5-氯-N-(苯基甲基)-1,3-苯并恶唑-2-胺 | 78749-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 5-氯-N-(苯基甲基)-1,3-苯并恶唑-2-胺
• 英文名称: N-benzyl-5-chlorobenzo[d]oxazol-2-amine
• 英文别名: 2-(Benzylamino)-5-chlorobenzoxazole；N-benzyl-5-chloro-1,3-benzoxazol-2-amine
• CAS: 78749-89-0
• 化学式: C₁₄H₁₁ClN₂O
• mdl: MFCD01664148
• 分子量: 258.707
• InChiKey: PALYRMSPZVOLCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  38.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯化苄 、 5-氯-N-(苯基甲基)-1,3-苯并恶唑-2-胺 反应 15.0h， 以80%的产率得到Benzyl-[3-benzyl-5-chloro-3H-benzooxazol-(2E)-ylidene]-amine
  参考文献：
  名称：

  Yamato, Masatoshi; Takeuchi, Yasuo; Hattori, Kyoko, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 8, p. 3053 - 3060

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Benzyl-3-(5-chlor-2-hydroxyphenyl)-2-thiocarbamid 在 ammonium hydroxide 、 silver nitrate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到5-氯-N-(苯基甲基)-1,3-苯并恶唑-2-胺
  参考文献：
  名称：

  Synthesis and IR spectra of some 2-aminobenzoxazole derivatives

  摘要：

  DOI：

  10.1007/bf00505682

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。
• An economically and environmentally sustainable synthesis of 2-aminobenzothiazoles and 2-aminobenzoxazoles promoted by water
  作者：Xinying Zhang、Xuefei Jia、Jianji Wang、Xuesen Fan

  DOI：10.1039/c0gc00418a

  日期：——

  Tandem reactions of isothiocyanates (1) with 2-aminothiophenols (2), or isothiocyanates (1) with 2-aminophenols (4), were carried out rapidly and efficiently in water. A significant rate acceleration of the reaction between 1a and 2a in water compared with commonly used volatile organic solvents was observed. Through these reactions, a variety of structurally and pharmaceutically interesting 2-aminobenzothiazoles

  的串联反应 异硫氰酸酯（1）与2-氨基苯硫酚（2）或异硫氰酸酯（1）与2-氨基酚（4）一起快速高效地进行了分离。水。之间的反应的甲显著速率加速度1A和2A中水 与常用的挥发性有机物相比 溶剂被观测到。通过这些反应，以高收率合成了各种结构上和药学上令人关注的2-氨基苯并噻唑（3）和2-氨基苯并恶唑（5）。这种针对3和5的新颖合成方法具有诸如高效率，易于获得的起始原料，对环境无害的优点。溶剂，以及高度简单实用的实验程序。
• 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。
• Benzoxazoles: Potent Skeletal Muscle Relaxants
  作者：Joseph Sam、James N. Plampin

  DOI：10.1002/jps.2600530518

  日期：1964.5
• A Mild and Efficient One-Pot Synthesis of 2-Aminated Benzoxazoles and Benzothiazoles
  作者：Gavin W. Stewart、Carl A. Baxter、Ed Cleator、Faye J. Sheen

  DOI：10.1021/jo900308t

  日期：2009.4.17

  Previous syntheses of the biologically active 2-aminated benzoxazoles have relied on forcing thermal conditions to generate the products directly from the corresponding thiols. The resulting yields have ranged from moderate to poor. A mild and high-yielding alternative one-pot chlorination-amination procedure is described. Compounds with a variety of substitution patterns are reported and the methodology has been successfully extended to benzothiazoles. Palladium catalysis on suitably activated examples has been employed to generate the desired compounds of interest.