2-ethyl-4-phenylquinazoline | 107288-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-ethyl-4-phenylquinazoline
• CAS: 107288-91-5
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: JNJCWIKIZXYGTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethyl-4-phenylquinazoline 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 N-[(1S,9S)-8,9-dimethyl-12-methylsulfonyl-1-phenyl-8,11,12-triazatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraen-10-yl]methanesulfonamide
  参考文献：
  名称：

  Ring Expansion of 2-Alkylidenedihydroquinazolines to Iminodihydro-1,4-benzodiazepines by Methanesulfonyl and Trifluoromethanesulfonyl Azide

  摘要：

  2-Alkyl-1 -methylquinazolinium hexafluorophosphates 9 are deprotonated by sodium or potassium hydride to afford solutions of 2-alkylidenedihydroquinazolines 10, which were investigated by NMR spectroscopy. Trapping with methanesulfonyl azide (5a) of 10 in situ or subsequent treatment with trifluoromethanesulfonyl azide (5b) gives mixtures of colourless (15) and intensely yellow N-sulfonylimino-1,4-benzodiazepines 16 along with products due to cleavage of the exocyclic double bond of 10, viz. 11 and 13. The ethylidene compound 10b yields the bicyclic products 18 and 19, apparently by complex sequences of reactions that are triggered by removal of the acidic proton at C-2 of 16b and 16f. The structures of the products are based on spectroscopic evidence and X-ray diffraction analyses performed on 15b, 16d, 16e, and 19.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1577::aid-ejoc1577>3.0.co;2-6
• 作为产物：
  描述：

  1-benzoyl-1,2-dihydro-4-phenylquinazoline-2-carbonitrile 在 氢氧化钾 、 sodium hydride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-ethyl-4-phenylquinazoline
  参考文献：
  名称：

  Uff, Barrie C.; Joshi, Bijaya L.; Popp, Frank D., Journal of the Chemical Society. Perkin transactions I, 1986, p. 2295 - 2304

  摘要：

  DOI：

文献信息

• Novel norepinephrine reuptake inhibitors for the treatment of central nervous system disorders
  申请人：Caprathe William Bradley

  公开号：US20050096327A1

  公开（公告）日：2005-05-05

  This invention relates to compounds of the formula 1 wherein R 1 , R 2 , and R 3 and R 4 are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

  这项发明涉及公式1的化合物 其中R 1 ，R 2 ，R 3 和R 4 如规范中所定义，包含它们的药物组合物以及它们在治疗中枢神经系统疾病中的用途。
• Preparation of 4-arylquinazolines with<i>o</i>-(<i>N</i>-alkyl,<i>N-p</i>-tosyl)aminobenzonitriles, aryllithiums, and NIS
  作者：Hiroki Naruto、Hideo Togo

  DOI：10.1039/d0ob01223h

  日期：——

  The treatment of o-(N-alkyl,N-p-tosyl)aminobenzonitriles with aryllithiums, followed by the reaction with water, NIS under irradiation with a fluorescent lamp, and then tBuOK gave 2-alkyl-4-arylquinazolines or 4-arylquinazolines in good to moderate yields. The present reaction proceeds through the formation of N-iodoimines from imines with NIS, the generation of iminyl radicals, the 1,6-H shift by

  治疗ø - （ñ -烷基，Np个甲苯磺酰基）与芳基锂aminobenzonitriles，随后与水的反应，NIS用荧光灯照射下，然后吨丁醇钾，得到2-烷基-4- arylquinazolines或4- arylquinazolines在良好至中等的产量。本反应通过与NIS的亚胺形成N-碘亚胺，亚胺基的产生，亚胺基的1,6-H转移，通过6 -exo-tet模式的环化以及最后消除p-来进行。甲苯磺酸盐生成2-烷基-4-芳基喹唑啉或4-芳基喹唑啉。
• Ru(II)-Catalyzed C–H Activation and Annulation Reaction via Carbon–Carbon Triple Bond Cleavage
  作者：Rashmi Prakash、Bidisha R. Bora、Romesh C. Boruah、Sanjib Gogoi

  DOI：10.1021/acs.orglett.8b00643

  日期：2018.4.20

  An unprecedented Ru(II)-catalyzed C–H activation and annulation reaction, which proceeds via C–C triple bond cleavage, is reported. This reaction of 2-phenyldihydrophthalazinediones with alkynes, which works most efficiently in the presence of bidented ligand 1,3-bis(diphenylphosphino)propane, affords good yields of substituted quinazolines.

  据报道，空前的Ru（II）催化的CH活化和环化反应是通过CC的三键裂解而进行的。2-苯基二氢酞嗪二酮与炔烃的这种反应在双键配体1,3-双（二苯基膦基）丙烷的存在下最有效地进行，产生了高产率的取代喹唑啉。
• An Efficient Three-component, One-pot Synthesis of Quinazolines under Solvent-free and Catalyst-free Condition
  作者：Subrahmanya Ishwar Bhat、U. K. Das、Darshak R. Trivedi

  DOI：10.1002/jhet.2220

  日期：2015.7

  protocol for the synthesis of quinazolines in the absence of solvent and catalyst has been developed. 2,4‐Disubstituted quinazolines have been synthesized from three‐component one‐pot reactions of 2‐aminoaryl ketones, orthoesters, and ammonium acetate. The present method has advantages of operational simplicity, substrate generality, clean reaction, high yields (76–94%), and moderate reaction time. The plausible

  已经开发出在没有溶剂和催化剂的情况下合成喹唑啉的有效绿色方案。由2-氨基芳基酮，原酸酯和乙酸铵的三组分一锅法反应合成了2,4-二取代的喹唑啉。本方法具有操作简单，底物通用，反应干净，收率高（76-94％）和反应时间适中的优点。基于分离的中间体的光谱表征和单晶X射线分析，提出了反应的合理机理。
• Visible light-induced one-pot three-component synthesis of quinazolines under catalyst-free condition
  作者：Xue Ma、Xuerou Chen、Letian Ying、Yuqi Pang、Qidi Zhong、Dongmei Li、Wuji Sun

  DOI：10.1016/j.mcat.2023.113276

  日期：2023.7

  A facile and efficient strategy for visible light-induced synthesis of quinazolines has been developed via one-pot three-component reaction of 2-aminoaryl ketones, aldehydes and ammonium acetate. This method displays high efficiency and broad substrate tolerance, allowing quick accesses to quinazolines under catalyst-free condition. The results reported herein disclose an important new application

  通过 2-氨基芳基酮、醛和乙酸铵的一锅三组分反应，开发了一种可见光诱导合成喹唑啉的简便有效的策略。该方法显示出高效率和广泛的底物耐受性，允许在无催化剂条件下快速获取喹唑啉。本文报道的结果公开了可见光诱导合成在有价值的有机产品的清洁合成中的重要新应用。