2-phenyl-5-vinyltetrahydrofuran | 59321-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-5-vinyltetrahydrofuran
• 英文别名: trans-2-Vinyl-5-phenyltetrahydrofuran；2-Ethenyl-5-phenyloxolane
• CAS: 59321-60-7
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: JCEUREWUKQCUFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-phenyl-6-trimethylsilanylhex-4-en-1-ol 在 lithium tetrachloropalladate 、 copper dichloride 作用下， 以 异丙醇 为溶剂， 反应 1.5h， 以69%的产率得到2-phenyl-5-vinyltetrahydrofuran
  参考文献：
  名称：

  Umpolung of the reactivity of allylsilanes. Palladium(II) catalyzed cyclization of allylsilyl alcohols: a new route to substituted 2-vinyltetrahydrofurans

  摘要：

  Functionalized allylsilanes 1-4 undergo palladium(II) catalyzed ring closure to afford 4- and/or 5-substituted 2-vinyltetrahydrofurans (5-8) under mild conditions. The catalytic reactions proceed through (eta(3)-allyl)palladium intermediates formed by palladadesilylation of the allylsilane substrates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02245-5

文献信息

• A Mild and Efficient Method for the Stereoselective Formation of C−O Bonds:  Palladium-Catalyzed Allylic Etherification Using Zinc(II) Alkoxides
  作者：Hahn Kim、Chulbom Lee

  DOI：10.1021/ol027104u

  日期：2002.11.1

  [reaction: see text] A highly chemo- and stereoselective palladium-catalyzed allylic etherification reaction is described. The use of zinc(II) alkoxides proved effective in promoting the addition of the oxygen nucleophile derived from aliphatic alcohols to eta(3)-allylpalladium complexes. Using diethylzinc (0.5 equiv), 5 mol % of Pd(OAc)(2), and 7.5 mol % of 2-di(tert-butyl)phosphinobiphenyl in THF

  [反应：见正文]描述了高度化学和立体选择性的钯催化的烯丙基醚化反应。烷氧基锌（II）的使用被证明可有效地促进将脂肪族醇衍生的氧亲核试剂添加到eta（3）-allyallaladium络合物中。使用二乙基锌（0.5当量），5 mol％的Pd（OAc）（2）和7.5 mol％的2-二（叔丁基）膦基联苯在THF中，各种脂肪醇与乙酸烯丙酯之间的交叉偶联反应在在室温下提供具有高立体选择性的烯丙基醚。
• HOSOKAWA T.; SHIMO N.; SONODA A.; MURAHASHI S.-I., HETEROCYCLES, 1975, 3, NO 12, 1145
  作者：HOSOKAWA T.、 SHIMO N.、 SONODA A.、 MURAHASHI S.-I.

  DOI：——

  日期：——
• Umpolung of the reactivity of allylsilanes. Palladium(II) catalyzed cyclization of allylsilyl alcohols: a new route to substituted 2-vinyltetrahydrofurans
  作者：István Macsári、Kálmán J. Szabó

  DOI：10.1016/s0040-4039(99)02245-5

  日期：2000.2

  Functionalized allylsilanes 1-4 undergo palladium(II) catalyzed ring closure to afford 4- and/or 5-substituted 2-vinyltetrahydrofurans (5-8) under mild conditions. The catalytic reactions proceed through (eta(3)-allyl)palladium intermediates formed by palladadesilylation of the allylsilane substrates. (C) 2000 Elsevier Science Ltd. All rights reserved.