和Hammett曲线记录了酸酐的催化氮杂-维蒂希反应过程，这直接证明了铜催化的废氧化膦的还原是该转化过程中的关键步骤。

  DOI：

  10.1021/acscatal.6b00165

文献信息

• Retracted: Palladium‐Catalyzed Decarboxylative Selective Acylation of 4 <i>H</i> ‐Benzo[ <i>d</i> ][1,3]oxazin‐4‐one Derivatives with α‐Oxo Carboxylic acids <i>via</i> Preferential Cyclic Imine‐ <i>N</i> ‐Directed Aryl C−H Activation
  作者：Biju Majhi、Debasish Kundu、Tubai Ghosh、Brindaban C. Ranu

  DOI：10.1002/adsc.201500786

  日期：2016.1.21

  much interest as they are found in a large array of natural products and pharmaceutical drugs with diverse activities. We have developed a palladium‐catalyzed decarboxylative selective mono‐ and bis‐acylation of 4H‐benzo[d][1,3]oxazin‐4‐one derivatives with α‐oxo carboxylic acids via preferential cyclic imine‐N‐directed CH activation. 2‐Aryl‐4H‐benzo[d][1,3]oxazin‐4‐one was acylated with a variety

  苯并恶嗪支架引起了人们的极大兴趣，因为它们存在于多种具有多种活性的天然产物和药物中。我们已经开发了钯-催化的脱羧的选择性单-和4之二酰化ħ -苯并[ d ] [1,3]恶嗪-4-酮衍生物与α氧代羧酸经由优惠环状亚胺Ñ -directedÇ  H激活。2-芳基-4 H-苯并[ d ] [1,3]恶嗪-4-酮被各种取代的苯乙醛酸酰化，生成相应的产物。观察到给电子基团（CH 3，OCH 3）苯乙醛酸芳香环的任何位置均可提供良好的优异收率，而含有吸电子基团（COCH 3，CN，NO 2）的苯乙醛酸则可提供中等收率的产物。有趣的是，当在4当量乙醛酸存在下用三氟甲磺酸银（AgOTf）代替硝酸银（AgNO 3）进行反应时，会得到双酰化产物和少量单酰化产物。这是2-芳基-4-酰化的第一报告ħ -苯并[ d ] [1,3]恶嗪-4-酮通过Ç H激活。该反应的显着特征是与更具挑战性的杂芳烃-氧代羧酸和烷基
• Pd‐Catalyzed Carbonylative Synthesis of 4 <i>H</i> ‐Benzo[ <i>d</i> ][1,3]Oxazin‐4‐Ones Using Benzene‐1,3,5‐Triyl Triformate as the CO Source
  作者：Yan Zheng、Mengke Dong、Erdong Qu、Jin Bai、Xiao‐Feng Wu、Wanfang Li

  DOI：10.1002/chem.202103137

  日期：2021.11.22

  A Pd-catalyzed CO-free carbonylative synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives was developed. This new method employed readily available N-(o-bromoaryl)amides as the starting materials and inexpensive benzene-1,3,5-triyl triformate (TFBen) as the stable solid CO surrogate, which would not cause hydrodehalogenation of the starting materials. Remarkably, this method featured a very broad

  开发了 Pd 催化的 4 H -benzo[ d ][1,3]oxazin-4-one 衍生物的无 CO 羰基化合成。这种新方法使用容易获得的N -（邻溴芳基）酰胺作为起始原料，使用廉价的三甲酸苯-1,3,5-三酯（TFBen）作为稳定的固体 CO 替代物，不会引起起始原料的加氢脱卤。值得注意的是，该方法具有非常广泛的底物范围，特别适用于将苯并[ d ][1,3]oxazin-4-one结构引入药物和天然生物活性化合物中。
• Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
  作者：Subir Panja、Srabani Maity、Biju Majhi、Brindaban C. Ranu

  DOI：10.1002/ejoc.201900935

  日期：2019.9.8

  An efficient procedure for the Pd‐catalyzed olefination of 4H‐benzo[d][1,3]oxazin‐4‐ones with activated alkenes has been achieved via C‐H activation. The site selectivity of the reaction was explained by a DFT study.

  通过C-H活化，实现了有效的Pd催化4H-苯并[d] [1,3]恶嗪-4-烯与活化烯烃的烯化反应。DFT研究解释了反应的位点选择性。
• 1H and 13C NMR spectral studies of some 4H-3,1-benzoxazin-4-ones and their 2-acylaminobenzoic acid precursors
  作者：Alan G Osborne、Zia Goolamali

  DOI：10.1016/s1386-1425(99)00206-1

  日期：2000.5

  The 1H and 13C NMR spectra of twelve 4H-3,1-benzoxazine-4-ones and of their acylaminobenzoic acid precursors are presented. Differentiation between these two series of compounds is best achieved through the characteristic J(CH) coupling interactions in the high frequency carbonyl region. Some 4H-pyrido[2,3-d][1,3]oxazin-4-ones have also been studied and some earlier literature assignments revised.

  给出了十二个4H-3,1-苯并恶嗪-4-酮及其酰基氨基苯甲酸前体的1H和13C NMR光谱。这两个系列化合物之间的区别最好通过高频羰基区域中的特征性J（CH）偶联相互作用实现。还研究了一些4H-吡啶并[2,3-d] [1,3]恶嗪-4-酮，并对一些较早的文献进行了修订。
• Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents
  作者：Mujeeb Ur Rahman、Ankita Rathore、Anees A. Siddiqui、Gazala Parveen、M. Shahar Yar

  DOI：10.3109/14756366.2013.845820

  日期：2014.10.1

  To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. All the synthesized compounds were evaluated for their diuretic (by Lipschitz et al. method), antihypertensive activity by non-invasive blood pressure (NIBP) using the tail-cuff method and anti-diabetic potential in rats. Six compounds showing significantly excellent activity were compared with metolazone, prazosin and diazoxide as standards. Compound N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4 nitrobenzenesulfonamide (20) exhibited most potent of the series.