4-Oxo-2,2,3-trimethyl-1,2,3,4-tetrahydro-chinazolin | 91718-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-Oxo-2,2,3-trimethyl-1,2,3,4-tetrahydro-chinazolin
• 英文别名: 2,2,3-Trimethyl-2,3-dihydroquinazolin-4(1H)-one；2,2,3-trimethyl-1H-quinazolin-4-one
• CAS: 91718-05-7
• 化学式: C₁₁H₁₄N₂O
• mdl: MFCD24391307
• 分子量: 190.245
• InChiKey: NQNSZSLGMDYNOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-azido-N-isopropyl-N-(isopropylcarbamoyl)benzamide 在 5,10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphyrin iron(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 30.0h， 以71%的产率得到4-Oxo-2,2,3-trimethyl-1,2,3,4-tetrahydro-chinazolin
  参考文献：
  名称：

  [Fe（F（20）TPP）Cl]催化分子内CN键的形成，以芳基叠氮化物为氮源进行生物碱合成。

  摘要：

  通过使用芳基叠氮化物作为氮源的[Fe（F（20）TPP）Cl]催化的分子内CN键形成，已成功完成了包括吲哚，二氢吲哚，四氢喹啉，二氢喹唑啉酮和喹唑啉酮在内的生物碱的合成。

  DOI：

  10.1039/c0cc01825b

文献信息

• Selective synthesis of functionalized quinazolinone derivatives via biocatalysis
  作者：Jin Lan、Zhanggao Le、Hongxia Li、Jia Meng、Bozhen Gong、Zongbo Xie

  DOI：10.1016/j.mcat.2020.111261

  日期：2020.12

  quinazolinone derivatives via tandem / hydrolysis / decarboxylation / cyclization and transesterification reactions has been developed that works with a variety of 2-aminobenzamide and β-dicarbonyl compounds. This method requires mild conditions, and has demonstrated high catalytic activity, excellent yields, excellent chemoselectivity, and a broad substrate scope. Additionally, biocatalyzed decarboxylation does

  通过串联/水解/脱羧/环化和酯交换反应构建功能化的喹唑啉酮衍生物的新型高效生物催化方法已经开发出来，可与多种2-氨基苯甲酰胺和β-二羰基化合物一起使用。该方法需要温和的条件，并显示出高催化活性，优异的收率，优异的化学选择性和广泛的底物范围。另外，生物催化的脱羧反应不需要高温或光活化，使其相对于替代技术具有实质优势。最重要的是，它为利用有机化学中的酶探索简单，便捷和环境友好的合成路线提供了新的实例。
• Copper-Catalyzed Reactions of Alkenyl Boronic Esters via Chan–Evans–Lam Coupling/Annulation Cascades: Substrate Selective Synthesis of Dihydroquinazolin-4-ones and Polysubstituted Quinolines
  作者：Yuge Li、Zifeng Cao、Zhijun Wang、Liang Xu、Yu Wei

  DOI：10.1021/acs.orglett.2c02522

  日期：2022.9.16

  nucleophiles have been established, providing new approaches for one-pot assembly of azacycles. Following the Chan–Evans–Lam C–N couplings, the cyclization processes occur via divergent pathways based on the utilized substrates, affording hydroamination product dihydroquinazolin-4-ones or aromatization product quinolines. Via this one-pot C–N coupling/annulation cascade, the target substituted azacycles can

  已经建立了铜催化的烯基硼酸酯和 N-H 基亲核试剂之间的级联环化反应，为氮杂环的一锅组装提供了新方法。在 Chan-Evans-Lam C-N 偶联之后，环化过程通过基于所用底物的不同途径发生，提供加氢胺化产物 dihydroquinazolin-4-ones 或芳构化产物喹啉。通过这种一锅 C-N 偶联/环化级联，可以在每种情况下以中等至良好的产率获得目标取代的氮杂环。
• 2,3-Dihydroquinazolin-4(1H)-ones: Visible light mediated synthesis, solvatochromism and biological activity
  作者：K. Hemalatha、G. Madhumitha、C.S. Vasavi、Punnagai Munusami

  DOI：10.1016/j.jphotobiol.2014.12.028

  日期：2015.2

  The photochemical synthesis of a series of 2,3-dihydroquinazolin-4(1H)-ones were evaluated under the irradiation of visible light (>390nm). The effect of the visible light mediated synthesis was carried out in the presence/absence of solvent. The effect of solvent plays a key role in the synthesis was evidenced through the formation of product in short duration. The solvatochromic effects of the fluorescent compounds (3a-k) were studied with respect to the solvents of increasing polarity (DCM<methanol<DMF<DMSO). The determination of in vitro anti-inflammatory activity of the compounds (3a-k) by the inhibition of bovine serum albumin (BSA) denaturation and 2,2-di(4-t-octylphenyl)-1-picrylhydrazyl (DOPPH) radical scavenging consequence of the compounds (3a-k) were determined by spectroscopic technique. The compound 3j in DMSO exhibited extreme high quantum yield. The compound 3i was found to be superior both in the efficiency of the anti-inflammatory activity and radical scavenging ability.
• Bhavani, A. K. D.; Reddy, P. S. N., Organic Preparations and Procedures International, 1992, vol. 24, # 1, p. 1 - 6
  作者：Bhavani, A. K. D.、Reddy, P. S. N.

  DOI：——

  日期：——
• [Fe(F20TPP)Cl] catalyzed intramolecular C–N bond formation for alkaloid synthesis using aryl azides as nitrogen source
  作者：Yungen Liu、Jinhu Wei、Chi-Ming Che

  DOI：10.1039/c0cc01825b

  日期：——

  tetrahydroquinolines, dihydroquinazolinones and quinazolinones have been accomplished in moderate to excellent yields via [Fe(F(20)TPP)Cl] catalyzed intramolecular C-N bond formation using aryl azides as nitrogen source.

  通过使用芳基叠氮化物作为氮源的[Fe（F（20）TPP）Cl]催化的分子内CN键形成，已成功完成了包括吲哚，二氢吲哚，四氢喹啉，二氢喹唑啉酮和喹唑啉酮在内的生物碱的合成。