烯丙基-(4-苯基-噻唑-2-基)-胺 | 21344-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 烯丙基-(4-苯基-噻唑-2-基)-胺
• 英文名称: 2-allylamino-4-phenylthiazole
• 英文别名: N-allyl-4-phenylthiazol-2-amine；Allyl-(4-phenyl-thiazol-2-yl)-amine；4-phenyl-N-prop-2-enyl-1,3-thiazol-2-amine
• CAS: 21344-73-0
• 化学式: C₁₂H₁₂N₂S
• mdl: MFCD00744761
• 分子量: 216.307
• InChiKey: FREHXEYAZAQJFE-UHFFFAOYSA-N

物化性质

• 熔点：
  73 °C(Solv: ethanol (64-17-5))
• 沸点：
  357.5±45.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090

反应信息

• 作为产物：
  描述：

  苯乙酮 在 potassium carbonate 、 copper(I) bromide 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 烯丙基-(4-苯基-噻唑-2-基)-胺
  参考文献：
  名称：

  Facile One-Pot Procedure for the Synthesis of 2-Aminothiazole Derivatives

  摘要：

  A facile, efficient synthesis of 2-aminothiazole derivatives by the reaction of easily available aromatic methyl ketones with thiourea/N-substituted thioureas in the presence of copper(II) bromide was developed. The reaction underwent a one-pot alpha-bromination/cyclization process.

  DOI：

  10.3987/com-12-12510

文献信息

• One-pot synthesis of 4-aryl-2-aminothiazoles from styrenes and thioureas promoted by tribromoisocyanuric acid
  作者：Vitor S.C. de Andrade、Marcio C.S. de Mattos

  DOI：10.1016/j.tetlet.2020.152164

  日期：2020.7

  A simple and efficient one-pot protocol has been developed for the conversion of styrenes into 4-aryl-2-aminothiazoles using readily available starting materials. Tribromoisocyanuric acid was successfully used for the co-bromination and oxidation of styrenes to give phenacyl bromides, which in the presence of thioureas produced the corresponding 4-aryl-2-aminothiazoles in 48–70% yield. The protocol

  已经开发出一种简单有效的一锅法，用于使用容易获得的起始原料将苯乙烯转化为4-芳基-2-氨基噻唑。三溴异氰尿酸已成功用于苯乙烯的共溴化和氧化，得到苯甲酰溴，在硫脲存在下，苯甲酰苯能以48-70％的产率产生相应的4-芳基-2-氨基噻唑。该方案在一个过程中涉及三个反应：串联（由苯乙烯形成苯甲酰溴），然后进行伸缩（转化为噻唑）反应。
• Synthesis of a Thiazole Library via an Iridium-Catalyzed Sulfur Ylide Insertion Reaction
  作者：Storm Hassell-Hart、Elisa Speranzini、Sirihathai Srikwanjai、Euan Hossack、S. Mark Roe、Daren Fearon、Daniel Akinbosede、Stephen Hare、John Spencer

  DOI：10.1021/acs.orglett.2c02996

  日期：2022.11.4

  A library of thiazoles and selenothiazoles were synthesized via Ir-catalyzed ylide insertion chemistry. This process is a functional group, particularly heterocycle-substituent tolerant. This was applied to the synthesis of fanetizole, an anti-inflammatory drug, and a thiazole-containing drug fragment that binds to the peptidyl-tRNA hydrolase (Pth) in Neisseria gonorrheae bacteria.

  通过 Ir 催化叶立德插入化学合成了噻唑和硒代噻唑库。这个过程是一个官能团，特别是杂环取代基的耐受性。该技术被应用于合成抗炎药法奈替唑以及与淋病奈瑟菌细菌中的肽基-tRNA水解酶（Pth）结合的含噻唑药物片段。
• ——
  作者：S. I. Zav'yalov、O. V. Dorofeeva、E. E. Rumyantseva、L. B. Kulikova、G. I. Ezhova、N. E. Kravchenko、A. G. Zavozin

  DOI：10.1023/a:1010477022450

  日期：——
• 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.
• v. Walther; Roch, Journal fur praktische Chemie (Leipzig 1954), 1913, vol. <2> 87, p. 61
  作者：v. Walther、Roch

  DOI：——

  日期：——