Methyl 2-(1-naphthalen-1-ylethenyl)benzoate | 1097150-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 2-(1-naphthalen-1-ylethenyl)benzoate
• CAS: 1097150-67-8
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: GBUGWYYJSCMWNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-碘萘 、 2-乙炔苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 三正丁基氢锡 、 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以213 mg的产率得到Methyl 2-(1-naphthalen-1-ylethenyl)benzoate
  参考文献：
  名称：

  Palladium-Catalyzed Markovnikov Terminal Arylalkynes Hydrostannation: Application to the Synthesis of 1,1-Diarylethylenes

  摘要：

  The palladium-catalyzed hydrostannation of terminal arylalkynes was achieved. The regioselectivity of the H-Sn bond addition across the triple bond was found to be controlled by an ortho substituent on the aromatic ring, whatever its electronic nature, to give exclusively alpha-branched vinylstannanes 2 in accordance with Markovnikov's rule. Subsequent Stille cross-coupling reaction of 2 with a variety of aryl halides readily provided, in moderate to good yields, a family of functionalized 1,1-diarylethylenes 1.

  DOI：

  10.1021/jo802460z

文献信息

• Palladium-Catalyzed Markovnikov Terminal Arylalkynes Hydrostannation: Application to the Synthesis of 1,1-Diarylethylenes
  作者：Abdallah Hamze、Damien Veau、Olivier Provot、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1021/jo802460z

  日期：2009.2.6

  The palladium-catalyzed hydrostannation of terminal arylalkynes was achieved. The regioselectivity of the H-Sn bond addition across the triple bond was found to be controlled by an ortho substituent on the aromatic ring, whatever its electronic nature, to give exclusively alpha-branched vinylstannanes 2 in accordance with Markovnikov's rule. Subsequent Stille cross-coupling reaction of 2 with a variety of aryl halides readily provided, in moderate to good yields, a family of functionalized 1,1-diarylethylenes 1.