7-methoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one | 13234-81-6

• 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-methoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 7-Methoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one；7-methoxy-2-methyl-3,1-benzoxazin-4-one
• CAS: 13234-81-6
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: CHSPGGODZXJFHS-UHFFFAOYSA-N

物化性质

• 熔点：
  127 °C
• 沸点：
  341.9±44.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one 生成 N-(2-benzoyl-5-methoxy-phenyl)-phthalimide
  参考文献：
  名称：

  558.一些2-氨基-和2-邻苯二甲酰亚胺基-二苯甲酮的制备

  摘要：

  DOI：

  10.1039/jr9590002779
• 作为产物：
  描述：

  间苯胺氢氟乙酰氯 在 sodium hydroxide 、 双氧水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.67h， 生成 7-methoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  Synthesis and Characterization of 3-Arylquinazolinone and 3-Arylquinazolinethione Derivatives as Selective Estrogen Receptor Beta Modulators

  摘要：

  On the basis of the stucture of genistein, a new series of 3-arylquinazolines was prepared and tested for their estrogen receptor (ER) alpha and beta affinities. 5,7-Dihydroxy-3 -(4-hydroxyphenyl)-4(3H)-quinazolinone (1aa) acts as an agonist on both ER subtypes. It has 62-fold higher binding affinity [IC50(ER beta) = 179 nM] and 38-fold higher functional potency in a transcription assay [EC50(ER beta) = 76 nM] with ER beta than with ER alpha, thus improving upon the selectivity of genistein. All of the analogues showed preferential binding affinity for ER. Many are also more potent in activating transcription by ER beta than by ER alpha. Transformation of the C=O functionality at position 4 into a C=S group provided 5,7-dihydroxy-3-(4-hydroxyphenyl)4(3H)-quinazolinethione (1ba), which acts as an agonist on both ER subtypes but has 56-fold higher binding affinity for ER beta over ER alpha [IC50(ER beta) = 47 nM] and 215-fold higher potency in the transcription assay [EC50(ER beta) = 13 nM]. These ER beta-selective compounds may represent valuable tools in understanding the differences in structure and biological function of ER beta and ER alpha.

  DOI：

  10.1021/jm0509389

文献信息

• Recyclable palladium-catalyzed carbonylative annulation of 2-iodoanilines with acid anhydrides: A practical synthesis of 2-alkylbenzoxazinones
  作者：Zebiao Zhou、Bin Huang、Mingzhong Cai

  DOI：10.1080/00397911.2021.1966039

  日期：2021.10.18

  highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-iodoanilines and acid anhydrides has been developed. The reaction proceeds effectively in toluene using N,N-diisopropylethylamine (DiPEA) as the base at 100 °C under 2 bar of CO and provides a novel, general, and practical method for the assembly of a wide variety of 2-alkylbenzoxazinones with high functional group tolerance

  摘要 已经开发了一种高效的多相钯催化的 2-碘苯胺和酸酐的羰基化环化。该反应在甲苯中使用N,N-二异丙基乙胺 (DiPEA) 作为碱在 100 °C 和 2 bar CO 下有效进行，为组装各种具有高官能团耐受性和良好的收率。这种负载的钯配合物可以很容易地从产物中分离出来，并通过反应溶液的简单过滤进行回收，并以几乎一致的催化效率重复使用多达七次。
• 4H-Benzo[d][1,3]oxazin-4-ones and Dihydro Analogs from Substituted Anthranilic Acids and Orthoesters
  作者：Joel K. Annor-Gyamfi、Richard A. Bunce

  DOI：10.3390/molecules24193555

  日期：——

  (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.

  已开发出一种制备 2-烷基和 2-芳基-4H-苯并[d][1,3]恶嗪-4-酮（也称为 4H-3,1-苯并恶嗪-4-酮）的一锅法，并学习了。该方法包括芳基取代的邻氨基苯甲酸与原酸酯在乙醇中的乙酸催化反应。此外，我们还研究了微波条件下的反应。并非所有底物都能成功产生目标杂环，因为一些反应未能进行最终消除。该过程导致 (±)-2-烷基/芳基-2-乙氧基-1,2-二氢-4H-苯并[d][1,3]恶嗪-4-酮的分离。二氢类似物的形成与芳环上的电子密度相关：给电子基团有利于 4H-苯并[d][1,3]恶嗪-4-酮，而吸电子基团有利于二氢产物.
• Synthesis and Evaluation of Structurally Constrained Quinazolinone Derivatives as Potent and Selective Histamine H₃ Receptor Inverse Agonists
  作者：Tsuyoshi Nagase、Takashi Mizutani、Etsuko Sekino、Shiho Ishikawa、Sayaka Ito、Yuko Mitobe、Yasuhisa Miyamoto、Ryo Yoshimoto、Takeshi Tanaka、Akane Ishihara、Norihiro Takenaga、Shigeru Tokita、Nagaaki Sato

