3-(trimethylstannyl)-5-bromo-2-pyrone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(trimethylstannyl)-5-bromo-2-pyrone
• 英文别名: 5-Bromo-3-trimethylstannylpyran-2-one
• 化学式: C₈H₁₁BrO₂Sn
• 分子量: 337.788
• InChiKey: NZDDDHSCNLHFCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-硝基碘苯 、 3-(trimethylstannyl)-5-bromo-2-pyrone 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以64%的产率得到3-(2-nitrophenyl)-5-bromo-2-pyrone
  参考文献：
  名称：

  Stille couplings of 3-(trimethylstannyl)-5-bromo-2-pyrone for the syntheses of 3-aryl-5-bromo-2-pyrones and their ambident dienyl characters

  摘要：

  3-(Trimethylstannyl)-5-bromo-2-pyrone underwent facile Stille Coupling reactions with aryl halides to produce various 3-substituted 5-bromo-2-pyrones. The resulting 3-aryl-2-pyrone derivatives underwent both normal and inverse electron demand Diels Alder cycloadditions depending on the type of the dienophiles being reacted. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01182-6

文献信息

• Efficient and selective Stille cross-coupling of benzylic and allylic bromides using bromobis(triphenylphosphine)(N-succinimide)palladium(II)
  作者：Catherine M. Crawforth、Ian J.S. Fairlamb、Richard J.K. Taylor

  DOI：10.1016/j.tetlet.2003.11.014

  日期：2004.1

  [Pd(NCOC2H4CO)(PPh3)2Br] 1. Significantly, these reactions do not require the use of hexamethylphosphoramide (HMPA) as the solvent, or additional ligands, such as trifurylphosphine or triphenylarsine. Selectivity for benzyl bromide over bromobenzene is observed for precatalyst 1, against the precatalysts, bromobis(triphenylphosphine)(benzyl)palladium(II) and bis(triphenylphosphine)palladium(II) bromide.

  使用预催化剂[Pd（NCOC 2 H 4 CO）（PPh 3）2 Br] 1可以使烯丙基和苄基溴与有机锡烷交联。重要的是，这些反应不需要使用六甲基磷酰胺（HMPA）作为溶剂，也不需要使用其他配体，例如三糠基膦或三苯基ar。对于预催化剂1，观察到苄基溴对溴苯的选择性相对于预催化剂溴双（三苯基膦）（苄基）钯（II）和双（三苯基膦）钯（II）。
• Stille couplings of 3-(trimethylstannyl)-5-bromo-2-pyrone for the syntheses of 3-aryl-5-bromo-2-pyrones and their ambident dienyl characters
  作者：Jin-Hee Lee、Won-Suk Kim、Young Yiol Lee、Cheon-Gyu Cho

  DOI：10.1016/s0040-4039(02)01182-6

  日期：2002.8

  3-(Trimethylstannyl)-5-bromo-2-pyrone underwent facile Stille Coupling reactions with aryl halides to produce various 3-substituted 5-bromo-2-pyrones. The resulting 3-aryl-2-pyrone derivatives underwent both normal and inverse electron demand Diels Alder cycloadditions depending on the type of the dienophiles being reacted. (C) 2002 Elsevier Science Ltd. All rights reserved.