5-(4-acetophenyl)-2,3-dihydrohuran

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-acetophenyl)-2,3-dihydrohuran
• 英文别名: 1-[4-(2,3-Dihydrofuran-5-yl)phenyl]ethanone
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: LCGMGTSBYILGCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-碘代苯乙酮 、 2,3-Dihydrofuran-5-yl-di(propan-2-yl)silane 在 四丁基氢氧化铵 、 bis(η3-allyl-μ-chloropalladium(II)) 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 0.17h， 以71%的产率得到5-(4-acetophenyl)-2,3-dihydrohuran
  参考文献：
  名称：

  Mild and General Cross-Coupling of (α-Alkoxyvinyl)silanols and -silyl Hydrides

  摘要：

  [GRAPHICS](alpha-Alkoxyvinyl)silanols and (alpha-alkoxyvinyl)silyl hydrides are efficiently converted to aryl vinyl ethers by a palladium(0)-catalyzed cross-coupling reaction with aryl halides in the presence of tetrabutylammonium fluoride or hydroxide. Yields are generally high, and the reaction is compatible with a wide range of functional groups.

  DOI：

  10.1021/ol0064112

文献信息

• Oxime-Derived Palladium Complexes as Very Efficient Catalysts for the Heck–Mizoroki Reaction
  作者：Diego A. Alonso、Carmen Nájera、Ma Carmen Pacheco

  DOI：10.1002/1615-4169(200202)344:2<172::aid-adsc172>3.0.co;2-9

  日期：2002.2

  Oxime-derived, chloro-bridged palladacycles 16 are efficient complexes for the Heck vinylation of aryl halides. The isolated catalysts are thermally stable, not sensitive to air or moisture and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions, with aryl iodides, bromides and chlorides with acrylic esters and olefins displaying turnover numbers (TON) of up to 10(10) for phenyl iodide and turnover frequencies (TOF) of 1.4 x 10(8) h(-1). Deactivated aryl bromides undergo the Heck reaction with styrene with TON and TOF values up to 97,000 and 6063 h-1, respectively. Even aryl chlorides undergo the coupling reaction with olefins with TON up to 920. Complexes 16 catalyze the synthesis of 2,3-disubstituted indenones and indoles in good yields via annulation reaction of internal alkynes with o-bromo- or o-chlorobenzaldehyde and o-iodoaniline, respectively.
• Mild and General Cross-Coupling of (α-Alkoxyvinyl)silanols and -silyl Hydrides
  作者：Scott E. Denmark、Luc Neuville

  DOI：10.1021/ol0064112

  日期：2000.10.1

  [GRAPHICS](alpha-Alkoxyvinyl)silanols and (alpha-alkoxyvinyl)silyl hydrides are efficiently converted to aryl vinyl ethers by a palladium(0)-catalyzed cross-coupling reaction with aryl halides in the presence of tetrabutylammonium fluoride or hydroxide. Yields are generally high, and the reaction is compatible with a wide range of functional groups.