  DOI：10.1021/jm800569w

  日期：2008.11.13

  A series of structurally constrained derivatives of the potent H 3 inverse agonist 1 was designed, synthesized, and evaluated as histamine H 3 receptor inverse agonists. As a result, the N-cyclobutylpiperidin-4-yloxy group as in 2f was identified as an optimal surrogate structure for the flexible 1-pyrrolidinopropoxy group of 1. Subsequent optimization of the quinazolinone core of 2f revealed that

  设计，合成并评价了一系列有效的H 3反向激动剂1的结构受约束的衍生物，并将其评估为组胺H 3受体反向激动剂。结果，如2f中的N-环丁基哌啶-4-基氧基被鉴定为1的柔性1-吡咯烷基丙氧基的最佳替代结构。随后对2f的喹唑啉酮核心的优化表明，在2f的5-位取代。喹唑啉酮环影响效能。代表性衍生物5a和5s在大鼠的组胺释放测定和小鼠的受体占用测定中显示出增强的效力。
• Design, Synthesis, Antibacterial Evaluation, Three-Dimensional Quantitative Structure–Activity Relationship, and Mechanism of Novel Quinazolinone Derivatives
  作者：Lihui Shao、Su Zhao、Song Yang、Xiang Zhou、Yan Li、Chengpeng Li、Danping Chen、Zhuirui Li、Guiping Ouyang、Zhenchao Wang

  DOI：10.1021/acs.jafc.2c07264

  日期：2023.3.8

  Plant bacterial illnesses are common and cause dramatic damage to agricultural goods all over the world, yet there are few efficient bactericides to alleviate them at present. To discover novel antibacterial agents, two series of quinazolinone derivatives with novel structures were synthesized and their bioactivity against plant bacteria was tested. Combining CoMFA model search and the antibacterial

  植物细菌性病害很常见，对全世界的农产品造成巨大损害，但目前几乎没有有效的杀菌剂来缓解这些病害。为发现新型抗菌剂，合成了两个系列的具有新型结构的喹唑啉酮衍生物，并测试了它们对植物细菌的生物活性。结合 CoMFA 模型搜索和抗菌生物活性测定，D32被确定为一种有效的抗米黄单胞菌pv抗菌抑制剂。Oryzae ( Xoo ) 的 EC 50值为 1.5 μg/mL，与双噻唑 (BT) 和硫代二唑铜 (TC)（31.9 和 74.2 μg/mL）相比，抑制能力要好得多。化合物D32的活性体内对水稻细菌性叶枯病的抑制作用分别为46.7%（保护活性）和43.9%（治疗活性），优于市售药物噻二唑铜（29.3%的保护活性和30.6%的治疗活性）。流式细胞术、蛋白质组学、活性氧和关键防御酶被用于进一步研究D32的相关作用机制。D32作为抗菌抑制剂的鉴定及其识别机制的揭示不仅为开发治疗Xoo的新治疗策略提供了可
• Sulfone polymer composition
  申请人：SOLVAY SPECIALTY POLYMERS USA, LLC

  公开号：US11352499B2

  公开（公告）日：2022-06-07

  The invention pertains to a polymer composition possessing improved resistance towards degradation and discolouring phenomena induced by UV radiation, said composition comprising at least one aromatic sulfone polymer; at least one organic UV absorber and at least one basic compound selected from the group consisting of (i) basic oxides and hydroxides of divalent metals and (ii) salts of a weak acid, and to methods for its manufacture and to shaped articles obtained therefrom.

  本发明涉及一种聚合物组合物，该组合物具有更好的抗紫外线辐射引起的降解和褪色现象的能力，所述组合物包括至少一种芳香族砜聚合物；至少一种有机紫外线吸收剂和至少一种碱性化合物，所述碱性化合物选自(i)二价金属的碱性氧化物和氢氧化物和(ii)弱酸盐组成的组，本发明还涉及其制造方法和由此获得的成型物品。