3-phenyl-2-(trifluoromethyl)quinazolin-4(3H)-one

• 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: 3-phenyl-2-(trifluoromethyl)quinazolin-4(3H)-one
• 英文别名: 3-phenyl-2-(trifluoromethyl)quinazolin-4-one
• 化学式: C₁₅H₉F₃N₂O
• mdl: MFCD00714341
• 分子量: 290.244
• InChiKey: JRCSIJIHRYHSEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 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：
  32.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-碘苯胺 在 四氯化碳 、 1,3-双(二苯基膦)丙烷 、 sodium carbonate 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 生成 3-phenyl-2-(trifluoromethyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  由三氟乙酰亚胺基氯化物和硝基化合物催化钯催化羰基合成2-（三氟甲基）喹唑啉-4（3H）-酮

  摘要：

  已经完成了钯催化的三氟乙酰亚氨基氯化物和硝基化合物的羰基化反应，以构建药学上有价值的2-（三氟甲基）喹唑啉-4（3 H）-酮的方法。在该转化中，Mo（CO）6既用作方便的CO源，又用作还原剂。该新开发的方案可与各种硝基化合物兼容，并且可以轻松按比例放大至1 mmol规模。

  DOI：

  10.1002/adsc.202001502

文献信息

• FeCl₃-Mediated Synthesis of 2-(Trifluoromethyl)quinazolin-4(3<i>H</i>)-ones from Isatins and Trifluoroacetimidoyl Chlorides
  作者：Le-Cheng Wang、Shiying Du、Zhengkai Chen、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.0c01927

  日期：2020.7.17

  e annulation reaction for the efficient construction of 2-(trifluoromethyl)quinazolin-4(3H)-ones has been developed. This transformation employs readily available isatins and trifluoroacetimidoyl chlorides as the starting materials, providing a facile and practical route to diverse biologically relevant quinazolin-4(3H)-one derivatives. A plausible reaction pathway has been proposed based on the mechanistic

  已经开发出FeCl 3介导的级联偶合/脱羰环化反应，用于有效地构建2-（三氟甲基）喹唑啉-4（3 H）-one。该转化采用容易获得的靛红和三氟乙酰亚胺基氯作为起始原料，为各种生物学相关的喹唑啉-4（3H）-一衍生物提供了简便实用的途径。基于机理的观察已经提出了合理的反应途径。
• A Direct Method for Synthesis of Fluorinated Quinazolinones and Quinoxalines Using Fluorinated Acids without Metals or Additives
  作者：Chen Ma、Shichen Li、Xueyan Lv、Jianing Ren、Lei Feng

  DOI：10.1055/a-1824-6352

  日期：2022.9

  ketones, and heterocycles has been studied constantly in recent decades. Herein, a direct method using trifluoroacetic acid as a CF3 source for the synthesis of 2-(trifluoromethyl)quinazolin-4-ones and 4-(trifluoromethyl)pyrrolo/indolo[1,2-a]quinoxalines without any catalysts or additives is reported; a wide range of fluorinated compounds were obtained in 52%–94% yield.

  三氟甲基仅存在于合成化合物中。由于该组独特的生物活性，近几十年来一直在不断研究烷烃、芳烃、烯烃、醛和酮等不饱和化合物以及杂环的三氟甲基化。在此，使用三氟乙酸作为 CF 3源用于合成 2-(三氟甲基)喹唑啉-4-酮和 4-(三氟甲基)吡咯并/吲哚并[1,2- a ]喹喔啉的直接方法是，无需任何催化剂或添加剂。报告；以 52%–94% 的收率获得了范围广泛的含氟化合物。
• A Sustainable and Versatile Cellulose‐based CO Surrogate for Carbonylative Reactions
  作者：You Wang、Bing Tian、Yi Li、Wei Li、Zhijun Chen、Shouxin Liu、Shujun Li

