2-(2-甲氧基苯基)-3-苯基喹喔啉 | 10166-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-(2-甲氧基苯基)-3-苯基喹喔啉
• 英文名称: 2-(2-methoxyphenyl)-3-phenylquinoxaline
• 英文别名: 3-(2-Methoxyphenyl)-2-phenyl-chinoxalin
• CAS: 10166-77-5
• 化学式: C₂₁H₁₆N₂O
• 分子量: 312.371
• InChiKey: GRHHTAWTWPMOCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl (2-((1-(2-methoxyphenyl)-2-oxo-2-phenylethyl)amino)phenyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以85%的产率得到2-(2-甲氧基苯基)-3-苯基喹喔啉
  参考文献：
  名称：

  A novel route to synthesize libraries of quinoxalines via Petasis methodology in two synthetic operations

  摘要：

  This Letter reveals an innovative and facile procedure to prepare quinoxalines in two synthetic steps. The microwave assisted Petasis reaction is followed by the acid mediated unmasking of an internal amino nucleophile, cyclodehydration and oxidation to give collections of quinoxalines in good to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.115

文献信息

• Base-catalyzed multicomponent access to quinoxalin-2-thiones from <i>o</i>-phenylenediamines, aryl ketones and sulfur
  作者：Thanh Binh Nguyen、Dinh Hung Mac、Thi Minh Chau Tran、Bich Ngoc Nguyen、Hai Thuong Cao

  DOI：10.1039/d2ob01343f

  日期：——

  of acetophenones with o-phenylenediamines and sulfur in DMSO in the presence of piperidine as a catalyst. The products could be readily isolated from the reaction mixture by simple precipitation and washing with methanol. This set of reaction conditions applied to higher homologs of acetophenones as well as benzyl phenyl ketones led to 2,3-di-C-substituted quinoxalines. Further functionalization of

  3-Arylquinoxaline-2-thiones 是在哌啶作为催化剂存在下，通过苯乙酮与邻苯二胺和硫在 DMSO 中的三组分氧化缩合方便地合成的。通过简单的沉淀和用甲醇洗涤，可以容易地从反应混合物中分离出产物。应用于苯乙酮和苄基苯基酮的高级同系物的这组反应条件导致了 2,3-二-C-取代的喹喔啉。通过硫酮基团上的反应进一步官能化 3-苯基喹喔啉-2-硫酮可以很容易地以良好的收率提供喹喔啉衍生物。
• Efficient synthesis of quinoxalines with hypervalent iodine as a catalyst
  作者：Chung-Yu Chen、Wan-Ping Hu、Mei-Chun Liu、Pi-Cheng Yan、Jeh-Jeng Wang、Mei-Ing Chung

  DOI：10.1016/j.tet.2013.09.027

  日期：2013.11

  Various biologically important quinoxalines were efficiently synthesized in excellent yields via one-pot reaction between 1,2-diaminobenzenes and internal alkynes. The method utilizes inexpensive and readily available hypervalent iodine source, such as (diacetoxyiodo)benzene (PhI(OAc)(2)) and proved to be a better alternative as compared to expensive transition metal catalysts. Quinoxaline 4i [(2-phenyl-3-(3,4,5-trimethoxy phenyl)quinoxaline)] was evaluated for leukemia cancer cell lines and turned out to be a good candidate. (C) 2013 Elsevier Ltd. All rights reserved.
• A novel route to synthesize libraries of quinoxalines via Petasis methodology in two synthetic operations
  作者：Muhammad Ayaz、Justin Dietrich、Christopher Hulme

  DOI：10.1016/j.tetlet.2011.06.115

  日期：2011.9

  This Letter reveals an innovative and facile procedure to prepare quinoxalines in two synthetic steps. The microwave assisted Petasis reaction is followed by the acid mediated unmasking of an internal amino nucleophile, cyclodehydration and oxidation to give collections of quinoxalines in good to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.