(E)-2-(3-phenoxy-1-propen-1-yl)thiophene | 1351287-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2-(3-phenoxy-1-propen-1-yl)thiophene
• 英文别名: (E)-2-(3-phenoxyprop-1-en-1-yl)thiophene；2-[(E)-3-phenoxyprop-1-enyl]thiophene
• CAS: 1351287-71-2
• 化学式: C₁₃H₁₂OS
• 分子量: 216.304
• InChiKey: CXCRJWCEZRHLBT-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯酚 在 potassium phosphate 、 dichloro(cycloocta-1,5-diene)palladium (II) 、 四丁基溴化铵 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 28.0h， 生成 (E)-2-(3-phenoxy-1-propen-1-yl)thiophene
  参考文献：
  名称：

  从芳族卤化物，酚和烯丙基氯化物高效钯催化合成肉桂醚

  摘要：

  AbstractA one‐pot, two‐step catalytic protocol for the preparation of cinnamyl ethers from simple and readily available aryl halides, phenols and allyl chloride is reported for the first time. This simple and highly efficient palladium nanoparticles catalytic system shows good regio‐ and stereoselectivities and affords the desired products in good to high yields (49–85%) from aryl iodides. Furthermore, less reactive aryl bromides can also give the cinnamyl ethers in moderate yields (24–72%).magnified image

  DOI：

  10.1002/adsc.201300757

文献信息

• Pd-Catalyzed Olefination of Furans and Thiophenes with Allyl Esters
  作者：Yuexia Zhang、Zejiang Li、Zhong-Quan Liu

  DOI：10.1021/ol203013p

  日期：2012.1.6

  A direct Pd(II)-catalyzed olefination of furans and thiophenes with allyl esters is demonstrated. Under the typical conditions, the dehydrogenative Heck coupling reactions of heteroarenes with allylic esters proceeded via a β-H elimination rather than a β-OAc elimination to give the corresponding γ-substituted allylic esters.

  证明了呋喃和噻吩与烯丙基酯的直接Pd（II）催化的烯化反应。在典型条件下，杂芳烃与烯丙基酯的脱氢Heck偶联反应通过β-H消除而不是β-OAc消除进行，得到相应的γ-取代的烯丙基酯。
• An Efficient Palladium-Catalyzed Synthesis of Cinnamyl Ethers from Aromatic Halides, Phenols, and Allylic Chloride
  作者：Wei Wang、Rong Zhou、Zhi-Jie Jiang、Kun Wang、Hai-Yan Fu、Xue-Li Zheng、Hua Chen、Rui-Xiang Li

  DOI：10.1002/adsc.201300757

  日期：2014.2.10

  AbstractA one‐pot, two‐step catalytic protocol for the preparation of cinnamyl ethers from simple and readily available aryl halides, phenols and allyl chloride is reported for the first time. This simple and highly efficient palladium nanoparticles catalytic system shows good regio‐ and stereoselectivities and affords the desired products in good to high yields (49–85%) from aryl iodides. Furthermore, less reactive aryl bromides can also give the cinnamyl ethers in moderate yields (24–72%).magnified image