2-(trineophylstannyl)-1-phenyl-2-propen-1-one | 648425-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(trineophylstannyl)-1-phenyl-2-propen-1-one
• 英文别名: 2-Propen-1-one, 1-phenyl-2-[tris(2-methyl-2-phenylpropyl)stannyl]-；1-phenyl-2-tris(2-methyl-2-phenylpropyl)stannylprop-2-en-1-one
• CAS: 648425-07-4
• 化学式: C₃₉H₄₆OSn
• 分子量: 649.504
• InChiKey: XEDUCKDZEALOLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.35
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(trineophylstannyl)-1-phenyl-2-propen-1-one 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到2-iodo-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  Stereoselective Synthesis of Stannyl Enones via Palladium-Catalyzed and Free Radical Hydrostannation of Alkynyl Ketones with Trineophyltin Hydride

  摘要：

  A study on the addition of trineophyltin hydride (1) to alkynones under free radical (AIBN and Et3B) and palladium-catalyzed [(PPh3)(2)PdCl2] conditions is reported. The results obtained indicate that the addition of 1 to eight ynones catalyzed by bis(triphenylphosphine)palladium(II) chloride led in all cases to addition products in very high yields (80-96%). These additions take place with excellent regio- and stereochemistry, leading to the alpha adducts as major products in seven out of the eight cases studied. Also the E adducts, resulting from a syn attack, were the only (seven cases) or the predominant (one case) products. The radical hydrostannations initiated by AIBN of ynones 2-5 with 1 led to addition products in good yields (60-88%); with the more hindered ketones 6 and 7-9 the yields obtained were lower. The radical additions initiated by triethylboron to ynones 2-6 follow a similar pattern but with lower yields; no addition products in the hydrostannation of ynones 7-9 were detected. The new acyl-substituted vinylstannanes, owing to their greater stability compared with that of their tributyl- and trimethylstannyl analogues, can be purified by column chromatography using neutral alumina (in all cases) or silica gel 60 (in most cases) as adsorbents. Full H-1, C-13, and Sn-119 NMR data are given.

  DOI：

  10.1021/jo035396m

文献信息

• Stereoselective Synthesis of Stannyl Enones via Palladium-Catalyzed and Free Radical Hydrostannation of Alkynyl Ketones with Trineophyltin Hydride
  作者：Verónica I. Dodero、Liliana C. Koll、M. Belén Faraoni、Terence N. Mitchell、Julio C. Podestá

  DOI：10.1021/jo035396m

  日期：2003.12.1

  A study on the addition of trineophyltin hydride (1) to alkynones under free radical (AIBN and Et3B) and palladium-catalyzed [(PPh3)(2)PdCl2] conditions is reported. The results obtained indicate that the addition of 1 to eight ynones catalyzed by bis(triphenylphosphine)palladium(II) chloride led in all cases to addition products in very high yields (80-96%). These additions take place with excellent regio- and stereochemistry, leading to the alpha adducts as major products in seven out of the eight cases studied. Also the E adducts, resulting from a syn attack, were the only (seven cases) or the predominant (one case) products. The radical hydrostannations initiated by AIBN of ynones 2-5 with 1 led to addition products in good yields (60-88%); with the more hindered ketones 6 and 7-9 the yields obtained were lower. The radical additions initiated by triethylboron to ynones 2-6 follow a similar pattern but with lower yields; no addition products in the hydrostannation of ynones 7-9 were detected. The new acyl-substituted vinylstannanes, owing to their greater stability compared with that of their tributyl- and trimethylstannyl analogues, can be purified by column chromatography using neutral alumina (in all cases) or silica gel 60 (in most cases) as adsorbents. Full H-1, C-13, and Sn-119 NMR data are given.