N-(4-phenoxyphenyl)benzo[d]oxazol-2-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-phenoxyphenyl)benzo[d]oxazol-2-amine
• 英文别名: N-(4-phenoxyphenyl)-1,3-benzoxazol-2-amine
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: DZPMYRHMEVVHJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-phenoxyphenyl)guanidine carbonate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.0h， 生成 N-(4-phenoxyphenyl)benzo[d]oxazol-2-amine
  参考文献：
  名称：

  通过胍环二亚胺活化在胍碳中心进行亲核取代

  摘要：

  尽管胍碳中心具有缺电子性质，但由于胍基团的共振稳定性，这些位点的亲核反应尚未发展。我们提出了一种胍 C-N 键取代策略，该策略需要形成胍环二亚胺 (GCDI) 结构，从而有效地破坏胍基团的共振结构。在酸添加剂的存在下，GCDIs 的胍碳中心与各种胺和醇发生亲核取代反应。

  DOI：

  10.1021/acs.orglett.1c03473

文献信息

• Synthesis of N-Aryl-2-aminobenzoxazoles from Substituted Benzoxazole-2-thiol and 2-Chloro-N-arylacetamides in KOH-DMF System
  作者：Guang-cheng Wang、Jing Wang、Lu-yao Li、Shan Chen、Ya-ping Peng、Zhen-zhen Xie、Ming Chen、Bing Deng、Wen-biao Li

  DOI：10.3987/com-17-13712

  日期：——

  A simple and novel method for the synthesis of N-aryl-2-aminobenzoxazoles from substituted benzoxazole-2-thiol and 2-chloro-N-arylacetamides in KOH-DMF system has been developed. The present protocol provides an attractive approach to access various N-aryl-2-aminobenzoxazoles in moderate to good yields without using transition metal catalyst under very mild reaction condition.
• Synthesis, biological evaluation and molecular docking study of N -arylbenzo[ d ]oxazol-2-amines as potential α-glucosidase inhibitors
  作者：Guangcheng Wang、Zhiyun Peng、Jing Wang、Juan Li、Xin Li

  DOI：10.1016/j.bmc.2016.08.061

  日期：2016.11

  A novel series of N-arylbenzo[d]oxazol-2-amines (4a-4m) were synthesized and evaluated for their alpha-glucosidase inhibitory activity. Compounds 4f-4i, 4k and 4m displayed potent inhibitory activity against alpha-glucosidase with IC50 values in the range of 32.49 +/- 0.17-120.24 +/- 0.51 mu M as compared to the standard drug acarbose. Among all tested compounds, compound 4g having 4-phenoxy substitution at the phenyl ring was found to be the most active inhibitor of ot-glucosidase with an IC50 value of 32.49 +/- 0.17 mu M. Analysis of the kinetics of enzyme inhibition indicated that compound 4g is a noncompetitive inhibitor of alpha-glucosidase with a K-i value of 31.33 mu M. Binding interaction of compound 4g with alpha-glucosidase was explored by molecular docking simulation. (C) 2016 Elsevier Ltd. All rights reserved.
• Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation
  作者：Taeyang An、Yan Lee

  DOI：10.1021/acs.orglett.1c03473

  日期：2021.12.3

  of the guanidine carbon centers, nucleophilic reactions at these sites have been underdeveloped because of the resonance stabilization of the guanidine group. We propose a guanidine C–N bond substitution strategy entailing the formation of guanidine cyclic diimide (GCDI) structures, which effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine

  尽管胍碳中心具有缺电子性质，但由于胍基团的共振稳定性，这些位点的亲核反应尚未发展。我们提出了一种胍 C-N 键取代策略，该策略需要形成胍环二亚胺 (GCDI) 结构，从而有效地破坏胍基团的共振结构。在酸添加剂的存在下，GCDIs 的胍碳中心与各种胺和醇发生亲核取代反应。