N-(tert-butyl)-5-nitrobenzo[d]oxazol-2-amine | 337908-65-3

• 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: N-(tert-butyl)-5-nitrobenzo[d]oxazol-2-amine
• 英文别名: N-tert-butyl-5-nitrobenzo[d]oxazol-2-amine；5-nitro-2-(tert-butylamino)benzoxazole；N-tert-butyl-5-nitro-1,3-benzoxazol-2-amine
• CAS: 337908-65-3
• 化学式: C₁₁H₁₃N₃O₃
• 分子量: 235.243
• InChiKey: UCMGCKLIMYTYGE-UHFFFAOYSA-N

物化性质

• 沸点：
  353.6±34.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)
• 溶解度：
  10.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-4-硝基苯酚 在 sodium azide 、 高氯酸 作用下， 以 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 53.0h， 生成 N-(tert-butyl)-5-nitrobenzo[d]oxazol-2-amine
  参考文献：
  名称：

  Voitekhovich; Gaponik; Lyakhov, Polish Journal of Chemistry, 2001, vol. 75, # 2, p. 253 - 264

  摘要：

  DOI：

文献信息

• Cobalt-Catalyzed Oxidative Isocyanide Insertion to Amine-Based Bisnucleophiles: Diverse Synthesis of Substituted 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and 2-Aminobenzoxazoles
  作者：Tong-Hao Zhu、Shun-Yi Wang、Gao-Nan Wang、Shun-Jun Ji

  DOI：10.1002/chem.201300239

  日期：2013.5.3

  Cobalt catalysis: Synthesis of substituted 2‐aminobenzimidazoles, 2‐aminobenzothiazoles, and 2‐aminobenzoxazoles was achieved by using cobalt(II) acetate catalyzed isocyanide insertion to o‐diaminobenzene, 2‐aminobenzenethiol, and 2‐aminophenol derivatives in 1,4‐dioxane (see scheme). It was found that the reaction proceeded efficiently to give the desired products in up to 95 % isolated yields by

  钴催化：使用乙酸钴（II）催化异氰酸酯插入1,4-二恶烷中的邻-二氨基苯，2-氨基苯硫醇和2-氨基苯酚衍生物，可合成取代的2-氨基苯并咪唑，2-氨基苯并噻唑和2-氨基苯并恶唑（请参阅方案）。发现该反应有效地进行，通过一步形成CN和CS（O，N），以高达95％的分离产率得到所需的产物。
• Synthesis of 2-Aminobenzoxazoles and 3-Aminobenzoxazines via Palladium-Catalyzed Aerobic Oxidation of <i>o</i>-Aminophenols with Isocyanides
  作者：Bifu Liu、Meizhou Yin、Hanling Gao、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/jo400002f

  日期：2013.4.5

  A Pd-catalyzed aerobic oxidation of o-aminophenols and isocyanides for the synthesis of 2-aminobenzoxazoles and 3-aminobenzoxazines has been achieved in an air atmosphere. The procedure constructs 2-aminobenzoxazoles and 3-aminobenzoxazines with moderate to excellent yields and a broad substrate scope. Apart from experimental simplicity, this methodology has the advantages of mild reaction conditions and easily accessible starting materials. Furthermore, the utility of this method has also been successfully applied to the synthesis of other types of useful nitrogen heterocycles.
• Cobalt(II)-Catalyzed Isocyanide Insertion Reaction with Amines under Ultrasonic Conditions: A Divergent Synthesis of Ureas, Thioureas and Azaheterocycles
  作者：Tong-Hao Zhu、Xiao-Ping Xu、Jia-Jia Cao、Tian-Qi Wei、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1002/adsc.201300745

  日期：2014.2.10

  AbstractCobalt(II) acetylacetonate‐catalyzed isocyanide insertion reactions with amines utilizing tert‐butyl hydroperoxide (TBHP) as an oxidant under ultrasound conditions have been developed, which lead to the synthesis of ureas, thioureas, as well as 2‐aminobenzimidazoles, 2‐aminobenzothiazoles, and 2‐aminobenzoxazoles under the general reaction conditions in up to 96% yields, respectively. The intermediate amino methylidyneaminiums, initiated by cobalt(II) acetylacetonate‐catalyzed reactions of isocyanides with amines, could be easily trapped by different nucleophiles such as water, sulfur, and intramolecular nucleophilic functional groups. This method provides a simple, general and practical protocol for the divergent synthesis of ureas, thioureas and azaheterocycles.magnified image
• Cobalt-Catalyzed Aerobic Oxidative Cyclization of 2-Aminophenols with Isonitriles: 2-Aminophenol Enabled O₂ Activation by Cobalt(II)
  作者：Jiaqi Liu、Jessica M. Hoover

  DOI：10.1021/acs.orglett.9b01384

  日期：2019.6.21

  An aerobic cobalt-catalyzed oxidative cyclization of 2-aminophenols and isonitriles is reported. These additive-free conditions furnish a variety of substituted 2-aminobenzoxazoles in moderate to excellent yields. A series of control experiments and spectroscopic studies point to the importance of 2-aminophenol coordination in enabling the aerobic oxidation of cobalt(II).
• Voitekhovich; Gaponik; Lyakhov, Polish Journal of Chemistry, 2001, vol. 75, # 2, p. 253 - 264
  作者：Voitekhovich、Gaponik、Lyakhov、Ivashkevich

  DOI：——

  日期：——