2-methylsulfanyl-4-(2-phenylthiazol-4-yl)-pyrimidine | 1092073-95-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methylsulfanyl-4-(2-phenylthiazol-4-yl)-pyrimidine
• 英文别名: 4-(2-Methylsulfanylpyrimidin-4-yl)-2-phenyl-1,3-thiazole；4-(2-methylsulfanylpyrimidin-4-yl)-2-phenyl-1,3-thiazole
• CAS: 1092073-95-4
• 化学式: C₁₄H₁₁N₃S₂
• 分子量: 285.393
• InChiKey: NRUDNWMCHLGPBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-phenyl-4-(tributylstannyl)thiazole 、 2-甲硫基-4-氯嘧啶 在 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以78%的产率得到2-methylsulfanyl-4-(2-phenylthiazol-4-yl)-pyrimidine
  参考文献：
  名称：

  A guideline for the arylation of positions 4 and 5 of thiazole via Pd-catalyzed cross-coupling reactions

  摘要：

  The arylation of thiazoles in 4- and 5-position was investigated in detail. Suzuki-Miyaura and Stille cross-coupling reactions were tested using thiazoles either as halide or organometal species. The obtained results were critically compared to develop helpful guidelines for selection of the cross-coupling methodology with the best potential for good and reliable results for a given synthetic problem without the need for tedious optimization of reaction parameters. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.081

文献信息

• A Comparative Study on Stille Cross-Coupling Reactions of 2-Phenylthiazoles and 2-Phenyloxazoles
  作者：Peter Stanetty、Johanna Hämmerle、Markus Spina、Michael Schnürch、Marko Mihovilovic

  DOI：10.1055/s-2008-1067263

  日期：2008.10

  A systematic study of the cross-coupling capability of the 4- and 5-positions of 2-phenylthiazoles and -oxazoles under Stille conditions is presented. The azoles were both applied as stannanes and as the halide component. The obtained results were compared regarding the position of the halide and Bu3Sn group. In order to establish a general reactivity platform for those heterocyclic systems, a broad variety of aromatic and heteroaromatic halides were coupled and some significant differences concerning the coupling properties of the investigated systems were observed.

  本文系统研究了在Stille条件下2-苯基噻唑和-噁唑的4位和5位的交叉偶联能力。噁唑既可用作锡烷，也可用作卤化物成分。将所得结果与卤化物和Bu3Sn基团的位置进行了比较。为了建立这些杂环系统的通用反应平台，对多种芳香和杂芳卤化物进行了偶联，并观察到所研究系统的偶联性质存在一些显著差异。