Tert-butyl 3-[5-(thiophen-2-ylmethyl)-4,5-dihydro-1,2-oxazol-3-yl]indole-1-carboxylate | 1023294-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Tert-butyl 3-[5-(thiophen-2-ylmethyl)-4,5-dihydro-1,2-oxazol-3-yl]indole-1-carboxylate
• 英文别名: tert-butyl 3-[5-(thiophen-2-ylmethyl)-4,5-dihydro-1,2-oxazol-3-yl]indole-1-carboxylate
• CAS: 1023294-79-2
• 化学式: C₂₁H₂₂N₂O₃S
• 分子量: 382.483
• InChiKey: ATVLXMQZVAJGRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴噻吩 、 (E)-tert-butyl 3-(1-(hydroxyimino)but-3-en-1-yl)-1H-indole-1-carboxylate 在 tris(dibenzylideneacetone)dipalladium (0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以52%的产率得到Tert-butyl 3-[5-(thiophen-2-ylmethyl)-4,5-dihydro-1,2-oxazol-3-yl]indole-1-carboxylate
  参考文献：
  名称：

  Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ²-Isoxazolines

  摘要：

  A novel route to the synthesis of Delta(2)-isoxazoline derivatives is described. Reaction of beta,gamma-unsaturated oximes with aryl bromides via palladium-catalyzed carboetherification affords 3,5-disubstituted Delta(2)-isoxazolines in good yields. The use of Xantphos as ligand is crucial for the transformation. The carboetherification products can be further converted to beta-hydroxy ketones in the presence of Fe powder and NH(4)Cl.

  DOI：

  10.1021/ol8002173

文献信息

• Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ²-Isoxazolines
  作者：Dahong Jiang、Jinsong Peng、Yuanwei Chen

  DOI：10.1021/ol8002173

  日期：2008.5.1

  A novel route to the synthesis of Delta(2)-isoxazoline derivatives is described. Reaction of beta,gamma-unsaturated oximes with aryl bromides via palladium-catalyzed carboetherification affords 3,5-disubstituted Delta(2)-isoxazolines in good yields. The use of Xantphos as ligand is crucial for the transformation. The carboetherification products can be further converted to beta-hydroxy ketones in the presence of Fe powder and NH(4)Cl.