2-(1H-1,2,3-benzotriazol-1-yl)-1,2-diphenylethanone | 147861-19-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(1H-1,2,3-benzotriazol-1-yl)-1,2-diphenylethanone
• 英文别名: 2-(1H-1,2,3-Benzotriazol-1-yl)-1,2-diphenylethan-1-one；2-(benzotriazol-1-yl)-1,2-diphenylethanone
• CAS: 147861-19-6
• 化学式: C₂₀H₁₅N₃O
• 分子量: 313.359
• InChiKey: DVVYSUCBMDZKKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-1,2,3-benzotriazol-1-yl)-1,2-diphenylethanone 在 formamide 作用下， 反应 6.0h， 以50%的产率得到2,4-二苯基喹唑啉
  参考文献：
  名称：

  Ring-Opening Rearrangements of 2-(Benzotriazol-1-yl) Enamines and a Novel Synthesis of 2,4-Diarylquinazoline

  摘要：

  2-(Benzotriazol-1-yl) enamines (readily available from lithiated 1-(arylmethyl) benzotriazole and nitriles) undergo facile rearrangement into 2,4-diarylquinazolines. A plausible mechanism for this novel rearrangement is proposed and supported.

  DOI：

  10.1021/jo00106a041
• 作为产物：
  描述：

  苯甲酸甲酯 、 1-苄基-1H-苯并三唑 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.0h， 以98%的产率得到2-(1H-1,2,3-benzotriazol-1-yl)-1,2-diphenylethanone
  参考文献：
  名称：

  A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles

  摘要：

  Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave alpha-(benzotriazol-1-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, alpha-(benzotriazol-1-yl) ketones 22 can be accessed by the reaction of alpha-(benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl)hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of hydrazones 5, 21, and 28 with n-butyllithium in diethyl ether resulted in the elimination of the tosyl group, dinitrogen, and benzotriazolyl group to afford the corresponding acetylenes 9, 23, and 29 in good yields. When alpha-(benzotriazol-1-yl) 1-alpha-phenoxy hydrazones 14 were treated with methyllithium, n-butyllithium, or phenyllithium, alkynes 18 were obtained, in which phenoxy groups were replaced by the lithium reagents.

  DOI：

  10.1021/jo962291t

文献信息

• Design, Synthesis and Antifungal Activity of Some New Imidazole and Triazole Derivatives
  作者：Zahra Rezaei、Soghra Khabnadideh、Kamiar Zomorodian、Kyvan Pakshir、Giti Kashi、Narges Sanagoei、Sanaz Gholami

  DOI：10.1002/ardp.201000357

  日期：2011.10

  Triazole and imidazole are incorporated into the structures of many antifungal compounds. In this study a novel series of 1,2,4‐triazole, imidazole, benzoimidazole, and benzotriazole derivatives was designed as inhibitors of cytochrome P450 14α‐demethylase (14DM). These structures were docked into the active site of MT‐CYP51, using Autodock program. Sixteen compounds with the best binding energy were

  三唑和咪唑被结合到许多抗真菌化合物的结构中。在这项研究中，设计了一系列新的 1,2,4-三唑、咪唑、苯并咪唑和苯并三唑衍生物作为细胞色素 P450 14α-脱甲基酶 (14DM) 的抑制剂。使用 Autodock 程序将这些结构对接到 MT-CYP51 的活性位点。合成了具有最佳结合能的 16 种化合物。新化合物的化学结构通过元素和光谱（1H-NMR 和质谱）分析得到证实。研究了所有化合物对白色念珠菌、热带念珠菌、光滑念珠菌、近皮念珠菌、克鲁泽念珠菌、都柏林念珠菌、烟曲霉、黄曲霉、犬小孢子菌、石膏小孢子菌、毛癣菌属植物的抗真菌活性。一些化合物对大多数测试的真菌显示出优异的体外抗真菌活性。化合物 2、9 和 10 对几种对氟康唑和伊曲康唑的耐药真菌具有抗真菌活性。
• FACILE PREPARATION OF 4-SUBSTITUTED QUINAZOLINES AND RELATED HETEROCYCLES
  申请人：Wang Zerong Daniel

  公开号：US20120283436A1

  公开（公告）日：2012-11-08

  A straightforward single step method for the preparation and/or production of substituted quinazolines is disclosed, wherein said quinazolines preferably contain one substituent at position 4, and may contain other functional groups at various positions, such as 5, 6, 7, and/or 8 of quinazolines. In addition, the extension of this new method leads to the formation of different type of heterocyclic aromatic compounds, that include but are not limited to perimidines, anthrapyrimidin-7-ones (also known as anthrapyrimidinones), anthra[1,9:5,10]dipyrimidines (also known as quinazoline[5,4-ef]perimidines) and benzo[e]-pyrimido[4,5,6-gh]pyrimidines.

  本发明揭示了一种制备和/或生产取代喹唑啉的简单单步方法，其中所述喹唑啉优选在位置4处含有一个取代基，并且可能在喹唑啉的各种位置，例如5、6、7和/或8处含有其他官能团。此外，这种新方法的扩展还导致不同类型的杂环芳香化合物的形成，包括但不限于咪唑啉、蒽吡咯啉-7-酮（也称为蒽吡咯啉酮）、蒽[1,9:5,10]二咪唑啉（也称为喹唑啉[5,4-ef]咪唑啉）和苯并[e]-嘧啶[4,5,6-gh]嘧啶。
• Facile preparation of 4-substituted quinazolines and related heterocycles
  申请人：Wang Zerong Daniel

  公开号：US09273012B2

  公开（公告）日：2016-03-01

  A straightforward single step method for the preparation and/or production of substituted quinazolines is disclosed, wherein said quinazolines preferably contain one substituent at position 4, and may contain other functional groups at various positions, such as 5, 6, 7, and/or 8 of quinazolines. In addition, the extension of this new method leads to the formation of different type of heterocyclic aromatic compounds, that include but are not limited to perimidines, anthrapyrimidin-7-ones (also known as anthrapyrimidinones), anthra[1,9:5,10]dipyrimidines (also known as quinazoline[5,4-ef]perimidines) and benzo[e]-pyrimido[4,5,6-gh]pyrimidines.

  本发明揭示了一种制备和/或生产取代喹唑啉的简单单步方法，其中所述喹唑啉优选在4号位置含有一种取代基，并且可能在喹唑啉的5、6、7和/或8号位置含有其他官能团。此外，这种新方法的扩展可以导致形成不同类型的杂环芳香化合物，包括但不限于咪唑啉、蒽并咪唑啉-7-酮（也称为蒽并咪唑酮）、蒽[1,9:5,10]二咪唑啉（也称为喹唑啉[5,4-ef]咪唑啉）和苯并[e]-咪唑并[4,5,6-gh]咪唑啉。
• Katritzky, Alan R.; Wu, Jing; Wrobel, Leszek, Acta Chemica Scandinavica, 1993, vol. 47, # 2, p. 167 - 175
  作者：Katritzky, Alan R.、Wu, Jing、Wrobel, Leszek、Rachwal, Stanislaw、Steel, Peter J.

  DOI：——

  日期：——
• Katritzky, Alan R.; Wang, Junquan; Henderson, Scott A., Heterocycles, 1998, vol. 48, # 8, p. 1567 - 1574
  作者：Katritzky, Alan R.、Wang, Junquan、Henderson, Scott A.

  DOI：——

  日期：——