N-(3-benzylthiazole-2(3H)-ylidene)aniline | 1290104-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-benzylthiazole-2(3H)-ylidene)aniline
• 英文别名: N-[3-benzylthiazol-2(3H)-ylidene]aniline；3-benzyl-N-phenylthiazol-2(3H)-imine；3-benzyl-N-phenyl-1,3-thiazol-2-imine
• CAS: 1290104-79-8
• 化学式: C₁₆H₁₄N₂S
• 分子量: 266.367
• InChiKey: ISOYGZVWGGRWJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  间氯溴苯 、 N-(3-benzylthiazole-2(3H)-ylidene)aniline 在 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以58%的产率得到
  参考文献：
  名称：

  通过直接芳基化合成内-和外-N-保护的 5-芳基化 2-氨基噻唑：细胞分化加速剂的有效途径

  摘要：

  报告了使用芳基溴作为芳基供体直接芳基化 N-苯基-N-苄基（噻唑-2-基）胺的改进方案。该程序与之前报道的使用芳基碘化物作为芳基化剂的方案进行了比较。改进的直接芳基化方案应用于结构异构和非芳香族 3-苄基-N-苯基噻唑-2(3H)-亚胺。用于直接芳基化的两种底物是从共同的起始原料 N-苯基（噻唑-2-基）胺获得的，该原料通过使用两组反应条件在环外或环内氮上进行区域选择性苄化。对于异构的非芳香族 3-苄基-N-苯基噻唑-2(3H)-亚胺的芳基化，可以在 5 位实现独特的区域选择性。

  DOI：

  10.1002/ejoc.201500283
• 作为产物：
  描述：

  苯胺 在 对甲苯磺酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 反应 72.0h， 生成 N-(3-benzylthiazole-2(3H)-ylidene)aniline
  参考文献：
  名称：

  Synthesis of 5-arylated N-arylthiazole-2-amines as potential skeletal muscle cell differentiation promoters

  摘要：

  A series of N-arylthiazole-2-amines was prepared and their biological activity for the promotion of skeletal muscle cell differentiation was investigated, a process of significant importance in muscle regeneration. A versatile new synthetic route towards the target compounds was developed and the substrate scope of this methodology was investigated. Introduction of the 2-aminoaryl substituent was carried out via nucleophilic substitution reactions in excellent yields. Furthermore, the aryl in 5-position was introduced applying a direct arylation reaction, a major improvement compared to reported synthetic routes regarding atom efficiency and sustainability. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.123

文献信息

• Efficient One-Pot Synthesis of Thiazol-2-imine Derivatives through Regioselective Reaction Between Primary Amines, Phenylisothiocyanate, and α-Chloroacetaldehyde
  作者：Farough Nasiri、Leila Sabahi-Agabager

  DOI：10.2174/1568009617666161107093942

  日期：2017.3.23

  A literature survey reveals that there have been no any reports on the synthesis of thiazol-2-imine derivatives without substituents in position C-4 and C-5 via one-pot reaction. Herein we report an efficient one-pot route for synthesis of these compounds in good to high yields. MATERIALS AND METHOD To a stirred mixture of amine (1 mmol) and phenylisothiocyanate (1 mmol) in EtOH (2 ml), KI (0.1 mmol)

  目的和目的噻唑-2-亚胺衍生物对它们的药物和生物活性很感兴趣。文献调查表明，没有关于通过一锅法反应在C-4和C-5位上具有取代基的噻唑-2-亚胺衍生物的合成的任何报道。在这里，我们报告了一种有效的一锅法合成这些化合物的方法，产率高到高。材料与方法在回流条件下，向胺（1 mmol）和异硫氰酸苯酯（1 mmol）在EtOH（2 ml）中的搅拌混合物中加入KI（0.1 mmol）和DABCO（0.2 mmol）。然后将α-氯乙醛（2mmol）逐滴加入到反应混合物中。反应完成后，将产物在硅胶短柱上纯化（EtOAc /正己烷，1∶9）。结果伯胺，异氰酸苯酯，α-氯乙醛在各种碱和KI的存在下于不同溶剂中进行。发现当温度达到EtOH的沸点时获得最大的产率。比较在各种碱存在下在回流下在EtOH，CH3CN，THF，CH2Cl2和H2O中的反应结果，证明在DABCO存在下在EtOH中的反应收率是最有效的。当
• Synthesis of 5-arylated N-arylthiazole-2-amines as potential skeletal muscle cell differentiation promoters
  作者：Michael Schnürch、Birgit Waldner、Karlheinz Hilber、Marko D. Mihovilovic

  DOI：10.1016/j.bmcl.2011.01.123

  日期：2011.4

  A series of N-arylthiazole-2-amines was prepared and their biological activity for the promotion of skeletal muscle cell differentiation was investigated, a process of significant importance in muscle regeneration. A versatile new synthetic route towards the target compounds was developed and the substrate scope of this methodology was investigated. Introduction of the 2-aminoaryl substituent was carried out via nucleophilic substitution reactions in excellent yields. Furthermore, the aryl in 5-position was introduced applying a direct arylation reaction, a major improvement compared to reported synthetic routes regarding atom efficiency and sustainability. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of<i>endo</i>- and<i>exo</i>-<i>N</i>-Protected 5-Arylated 2-Aminothiazoles through Direct Arylation: An Efficient Route to Cell Differentiation Accelerators
  作者：Toan Dao-Huy、Birgit J. Waldner、Laurin Wimmer、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1002/ejoc.201500283

  日期：2015.7

  An improved protocol for the direct arylation of N-phenyl-N-benzyl(thiazol-2-yl)amine by using aryl bromides as aryl donors is reported. The procedure was compared with a previously reported protocol in which aryl iodides were used as arylating agents. The improved direct arylation protocol was applied to structurally isomeric and nonaromatic 3-benzyl-N-phenylthiazol-2(3H)-imine. The two substrates

  报告了使用芳基溴作为芳基供体直接芳基化 N-苯基-N-苄基（噻唑-2-基）胺的改进方案。该程序与之前报道的使用芳基碘化物作为芳基化剂的方案进行了比较。改进的直接芳基化方案应用于结构异构和非芳香族 3-苄基-N-苯基噻唑-2(3H)-亚胺。用于直接芳基化的两种底物是从共同的起始原料 N-苯基（噻唑-2-基）胺获得的，该原料通过使用两组反应条件在环外或环内氮上进行区域选择性苄化。对于异构的非芳香族 3-苄基-N-苯基噻唑-2(3H)-亚胺的芳基化，可以在 5 位实现独特的区域选择性。