2-(3-溴苯基)-4H-3,1-苯并恶嗪-4-酮 | 53463-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 2-(3-溴苯基)-4H-3,1-苯并恶嗪-4-酮
• 英文名称: 2-(3-bromophenyl)-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 2-(3-Bromo-phenyl)-4H-3,1-benzoxazin-4-one；2-(3-bromophenyl)-4H-3,1-benzoxazin-4-one；2-(3-bromophenyl)-3,1-benzoxazin-4-one
• CAS: 53463-67-5
• 化学式: C₁₄H₈BrNO₂
• 分子量: 302.127
• InChiKey: PLJJOOVEIBZBDF-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  399.4±21.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(3-溴苯基)-4H-3,1-苯并恶嗪-4-酮 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成
  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：

  3-溴苯甲酰氯 在 silver hexafluoroantimonate 、 carbonyl(η-5-cyclopentadienyl)diiodocobalt(III) 、 盐酸羟胺 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 2-(3-溴苯基)-4H-3,1-苯并恶嗪-4-酮
  参考文献：
  名称：

  通过Cp * Co（III）催化的C–H活化直接合成苯并恶嗪酮，并与二恶唑酮环化磺化ox盐。

  摘要：

  通过Cp * Co（III）催化的C–H活化和sulf代氧鎓叶立德与二恶唑酮之间的[3 + 3]环化反应，开发了苯并恶嗪酮的高度新颖和直接的合成方法。该反应在无碱条件下进行，并能耐受各种官能团。从各种容易获得的亚砜基砜和二恶唑酮开始，可以一步合成32％-75％收率的各种苯并恶嗪酮。

  DOI：

  10.1016/j.cclet.2020.09.020

文献信息

• Ruthenium catalyzed chemo and site-selective C–H amidation of oxobenzoxazine derivatives with sulfonyl azides
  作者：Manickam Bakthadoss、Polu Vijay Kumar、Ravan Kumar、Manickam Surendar、Duddu S. Sharada

  DOI：10.1039/c9nj02452b

  日期：——

  A novel and general protocol towards the synthesis of highly functionalized ortho-amido oxobenzoxazine frameworks via ruthenium catalyzed intermolecular C–H amidation using sulfonyl azides as amidation components has been developed for the first time.

  通过钌催化的分子间C-H胺化，使用磺酰叠氮化合物作为胺化组分，首次开发了合成高度官能化的邻胺基氧代苯并噁嗪骨架的新颖通用协议。
• TBHP/CoCl₂-Mediated Intramolec­ular Oxidative Cyclization of<i>N</i>-(2-Formylphenyl)amides: An Approach to the Construction of 4<i>H</i>-3,1-Benz­oxazin-4-ones
  作者：Junchao Yu、Daisy Zhang-Negrerie、Yunfei Du

  DOI：10.1002/ejoc.201501359

  日期：2016.1

  The intramolecular oxidative cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)–O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as an oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives and features readily available

  N-(2-甲酰基苯基)酰胺的分子内氧化环化是通过醛碳和酰胺氧之间的氧化C(sp2)-O(sp2)键形成反应实现的。这种使用叔丁基过氧化氢 (TBHP) 作为氧化剂和 CoCl2 作为催化剂的新策略允许有效地共催化合成有用的苯并恶嗪-4-one 衍生物，并具有易于获得的起始材料和温和的反应条件。
• 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。
• Palladium catalyzed chemo- and site-selective C–H acetoxylation and hydroxylation of oxobenzoxazine derivatives
  作者：Manickam Bakthadoss、Polu Vijay Kumar、Ravan Kumar、Vishal Agarwal

  DOI：10.1039/c9ob00642g

  日期：——

  An efficient protocol for the introduction of acetoxy and hydroxy functionalities on unactivated aryl sp2 carbons of oxobenzoxazine derivatives via an ortho-C–H activation reaction using a palladium catalyst has been developed for the first time. Interestingly, this intermolecular C–H functionalization reaction takes place in a facile and simple manner with high chemo- and site selectivity.

  用于引入上未活化的芳基SP乙酰氧基和羟基官能团的有效协议2个碳oxobenzoxazine衍生物经由一个邻使用钯催化剂-C-H活化反应已发展为第一次。有趣的是，这种分子间CH官能化反应以简便，简单的方式进行，具有很高的化学和位点选择性。
• Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of a-Chymotrypsin Inhibitors
  作者：Zulfiqar Ali Khan、Noshaba Afzal、Zaib Hussain、Syed Ali Raza Naqvi、Ayesha Bari、Sohail Anjum Shahzad、Muhammad Yar、Nasir Mahmood、Shazia Anwer Bukhari、Asim Mansha、Ameer Fawad Zahoor、Abdur Rahman Khan、Matloob Ahmad

  DOI：10.14233/ajchem.2014.16108

  日期：——

  Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structure-activity relationship were tested against a-chymotrypsin. Majority of synthesized compounds showed significant in vitro a-chymotrypsin inhibitory properties having IC50 values in the range of 5.42 ± 1.66 – 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1-benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3,1-benzoxazin-4-one (3t) with IC50 values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.

  合成了21种2-芳基-4H-3,1-苯并噁嗪-4-酮的衍生物，并测试了它们的潜在治疗意义和结构-活性关系对抗α-胰蛋白酶。大多数合成化合物显示出显著的体外α-胰蛋白酶抑制特性，IC50值范围为5.42 ± 1.66 – 41.27 ± 1.33 μM，而标准抑制剂chymostatin的IC50值为7.13 ± 1.06 μM。在本系列中，2-(2-氟苯基)-4H-3,1-苯并噁嗪-4-酮（3h）、2-(2-溴苯基)-4H-3,1-苯并噁嗪-4-酮（3n）和2-(1-萘基)-4H-3,1-苯并噁嗪-4-酮（3t）的IC50值分别为7.22 ± 0.75、6.99 ± 0.29和5.42 ± 1.66 μM，被发现是系列中最活跃的化合物，甚至优于标准抑制剂α-胰蛋白酶抑制剂chymostatin。