3-methyl-2-styrylbenzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-methyl-2-styrylbenzofuran
• 英文别名: 3-methyl-2-[(E)-2-phenylethenyl]-1-benzofuran
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: HKNITJVGCHEAFZ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-碘-2-(2-丙炔氧基)苯 在 palladium diacetate potassium tert-butylate 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 17.5h， 生成 3-methyl-2-styrylbenzofuran
  参考文献：
  名称：

  Palladium catalysed tandem cyclisation-anion capture processes. Part 3. Organoboron anion transfer agents

  摘要：

  The cyclisation-anion capture protocol has been applied to a wide range of starter and terminating species to effect regio-and stereo-specific mono-and bis-cyclisation processes in which a variety of organoboronderivatives function as anion transfer reagents. Direct capture (no cyclisation) is rarely a problem and it can usually be suppressed by modification of the reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00754-0

文献信息

• Development of a Decarboxylative Palladation Reaction and Its Use in a Heck-type Olefination of Arene Carboxylates
  作者：Andrew G. Myers、Daisuke Tanaka、Michael R. Mannion

  DOI：10.1021/ja027523m

  日期：2002.9.1

  The development of a palladium-catalyzed decarboxylative coupling reaction of arene carboxylates with olefinic substrates is described. The optimized procedure for decarboxylative palladation employs Pd(O2CCF3)2 as catalyst (0.2 equiv) in the presence of Ag2CO3 (3 equiv) in the solvent 5% DMSO-DMF and proceeds at temperatures of 80-120 degrees C with a wide range of arene carboxylates and alkenes as substrates. The process is proposed to proceed by an initial Ar-SE reaction involving ipso attack of an electrophilic Pd(II) intermediate on an arene carboxylate to form an arylpalladium(II) species with loss of carbon dioxide. This intermediate is then proposed to react with an olefinic substrate by steps common to the Heck coupling process. Reoxidation of the liberated Pd(0) in situ is proposed to establish the catalytic cycle.
• Palladium catalysed tandem cyclisation-anion capture processes. Part 3. Organoboron anion transfer agents
  作者：Ronald Grigg、JoséM. Sansano、Vijayaratnam Santhakumar、Visuvanathar Sridharan、Ravishanker Thangavelanthum、Mark Thornton-Pett、David Wilson

  DOI：10.1016/s0040-4020(97)00754-0

  日期：1997.8

  The cyclisation-anion capture protocol has been applied to a wide range of starter and terminating species to effect regio-and stereo-specific mono-and bis-cyclisation processes in which a variety of organoboronderivatives function as anion transfer reagents. Direct capture (no cyclisation) is rarely a problem and it can usually be suppressed by modification of the reaction conditions. (C) 1997 Elsevier Science Ltd.