2-ethyl-3-p-tolylquinazolin-4(3H)-one | 50498-61-8

• 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: 2-ethyl-3-p-tolylquinazolin-4(3H)-one
• 英文别名: 2-ethyl-3-(4-tolyl)quinazolin-4(3H)-one；2-ethyl-3-(4-methylphenyl)quinazolin-4(3H)-one；2-Ethyl-3-p-tolyl-4-chinazolon；2-ethyl-3-p-tolyl-3H-quinazolin-4-one；2-Aethyl-3-p-tolyl-3H-chinazolin-4-on；4(3H)-Quinazolinone, 2-ethyl-3-(4-methylphenyl)-；2-ethyl-3-(4-methylphenyl)quinazolin-4-one
• CAS: 50498-61-8
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: NIBWCLOUGWNPPP-UHFFFAOYSA-N

物化性质

• 熔点：
  162-164 °C(Solv: ethanol (64-17-5))
• 沸点：
  435.8±38.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethyl-3-p-tolylquinazolin-4(3H)-one 在 溴 、 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 N-[2-(dimethylamino)ethyl]-N-[1-[3-(4-methylphenyl)-4-oxoquinazolin-2-yl]ethyl]decanamide
  参考文献：
  名称：

  Synthesis and structure–activity relationship of 3-phenyl-3H-quinazolin-4-one derivatives as CXCR3 chemokine receptor antagonists

  摘要：

  A series of 3-phenyl-3H-quinazolin-4-ones have been synthesized and tested for affinity and activity at the chemokine CXCR3 receptor. The most potent compound (1d) has been evaluated using radioligand binding and calcium mobilization assays and is considered a useful tool for further characterization of the CXCR3 receptor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.070
• 作为产物：
  描述：

  2-氨基-N-对甲苯苯甲酰胺 在 碘 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 2-ethyl-3-p-tolylquinazolin-4(3H)-one
  参考文献：
  名称：

  Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones

  摘要：

  A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (-)-circumdatin-F and (-)-fumiquinazoline-F. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.032

文献信息

• Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation
  作者：Jin-Bao Peng、Hui-Qing Geng、Wei Wang、Xinxin Qi、Jun Ying、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2018.06.007

  日期：2018.9

  A palladium-catalyzed four-component carbonylative cyclization reaction for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones has been developed. A range of different 2,3-disubstituted quinazolin-4(3H)-one derivatives were prepared in moderate to good yields employing simple and readily accessible 2-iodoanilines, nitro compounds and acid anhydrides as the synthetic precursors. Mo(CO)6 acted

  已经开发了钯催化的四组分羰基环化反应，用于合成2,3-二取代的喹唑啉-4（3H）-one。使用简单且易于获得的2-碘苯胺，硝基化合物和酸酐作为合成前体，以中等至良好的产率制备了一系列不同的2,3-二取代的喹唑啉-4（3H）-one衍生物。Mo（CO）6既充当固体CO源又充当还原剂。值得注意的是，在我们的条件下，甲喹酮作为镇静剂和催眠药也可以很容易地制备，收率为68％（4b）。
• One‐Pot Synthesis of Mono‐ and Disubstituted (3<i>H</i>)‐Quinazolin‐4‐ones in Dry Media Under Microwave Irradiation
  作者：Minoo Dabiri、Peyman Salehi、Ali A. Mohammadi、Mostafa Baghbanzadeh

  DOI：10.1081/scc-200048462

  日期：2005.1

  supported on silica gel is an efficient medium for one‐pot synthesis of (3H)‐quinazolin‐4‐ones in the absence of solvent under microwave irradiation or classical heating. The reaction of orthoesters with 2‐aminobenzamides ends up with the formation of monosubstituted (3H)‐quinazolin‐4‐ones. One‐pot synthesis of disubstituted (3H)‐quinazolin‐4‐ones is also achieved by the reaction of isatoic anhydride

