N-benzyl-5-methyl-4-phenylthiazol-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzyl-5-methyl-4-phenylthiazol-2-amine
• 英文别名: 2-benzylamino-5-methyl-4-phenylthiazole；benzyl-(5-methyl-4-phenyl-thiazol-2-yl)-amine；N-benzyl-5-methyl-4-phenyl-1,3-thiazol-2-amine
• 化学式: C₁₇H₁₆N₂S
• mdl: MFCD06367638
• 分子量: 280.393
• InChiKey: ONXFQXKOJJHSDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.117
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯丙酮 在 溴 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 生成 N-benzyl-5-methyl-4-phenylthiazol-2-amine
  参考文献：
  名称：

  Substituted 2-aminothiazoles are exceptional inhibitors of neuronal degeneration in tau-driven models of Alzheimer’s disease

  摘要：

  A novel series of 2-aminothiazoles with strong protection in an Alzheimer's disease (AD) model comprising tau-induced neuronal toxicity is disclosed. These derivatives can be synthesized in one-pot and a small SAR of the substitution within these series afforded several compounds that counteracted tau-induced cell toxicity at nanomolar concentrations. These congeners therefore have strong potential as possible treatment for Alzheimer's disease and other related tauopathies. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2011.05.014

文献信息

• Microwave-Assisted Domino Reactions of Propargylamines with Isothiocyanates: Selective Synthesis of 2-Aminothiazoles and 2-Amino-4-methylenethiazolines
  作者：Daniele Castagnolo、Nicoló Scalacci、Chiara Pelloja、Marco Radi

  DOI：10.1055/s-0035-1561985

  日期：——

  versatile microwave-assisted protocol for the synthesis of 2-aminothiazoles has been developed. The domino reaction of propargylamines and isothiocyanates in the presence of catalytic PTSA leads to the selective synthesis of 2-aminothiazoles at temperatures above 130 °C and in a few minutes. The same reaction carried out at lower temperatures leads to the formation of the tautomeric 2-amino-4-methylenethiazolines

  已开发出一种用于合成 2-氨基噻唑的简单且通用的微波辅助方案。在催化 PTSA 存在下炔丙胺和异硫氰酸酯的多米诺反应导致在 130°C 以上的温度下在几分钟内选择性合成 2-氨基噻唑。在较低温度下进行的相同反应导致形成互变异构的 2-氨基-4-亚甲基噻唑啉。
• Regioselective N-alkylation of 2-amino-azoles with alcohols for the synthesis of 2-N-(alkylamino)azoles catalyzed by a ruthenium complex bearing a functional ligand
  作者：Xiangchao Xu、Yawen Tang、Jin Zhang、Beixuan Dong、Feng Li

  DOI：10.1016/j.jcat.2023.06.022

  日期：2023.10

  functional ligand [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the direct N-alkylation of 2-amino-azoles with alcohols to 2-(N-alkylamino)zoles. In the presence of catalyst (0.5 mol %), a range of desirable products were obtained with complete regioselectivity. Mechanistic experiments supported that functional groups in bpy ligand are crucially important for the catalytic

  带有功能配体的钌络合物[( p-伞花烃)Ru(2,2'-bpyO)(H 2 O)]被发现是一种通用且有效的催化剂，用于2-氨基唑类的直接N-烷基化醇至2-(N-烷基氨基)唑。在催化剂（0.5 mol%）存在下，获得了一系列具有完全区域选择性的理想产物。机理实验表明，bpy 配体中的官能团对于钌配合物的催化活性至关重要。值得注意的是，这项研究将促进氢自转移过程金属配体双功能催化剂的进展。
• One pot synthesis using supported reagents system KSCN/SiO2–RNH3OAc/Al2O3: synthesis of 2-aminothiazoles and N-allylthioureas
  作者：Tadashi Aoyama、Sumiko Murata、Izumi Arai、Natsumi Araki、Toshio Takido、Yoshitada Suzuki、Mitsuo Kodomari

  DOI：10.1016/j.tet.2006.01.075

  日期：2006.4

  A simple and efficient method has been developed for the synthesis of 2-aminothiazoles and N-allylthioureas from commercially available materials in one pot by using a supported reagents system, KSCN/SiO2-RNH3OAc/Al2O3, in which alpha-halo ketone reacts first KSCN/SiO2 and the product, alpha.-thiocyanatoketone, reacts with RNH3OAc/Al2O3 to give the final product, 2-aminothiazoles, in good yield and allyl bromide reacts with KSCN/SiO2 and the product, allyl isothiocyanate, reacts with RNH3OAc/Al2O3 to give N-allylthiourea. (c) 2006 Elsevier Ltd. All rights reserved.
• Expedient Synthesis of N-Substituted 2-Aminothiazoles
  作者：Joachim G. Schantl、Irene M. Lagoja

  DOI：10.1080/00397919808006844

  日期：1998.4

  The reaction of alpha-halo ketones 1 with potassium thiocyanate and amines 3 offers the advantage of an efficient one-pot synthesis of the title compounds 4 from readily available starting materials.
• Substituted 2-aminothiazoles are exceptional inhibitors of neuronal degeneration in tau-driven models of Alzheimer’s disease
  作者：Irene Lagoja、Christophe Pannecouque、Gerard Griffioen、Stefaan Wera、Veronica Maria Rojasdelaparra、Arthur Van Aerschot

  DOI：10.1016/j.ejps.2011.05.014

  日期：2011.8

  A novel series of 2-aminothiazoles with strong protection in an Alzheimer's disease (AD) model comprising tau-induced neuronal toxicity is disclosed. These derivatives can be synthesized in one-pot and a small SAR of the substitution within these series afforded several compounds that counteracted tau-induced cell toxicity at nanomolar concentrations. These congeners therefore have strong potential as possible treatment for Alzheimer's disease and other related tauopathies. (C) 2011 Elsevier B.V. All rights reserved.