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

• 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-(4-methylbenzyl)benzo[d]oxazol-2-amine
• 英文别名: benzooxazol-2-yl-(4-methyl-benzyl)-amine；N-[(4-methylphenyl)methyl]-1,3-benzoxazol-2-amine
• 化学式: C₁₅H₁₄N₂O
• mdl: MFCD13239590
• 分子量: 238.289
• InChiKey: WWLKPBAXKLQSLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  38.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2'-benzooxazolyl)pyridinium aminide 以 丙酮 为溶剂， 反应 144.0h， 生成 N-(4-methylbenzyl)benzo[d]oxazol-2-amine
  参考文献：
  名称：

  Pyridinium N-(2′-Azinyl)Aminides: Regioselective Synthesis of 2-Alkylaminoazines

  摘要：

  The regioselective alkylation of pyridinium-N-(2'-azinil)aminides with alkyl halides under mild conditions is described. The alkylation, combined with a reduction of the N-N bond, allows an easy preparation of 2-alkylaminoazines. (C) 2000 Elsevier Science Ltd. AU rights reserved.

  DOI：

  10.1016/s0040-4020(00)00084-3

文献信息

• Copper-Catalyzed Direct Amination of Benzoxazoles Using Primary Amines as Nitrogen Sources
  作者：Chun Cai、Jian Gu

  DOI：10.1055/s-0034-1379886

  日期：——

  A facile, efficient, and simple protocol for direct oxidative C–H amination of benzoxazoles with primary amines through copper-catalyzed C–H bond activation using tert -butyl peroxide (TBP) as oxidant under air has been developed. The reaction proceeds smoothly at ambient temperature to furnish the products. A variety of substituted aminobenzoxazoles were synthesized with good to excellent yields.

  已经开发了一种简便、高效且简单的方案，用于在空气下使用叔丁基过氧化物 (TBP) 作为氧化剂，通过铜催化的 C-H 键活化，将苯并恶唑与伯胺直接氧化 C-H 胺化。反应在室温下平稳进行以提供产物。合成了多种取代的氨基苯并恶唑，收率良好至极好。
• Iodine-Catalyzed Amination of Benzoxazoles: A Metal-Free Route to 2-Aminobenzoxazoles under Mild Conditions
  作者：Manjunath Lamani、Kandikere Ramaiah Prabhu

  DOI：10.1021/jo201402a

  日期：2011.10.7

  route of oxidative amination of benzoxazole by activation of C–H bonds with secondary or primary amines in the presence of catalytic iodine in aqueous tert-butyl hydroperoxide proceeds smoothly at ambient temperature under neat reaction condition to furnish the high yield of the aminated product. This user-friendly method to form C–N bonds produces tertiary butanol and water as the byproduct, which are

  在叔丁基氢过氧化物水溶液中，在催化碘的存在下，在催化反应碘的存在下，通过用仲胺或伯胺活化C–H键与苯胺或伯胺活化，可以轻松实现苯并恶唑氧化胺化的简便金属途径，该条件在环境温度和纯净的反应条件下可顺利进行，以实现高收率。胺化产品。这种形成C–N键的用户友好方法会产生叔丁醇和水作为副产物，对环境无害。通过合成具有治疗活性的苯并恶唑，该方法的应用受到了破坏。
• An Efficient Solid-phase Parallel Synthesis of 2-Amino and 2-Amidobenzo[d]oxazole Derivatives via Cyclization Reactions of 2-Hydroxyphenylthiourea Resin
  作者：Se-Lin Jung、Seul-Gi Kim、Gee-Hyung Lee、Young-Dae Gong

  DOI：10.5012/bkcs.2012.33.12.4109

  日期：2012.12.20

  An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]-oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo-[d]oxazole resins 4 by cyclization reaction of 2-hydroxy-phenylthiourea resin 3. The resin-bound 2-hydroxyphenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2-amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane ($CH_2Cl_2$).

  开发了一种高效的固相合成方法，用于合成2-氨基和2-酰胺基苯并[d]噁唑衍生物。该方法的关键步骤是通过2-羟基苯硫脲树脂3的环化反应制备聚合物结合的2-氨基苯并[d]噁唑树脂4。树脂结合的2-羟基苯硫脲3是通过将2-氨基酚加到异硫氰酸酯终端树脂2上制备的，并作为接头树脂的关键中间体。这个核心骨架2-氨基苯并[d]噁唑树脂4通过与各种亲电试剂（如烷基卤化物和酰氯）进行功能化反应，分别生成2-氨基和2-酰胺基苯并[d]噁唑树脂5和6。最后，通过在二氯甲烷中使用三氟乙酸（TFA）切割相应的树脂5和6，可以高产率和纯度地得到2-氨基和2-酰胺基苯并[d]噁唑衍生物7和8。