  摘要 硅胶负载的 AlCl3/ZnCl2 混合物是一种有效的介质，可在微波辐射或经典加热下，在无溶剂的情况下，一锅法合成 (3H)-喹唑啉-4-酮。原酸酯与 2-氨基苯甲酰胺的反应最终形成单取代的 (3H)-喹唑啉-4-酮。二取代（3H）-喹唑啉-4-酮的一锅合成也可以通过靛红酸酐与伯胺和原酸酯的反应来实现。
• Functionalized Carbodiimide Mediated Synthesis of 2,3-Disubstituted Quinazolin-4(3H)-ones via the Tandem Strategy of C-Nucleophilic Addition and Intramolecular NH-Substitution Cyclization
  作者：Takao Saito、Hayato Nakano、Noriki Kutsumura

  DOI：10.1055/s-0032-1316773

  日期：——

  moiety at the proximal ester group. A facile synthesis of quinazolin-4(3H)-ones possessing carbon substituents at positions 2 and 3 has been developed. Key to the synthesis is a tandem strategy involving introduction of a 2-substituent and construction of the quinazolinone framework via C-nucleophilic addition to the carbodiimide cumulenic carbon followed by intramolecular nucleophilic substitution by

  摘要 已经开发了一种容易合成的在位置2和3具有碳取代基的喹唑啉4（3 H）-的方法。合成的关键是串联策略，包括引入2-取代基并通过C-亲核加成到碳二亚胺积碳中，然后通过近端酯基上新形成的NH部分进行分子内亲核取代，来构建喹唑啉酮骨架。 已经开发了一种容易合成的在位置2和3具有碳取代基的喹唑啉4（3 H）-的方法。合成的关键是串联策略，包括引入2-取代基并通过C-亲核加成到碳二亚胺积碳中，然后通过近端酯基上新形成的NH部分进行分子内亲核取代，来构建喹唑啉酮骨架。
• Catalytic Enantioselective Synthesis of N–C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization
  作者：Motohiro Hirai、Shumpei Terada、Hiroaki Yoshida、Kenki Ebine、Tomoaki Hirata、Osamu Kitagawa

  DOI：10.1021/acs.orglett.6b02865

  日期：2016.11.4

  In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH4 gave optically active N–C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmetric desymmetrization (enantioselective monohydrodebromination) followed by kinetic resolution of the resulting monobromophenyl products (up to 99% ee). The enantioselectivity

  在（R）-DTBM-SEGPHOS-Pd（OAc）2催化剂的存在下，用NaBH 4处理各种3-（2,6-二溴苯基）喹唑啉-4-酮可得到旋光的N-C轴向手性喹唑啉酮（甲喹酮） ）衍生物通过还原性不对称脱对称化（对映选择性单氢脱溴化作用），然后动力学拆分所生成的单溴代苯基产物（ee高达99％）。对映选择性在很大程度上取决于C4'位置的取代基（R 2），NaBH 4的量和反应温度。
• Nafion-H: An Efficient and Recyclable Heterogeneous Catalyst for the One-Pot Synthesis of 2,3-Disubstituted 4-(3<i>H</i>)-Quinazolinones under Solvent-Free Microwave Irradiation Conditions
  作者：P. Rao、B. Lingaiah、G. Ezikiel、T. Yakaiah、G. Reddy

  DOI：10.1055/s-2006-950428

  日期：2006.9

  A one-pot synthesis of 2,3-disubstituted 4-(3H)-quinazolinones has been carried out efficiently by the three-component coupling of isatoic anhydride/anthranilic acid, orthoesters, and amines in the presence of Nafion-H (a perfluorinated resin-supported sulfonic acid) as a heterogeneous catalyst. The reaction occurred within a few minutes under solvent-free microwave irradiation conditions to afford

  2,3-二取代 4-(3H)-喹唑啉酮的一锅合成已通过在 Nafion-H（一种全氟化树脂负载的磺酸）作为多相催化剂。在无溶剂微波辐射条件下，反应在几分钟内发生，以良好的收率得到产物。回收并循环使用催化剂。