4-azido-5-formyl-2-phenylthiazole | 115437-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-azido-5-formyl-2-phenylthiazole
• 英文别名: 4-Azido-2-phenyl-1,3-thiazole-5-carbaldehyde
• CAS: 115437-26-8
• 化学式: C₁₀H₆N₄OS
• 分子量: 230.25
• InChiKey: YKCXLXXNNGVOOE-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C (decomp)(Solvent: Acetone)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-azido-5-formyl-2-phenylthiazole 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 5-<(N-p-tolylimino)methyl>-2-phenyl-4-<(triphenylphosphoranylidene)amino>thiazole
  参考文献：
  名称：

  Fused pyrimidines by a tandem aza-Wittig/electrocyclic ring closure strategy: synthesis of pyrazolo[3,4-d]pyrimidine, [1,2,3]triazolo[4,5-d]pyrimidine, and thiazolo[4,5-d]pyrimidine derivatives

  摘要：

  DOI：

  10.1021/jo00255a003
• 作为产物：
  描述：

  4-chloro-2-phenyl-thiazole-5-carbaldehyde 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以78%的产率得到4-azido-5-formyl-2-phenylthiazole
  参考文献：
  名称：

  Fused pyrimidines by a tandem aza-Wittig/electrocyclic ring closure strategy: synthesis of pyrazolo[3,4-d]pyrimidine, [1,2,3]triazolo[4,5-d]pyrimidine, and thiazolo[4,5-d]pyrimidine derivatives

  摘要：

  DOI：

  10.1021/jo00255a003

文献信息

• Syntheses of<i>o</i>-Aminohetarenecarbaldehydes via Azides
  作者：Jan Becher、Krystian Pluta、Niels Krake、Klaus Brøndum、Nils Just Christensen、Maria Victoria Vinader

  DOI：10.1055/s-1989-27307

  日期：——

  o-Chlorohetarenecarbaldehydes react with sodium azide at low temperature yielding moderately stable o-azidohetarenecarbaldehydes. With hydrogen sulfide these compounds are reduced to the corresponding stable o-amino aldehydes. Both reaction steps give high yields.

  o-氯杂环甲醛在低温下与叠氮化钠反应，生成中等稳定性的o-叠氮杂环甲醛。与硫化氢反应时，这些化合物被还原为相应的稳定o-氨基醛。两个反应步骤均可获得高产率。
• New Applications of the Imine-Ketenimine Intramolecular [2+2] Cycloaddition Reaction: Highly Stereocontrolled Synthesis of Azeto[1,2-a]pyrimidines
  作者：Mateo Alajarín、Angel Vidal、Raúl-Angel Orenes

  DOI：10.1002/1099-0690(200212)2002:24<4222::aid-ejoc4222>3.0.co;2-m

  日期：2002.12

  functionalities are linked by an allylic tether connecting the imino and ketenimino nitrogen atoms, undergo a formal intramolecular [2+2] cycloaddition to yield azeto[1,2-a]pyrimidines 8. When enantiotopic ketenimine and imine fragments are combined, the resulting azeto[1,2-a]pyrimidines 8e−i contain two stereogenic carbon atoms C-6 and C-7, and the cycloaddition takes place with complete diastereoselectivity

  亚氨基-烯酮亚胺 7，其中反应性官能团通过连接亚氨基和烯酮亚胺氮原子的烯丙基系链连接，经过正式的分子内 [2+2] 环加成生成氮杂 [1,2-a] 嘧啶 8。和亚胺片段结合，所得的氮杂[1,2-a]嘧啶8e-i含有两个立体碳原子C-6和C-7，并且环加成以完全非对映选择性发生，有利于顺式非对映异构体。这种方法也已应用于一些 azeto [1,2-a][1,3] 噻唑并 [4,5-d] 嘧啶 16 的制备，这是一种新的稠合杂环系统的代表性例子。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002)
• Synthetic applications of bis(iminophosphoranes). One-pot preparation of rigid bicyclic guanidines
  作者：Pedro Molina、Mateo Alajarin、Angel Vidal

  DOI：10.1021/jo00059a015

  日期：1993.3

  A one-pot synthesis of [6 + 6], [6 + 7], and [6 + 8] bicyclic guanidines based on a new method of dihydropyrimido annelation, which involves reaction of bis(iminophosphoranes) with aryl isocyanates or isothiocyanates is described. The method is also applicable for the preparation of chiral bicyclic guanidines.
• Neighbouring group effects on rates of thermolysis of 4-azidothiazoles
  作者：Erik Ceulemans、Karin Vercauteren、Leonard K. Dyall、Dirk Buelens、Wim Dehaen

  DOI：10.1016/s0040-4020(97)00638-8

  日期：1997.7

  Rate measurements for thermolysis of 4-azidothiazoles in p-xylene solution have identified neighbouring group effects from nitro (19-fold rate increase), phenyliminomethyl (16), formyl (4.5) and acetyl (2.2) substituents in the 5-position. These effects are very similar in magnitude to those measured for 3-azidothiophenes, whereas in azidobenzenes the rate increases are much larger, 5-Substituents in 4-azidothiazole which are capable of conjugative donation (phenyl, ethyl propenoate) also increased the reaction rate. The reactions involving neighbouring group participation led to cyclized products from the 4-azidothiazoles though not all of these products were stable under the thermolysis conditions. (C) 1997 Elsevier Science Ltd.
• Synthetic applications of bis(iminophosphoranes). An efficient and general route to fully unsaturated azolo-fused 1,3-diazepines
  作者：Pedro Molina、Antonio Arques、Asuncion Alias

  DOI：10.1021/jo00071a043

  日期：1993.9