5-(thiazol-2-yl)furan-2-carbaldehyde | 342601-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(thiazol-2-yl)furan-2-carbaldehyde
• 英文别名: 5-(1,3-thiazol-2-yl)furan-2-carbaldehyde
• CAS: 342601-01-8
• 化学式: C₈H₅NO₂S
• 分子量: 179.199
• InChiKey: LDTADWAOSPRJTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(thiazol-2-yl)furan-2-carbaldehyde 、 4-methyl-N-(4-oxo-1,3-thiazolidin-2-ylidene)benzamide 在 哌啶 作用下， 以 正丁醇 为溶剂， 反应 2.0h， 生成 4-methyl-N-[(5Z)-4-oxo-5-[[5-(1,3-thiazol-2-yl)furan-2-yl]methylidene]-1,3-thiazolidin-2-ylidene]benzamide
  参考文献：
  名称：

  Synthesis of thiazolone-based sulfonamides as inhibitors of HCV NS5B polymerase

  摘要：

  Several thiazolone-based sulfonamides were prepared, utilizing various hetero-aryl sulfonyl chlorides and different aldehydes, as inhibitors of NS5B polymerase, to target HCV. The best compound showed 0.6 nM Of IC50 inhibitory activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.104
• 作为产物：
  描述：

  5-溴-2-呋喃甲醛 、 bromozinc(1+),2H-1,3-thiazol-2-ide 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以43%的产率得到5-(thiazol-2-yl)furan-2-carbaldehyde
  参考文献：
  名称：

  A convenient synthesis of 5-aryl- and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs

  摘要：

  An efficient synthetic route for the preparation of 5-heteroaryl- and 5-aryl-2-furaldehydes has been developed. It has been accomplished by the palladium(0)-catalyzed cross-coupling reaction of heteroarylzinc and arylzinc reagents with 5-bromo-2-furaldehyde under very mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.035

文献信息

• Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement
  作者：Alfonso Zambon、Giuseppe Borsato、Stefania Brussolo、Pietrogiulio Frascella、Vittorio Lucchini

  DOI：10.1016/j.tetlet.2007.11.029

  日期：2008.1

  A novel rearrangement process involving the migration of trimethylstannanyl or trimethylsilanyl groups around the thiazole ring provides access to either 2- or 5-metallated thiazoles by tuning the reaction conditions. The proposed mechanism, based on experimental evidence, is characterized by the catalytic role of thiazole bisadducts as metal-transfer agents.

  涉及三甲基锡烷基或三甲基硅烷基在噻唑环周围迁移的新颖的重排过程可通过调节反应条件来获得2-或5-金属化的噻唑。根据实验证据，所提出的机理的特征在于噻唑二加合物作为金属转移剂的催化作用。
• GAMMA-HYDROXY-2-(FLUOROALKYLAMINOCARBONYL)-1-PIPERAZINEPENTANAMIDES AS HIV PROTEASE INHIBITORS
  申请人：Merck & Co., Inc.

  公开号：EP1242426B1

  公开（公告）日：2007-10-31
• Synthesis of thiazolone-based sulfonamides as inhibitors of HCV NS5B polymerase
  作者：Yili Ding、Kenneth L. Smith、Chamakura V.N.S. Varaprasad、Eugene Chang、John Alexander、Nanhua Yao

  DOI：10.1016/j.bmcl.2006.08.104

  日期：2007.2

  Several thiazolone-based sulfonamides were prepared, utilizing various hetero-aryl sulfonyl chlorides and different aldehydes, as inhibitors of NS5B polymerase, to target HCV. The best compound showed 0.6 nM Of IC50 inhibitory activity. (c) 2006 Elsevier Ltd. All rights reserved.
• A convenient synthesis of 5-aryl- and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tetlet.2010.03.035

  日期：2010.5

  An efficient synthetic route for the preparation of 5-heteroaryl- and 5-aryl-2-furaldehydes has been developed. It has been accomplished by the palladium(0)-catalyzed cross-coupling reaction of heteroarylzinc and arylzinc reagents with 5-bromo-2-furaldehyde under very mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.