7-(phenylethynyl)-3,4-dihydro-2H-[1,5]benzodioxepin | 1187656-80-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(phenylethynyl)-3,4-dihydro-2H-[1,5]benzodioxepin
• 英文别名: 7-(2-phenylethynyl)-3,4-dihydro-2H-1,5-benzodioxepine
• CAS: 1187656-80-9
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: PXUIDRLCWZNRHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙炔 、 7-溴-3,4-二氢-1,5-苯并二噁庚 在 四氢吡咯 、 bis(η3-allyl-μ-chloropalladium(II)) 、 三苯基膦 、 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 反应 4.5h， 以80%的产率得到7-(phenylethynyl)-3,4-dihydro-2H-[1,5]benzodioxepin
  参考文献：
  名称：

  A straightforward copper-free palladium methodology for the selective alkynylation of a wide variety of S-, O-, and N-based mono- and diheterocyclic bromides and chlorides

  摘要：

  High-yield alkynylations are successfully achieved by a simple and widely accessible catalytic system for an unprecedented variety of heterocyclic bromides and chlorides in position -2, -3 or -5: pyridine, quinoline, thiophene, furan, thiazole, benzothiazole, pyrimidine, pyridazine, pyrazine, dioxepin halides are efficiently functionalized in short time reactions. This copper-free methodology employs 1 mol% palladium only, with inexpensive PPh3 and amine base. The ionic liquid solvent allows a straigtforward separation of products and recycling opportunity. Unsuitable substrates and secondary reactions are also reported in order to point out further progress in cross-coupling using ionic liquids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.009

文献信息

• A straightforward copper-free palladium methodology for the selective alkynylation of a wide variety of S-, O-, and N-based mono- and diheterocyclic bromides and chlorides
  作者：Samer Saleh、Michel Picquet、Philippe Meunier、Jean-Cyrille Hierso

  DOI：10.1016/j.tet.2009.06.009

  日期：2009.8

  High-yield alkynylations are successfully achieved by a simple and widely accessible catalytic system for an unprecedented variety of heterocyclic bromides and chlorides in position -2, -3 or -5: pyridine, quinoline, thiophene, furan, thiazole, benzothiazole, pyrimidine, pyridazine, pyrazine, dioxepin halides are efficiently functionalized in short time reactions. This copper-free methodology employs 1 mol% palladium only, with inexpensive PPh3 and amine base. The ionic liquid solvent allows a straigtforward separation of products and recycling opportunity. Unsuitable substrates and secondary reactions are also reported in order to point out further progress in cross-coupling using ionic liquids. (C) 2009 Elsevier Ltd. All rights reserved.