6-fluoro-2-(4-methoxyphenyl)benzoxazole | 1049032-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-fluoro-2-(4-methoxyphenyl)benzoxazole
• 英文别名: 2-(4-methoxyphenyl)-6-fluorobenzoxazole；6-Fluoro-2-(4-methoxyphenyl)-1,3-benzoxazole
• CAS: 1049032-87-2
• 化学式: C₁₄H₁₀FNO₂
• 分子量: 243.237
• InChiKey: WLBAMMQWOXLNLE-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：
  0.07
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-溴-4-氟苯基)-4-甲氧基苯甲酰胺 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 18.0h， 以77%的产率得到6-fluoro-2-(4-methoxyphenyl)benzoxazole
  参考文献：
  名称：

  强效抗肿瘤药2-（3,4-二甲氧基苯基）-5-氟苯并噻唑的苯并噻唑，苯并恶唑和chromen-4-one类似物的合成和生物学特性（PMX 610，NSC 721648）。

  摘要：

  已经合成了新的氟化的2-芳基-苯并噻唑，-苯并恶唑和-铬-4-酮，与有效的抗肿瘤苯并噻唑5相比，它们对MCF-7和MDA 468乳腺癌细胞系具有活性。 12a，d在两种细胞系中产生亚微摩尔GI 50值；然而，就抗肿瘤效力而言，新化合物均未达到5。对于5，似乎必须结合芳基烃受体，但不足以抑制生长。

  DOI：

  10.1021/jm800418z

文献信息

• Synthesis of benzoxazoles <i>via</i> an iron-catalyzed domino C–N/C–O cross-coupling reaction
  作者：Bo Yang、Weiye Hu、Songlin Zhang

  DOI：10.1039/c7ra13080e

  日期：——

  An eco-friendly and efficient method has been developed for the synthesis of 2-arylbenzoxazoles via a domino iron-catalyzed C–N/C–O cross-coupling reaction. Some of the issues typically encountered during the synthesis of 2-arylbenzoxazoles in the presence of palladium and copper catalysts, including poor substrate scope and long reaction times have been addressed using this newly developed iron-catalyzed

  开发了一种通过多米诺铁催化的 C-N/C-O 交叉偶联反应合成 2-芳基苯并恶唑的环保高效方法。使用这种新开发的铁催化方法已经解决了在钯和铜催化剂存在下合成 2-芳基苯并恶唑的过程中通常遇到的一些问题，包括底物范围差和反应时间长。
• Ligand-promoted, copper nanoparticles catalyzed one-pot synthesis of substituted benzoxazoles from 2-bromoanilines and acyl chlorides
  作者：Yong Wang、Chaolong Wu、Shoujie Nie、Dingjian Xu、Min Yu、Xiaoquan Yao

  DOI：10.1016/j.tetlet.2015.10.078

  日期：2015.12

  A facile, highly efficient, and practical one-pot synthetic strategy for benzoxazoles was developed by using copper nanoparticles as a catalyst with o-bromoanilines and acyl chlorides as starting materials. With the promotion of 1,10-phenanthroline ligand, the copper nanoparticles catalyst showed highly catalytic activity under mild conditions. This methodology is tolerant of a wide variety of functional groups and gives good to excellent yields in most examples. Furthermore, the solid catalyst could be recovered and reused conveniently several times with satisfactory yields. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Properties of Benzothiazole, Benzoxazole, and Chromen-4-one Analogues of the Potent Antitumor Agent 2-(3,4-Dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)
  作者：Stefania Aiello、Geoffrey Wells、Erica L. Stone、Hachemi Kadri、Rana Bazzi、David R. Bell、Malcolm F. G. Stevens、Charles S. Matthews、Tracey D. Bradshaw、Andrew D. Westwell

  DOI：10.1021/jm800418z

  日期：2008.8.1

  New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a, b and 12a, d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding

  已经合成了新的氟化的2-芳基-苯并噻唑，-苯并恶唑和-铬-4-酮，与有效的抗肿瘤苯并噻唑5相比，它们对MCF-7和MDA 468乳腺癌细胞系具有活性。 12a，d在两种细胞系中产生亚微摩尔GI 50值；然而，就抗肿瘤效力而言，新化合物均未达到5。对于5，似乎必须结合芳基烃受体，但不足以抑制生长。