benzo[d]oxazole | 1404370-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: benzo[d]oxazole
• 英文别名: 5-p-tolylbenzoxazole；5-(4-Methylphenyl)-1,3-benzoxazole
• CAS: 1404370-63-3
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: JKOXHJBGQBAJND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzo[d]oxazole 、 二甲胺基磺酰氯 在 potassium dichromate 、 (2,2-联吡啶)二氯钯(II) 、 copper(l) cyanide 、 potassium carbonate 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以83%的产率得到N,N-dimethyl-5-p-tolylbenzo[d]oxazol-2-amine
  参考文献：
  名称：

  Palladium–copper-catalyzed desulfitative amination of benzo[d]oxazole C–H bond

  摘要：

  An efficient palladium-copper-catalyzed direct C-H amination of substituted benzoxazoles with various sulfamoyl chlorides as nitrogen group sources has been developed. The system does not need a strong base and tolerates a series of functional groups, such as chloro, methyl, and nitro groups, providing the amination products in moderate to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.044
• 作为产物：
  描述：

  4-甲苯硼酸 、 5-氯苯并唑 在 potassium phosphate 、 4-甲氧基苯硼酸 、 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到benzo[d]oxazole
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of Polyfluorinated Arenes with Heteroarenes via C–F/C–H Activation

  摘要：

  The first palladium-catalyzed coupling of 2-pyrldyl-polyfluoroarenes and benzoxazole, thiazole, benzothiazole, benzoimidazole, oxazole or oxadiazole via a concurrent C-F/C-H activation is described. Initial mechanistic studies showed that C-F activation of perfluoroarene is likely the rate-limiting step of the catalytic cycle. This protocol provides a useful and operationally simple process to functionalized polyfluoroarenes.

  DOI：

  10.1021/ol303567t

文献信息

• The palladium-catalyzed tandem decarboxylation, carbon–carbon triple bond oxidation and decarbonylative arylation of the benzoxazole C–H bond
  作者：Dongfang Liu、Bin Liu、Jiang Cheng

  DOI：10.1039/c3ra41185k

  日期：——

  A palladium-catalyzed arylation of benzoxazole has been developed. This protocol involves the tandem decarboxylation and oxidation of a carbon–carbon triple bond followed by decarbonylative arylation of the benzoxazole C–H bond.

  开发了一种钯催化的苯并恶唑芳基化反应。该方案涉及碳-碳三键的串联脱羧和氧化，随后是苯并恶唑C-H键的脱羰基芳基化。
• Unexpected TFA-catalyzed tandem reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids: synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones and cephalandole A
  作者：Shaoxi Yan、Leping Ye、Miaochang Liu、Jiuxi Chen、Jinchang Ding、Wenxia Gao、Xiaobo Huang、Huayue Wu

  DOI：10.1039/c4ra01605j

  日期：——

  TFA-catalyzed reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids: synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones and the natural product cephalandole A.

  TFA催化的苯并[d]噁唑与2-氧代-2-芳基乙酸的反应：3-芳基-2H-苯并[b][1,4]噁唑-2-酮和天然产物头脑醇A的合成。
• ANALOGS OF FEXARAMINE AND METHODS OF MAKING AND USING
  申请人：Salk Institute for Biological Studies

  公开号：US20170066724A1

  公开（公告）日：2017-03-09

  Novel compounds having a formula embodiments of a method of making the same, and of a composition comprising them are disclosed herein. Also disclosed are embodiments of a method of treating or preventing a metabolic disorder in a subject, comprising administering to a subject (e.g., via the gastrointestinal tract) a therapeutically effective amount of one or more of the disclosed compounds, thereby activating FXR receptors in the intestines, and treating or preventing a metabolic disorder in the subject. Additionally disclosed are embodiments of a method of treating or preventing inflammation in an intestinal region of a subject, comprising administering to the subject (e.g., via the gastrointestinal tract) a therapeutically effective amount of one or more of the disclosed compounds, thereby activating FXR receptors in the intestines, and thereby treating or preventing inflammation in the intestinal region of the subject.
• [EN] ANALOGS OF FEXARAMINE AND METHODS OF MAKING AND USING<br/>[FR] ANALOGUES DE LA FEXARAMINE ET LEUR PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：SALK INST FOR BIOLOGICAL STUDI

  公开号：WO2017078927A1

  公开（公告）日：2017-05-11

  Novel compounds having a formula (I), embodiments of a method of making the same, and of a composition comprising them are disclosed herein. Also disclosed are embodiments of a method of treating or preventing a metabolic disorder in a subject, comprising administering to a subject (e.g., via the gastrointestinal tract) a therapeutically effective amount of one or more of the disclosed compounds, thereby activating FXR receptors in the intestines, and treating or preventing a metabolic disorder in the subject. Additionally disclosed are embodiments of a method of treating or preventing inflammation in an intestinal region of a subject, comprising administering to the subject (e.g., via the gastrointestinal tract) a therapeutically effective amount of one or more of the disclosed compounds, thereby activating FXR receptors in the intestines, and thereby treating or preventing inflammation in the intestinal region of the subject.
• Palladium-Catalyzed Coupling of Polyfluorinated Arenes with Heteroarenes via C–F/C–H Activation
  作者：Daohong Yu、Long Lu、Qilong Shen

  DOI：10.1021/ol303567t

  日期：2013.2.15

  The first palladium-catalyzed coupling of 2-pyrldyl-polyfluoroarenes and benzoxazole, thiazole, benzothiazole, benzoimidazole, oxazole or oxadiazole via a concurrent C-F/C-H activation is described. Initial mechanistic studies showed that C-F activation of perfluoroarene is likely the rate-limiting step of the catalytic cycle. This protocol provides a useful and operationally simple process to functionalized polyfluoroarenes.