(5-bromobenzo[d]oxazol-2-yl)(phenyl)methanone | 1638125-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-bromobenzo[d]oxazol-2-yl)(phenyl)methanone
• 英文别名: 2-Benzoyl-5-bromo-1,3-benzoxazole；(5-bromo-1,3-benzoxazol-2-yl)-phenylmethanone
• CAS: 1638125-49-1
• 化学式: C₁₄H₈BrNO₂
• 分子量: 302.127
• InChiKey: SHBRELGKYOVMMX-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  427.2±37.0 °C(Predicted)
• 密度：
  1.558±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙炔 在 N-溴代丁二酰亚胺(NBS) 、 二乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (5-bromobenzo[d]oxazol-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Synthesis of 2-Keto(hetero)aryl Benzox(thio)azoles through Base Promoted Cyclization of 2-Amino(thio)phenols with α,α-Dihaloketones

  摘要：

  An interesting base-promoted protocol for the synthesis of 2-keto(hetero)aryl benzox(thi)azoles has been developed. Starting from commercially available 2-amino(thio)phenols and alpha,alpha-dihaloketones, moderate to good yields of the corresponding heterocycles can be achieved. Notably, only EtNH2 was required as the promoter here, and the reaction can be easily performed on a large scale.

  DOI：

  10.1021/acs.joc.5b02093

文献信息

• Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles <i>via</i> redox condensation of <i>o</i>-nitrophenols with acetophenones and methylquinolines
  作者：Le Anh Nguyen、Thi Thu Tram Nguyen、Quoc Anh Ngo、Thanh Binh Nguyen

  DOI：10.1039/d1ob00976a

  日期：——

  An Fe/S catalyst generated in situ from FeCl2·4H2O and elemental sulfur S8 in the presence of a tertiary amine as a base was found to catalyze efficiently a 6e− redox condensation of o-nitrophenols with acetophenones and methylquinolines. The condensed products 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles were obtained in reasonable yields with water as the only byproduct at a temperature as low

  发现在叔胺作为碱存在下由 FeCl 2 ·4H 2 O 和元素硫 S 8原位生成的 Fe/S 催化剂可有效催化邻硝基苯酚与苯乙酮和甲基喹啉的 6e -氧化还原缩合反应。缩合产物 2-苯甲酰基苯并恶唑和 2-喹啉基苯并恶唑在低至 80 °C 的温度下以合理的收率获得，水作为唯一的副产物。
• Nickel-Catalyzed Decarboxylative Acylation of Heteroarenes by sp²CH Functionalization
  作者：Ke Yang、Cheng Zhang、Peng Wang、Yan Zhang、Haibo Ge

  DOI：10.1002/chem.201402516

  日期：2014.6.10

  azole derivatives with α‐oxoglyoxylic acids has been developed. This work represents the first example of decarboxylative cross‐coupling reactions, in a CH bond functionalization manner, through nickel catalysis, and tolerates various functional groups. Additionally, this approach provides an efficient access to azole ketones, an important structural motif in many medicinal compounds with a broad

  现已开发出镍催化的唑衍生物与α-氧代乙醛酸的无配体脱羧交叉偶联反应。这项工作代表了通过镍催化以CH键官能化方式进行的脱羧交叉偶联反应的第一个例子，并能耐受各种官能团。另外，该方法提供了对唑酮的有效利用，唑酮是许多具有广泛生物活性的药用化合物中的重要结构基序。
• Cobalt-Catalyzed Decarboxylative 2-Benzoylation of Oxazoles and Thiazoles with α-Oxocarboxylic Acids
  作者：Ke Yang、Xinyong Chen、Yuqi Wang、Wanqing Li、Adnan A. Kadi、Hoong-Kun Fun、Hao Sun、Yan Zhang、Guigen Li、Hongjian Lu

  DOI：10.1021/acs.joc.5b01450

  日期：2015.11.6

  Cobalt-catalyzed decarboxylative cross-coupling of oxazoles and thiazoles with alpha-oxocarboxylic acids was developed through an sp(2) C-H bond functionalization process. This work represents the first example of cobalt-catalyzed decarboxylative C-H bond functionalization and provides an efficient means of building some important bioactive heteroaryl ketone derivatives.