  DOI：10.1002/cssc.202301324

  日期：——

  The highly toxic and flammable nature of CO lead to high handling demand for its use and storage, undoubtedly constricting its further academic exploration for carbonylative reactions in laboratory. Although many CO surrogates have been developed and applied in carbonylative reactions instead of CO gas, exploration of more versatile CO surrogates for diverse carbonylations is still highly desirable. Here we report a cellulose‐based CO surrogate (cellulose‐CO), which prepared from cheap and abundant cellulose through a simple and green process. The very mild and efficient CO release makes this reagent a highly competitive candidate for providing CO in carbonylation. This surrogate is compatible with a wide variety of functional groups in various carbonylative reactions due to the excellent compatibility of cellulose‐CO. Moreover, the cellulose‐CO exhibits excellent chemical stability which can be stored exposed to air for 12 months, making this CO surrogate a robust and general reagent in CO chemistry.

  摘要 CO 的高毒性和易燃性导致对其使用和储存的处理要求很高，这无疑限制了学术界对其在实验室羰基化反应中的进一步探索。尽管已经开发了许多 CO 代用品并将其应用于替代 CO 气体的羰基化反应中，但探索更多功能的 CO 代用品用于多种羰基化反应仍然是非常必要的。在此，我们报告了一种基于纤维素的 CO 代用品（纤维素-CO），它由廉价而丰富的纤维素通过简单的绿色工艺制备而成。这种试剂能非常温和、高效地释放 CO，是羰基化过程中提供 CO 的极具竞争力的候选试剂。由于纤维素-CO 具有出色的兼容性，这种代用试剂在各种羰基化反应中可与多种官能团兼容。此外，纤维素-CO 还具有极佳的化学稳定性，可暴露在空气中保存 12 个月，使这种 CO 代用试剂成为 CO 化学反应中一种坚固耐用的通用试剂。
• Etude du comportement de benzoxazinones, substituées en position 2 par des groupements (per)halogénés, vis-á-vis de l'aniline
  作者：B. Boutevin、L. Ranjalahy Rasoloarijao、A. Rousseau、J. Garapon、B. Sillion

  DOI：10.1016/s0022-1139(00)82790-6

  日期：1992.7

  This study describes firstly the synthesis of benzoxazinones substituted in position 2 by halogenated groups such as -(CH2)n-R(F, Cl) where n = 0, 1 and 2 and R(F, Cl) is a perhalogenated group, and secondly the reaction of these new benzoxazinones with aniline, in different media.Thus it is shown that the behaviour of trifluoromethyl-2-benzoxazinone towards aniline is different, in most cases, in comparison with benzoxazinones substituted by perfluorinated groups CnF2n+1 with n = 2, 3 and 7. Under certain conditions (hot ethanol and aniline with triphenyl phosphite), it is observed that nucleophilic attack of aniline only occurs on the carbonyl group when benzoxazinones are substituted by an electron-withdrawing group such as C2F5, C3F7 and C7F15.
• Identification of novel quinazolin-4(3H)-ones as inhibitors of thermolysin, the prototype of the M4 family of proteinases
  作者：Mahmud Tareq Hassan Khan、Rasool Khan、Yimingjiang Wuxiuer、Mohammad Arfan、Manzoor Ahmed、Ingebrigt Sylte

  DOI：10.1016/j.bmc.2010.04.083

  日期：2010.6.15

  A combinatorial series of novel quinazolin-4(3H)-ones were synthesised and their structures were established based on spectroscopic data (IR, NMR, EI-MS, and FAB-MS). The compounds were tested for inhibition of the zinc metalloproteinase thermolysin (TLN) utilizing a chemical array-based approach. Some of the compounds were found to inhibit TLN, with IC50 values ranging from 0.0115 mu M (compound 3) to 122,637 mu M (compound 29). Compound 3 [3-phenyl-2-(trifluoromethyl) quinazolin-4(3H)-one] (IC50 = 0.0115 mu M) and compound 35 [3-(isopropylideneamino)-2,2-dimethyl-2,3-dihydroquinazolin-4 (1H)-one] (IC50 = 0.2477 mu M) were found to be the most potent inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.