(R)-4-[(Z)-benzylidene]-2-n-butoxytetrahydrofuran | 1141884-93-6

• 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: (R)-4-[(Z)-benzylidene]-2-n-butoxytetrahydrofuran
• 英文别名: (2R,4Z)-4-benzylidene-2-butoxyoxolane
• CAS: 1141884-93-6
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: RFQZMMDJXUCVNI-BAAYTWLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  乙烯基正丁醚 、 3-苯基丙-2-烯-1-醇 在 氧气 、 copper diacetate 、 palladium diacetate 、 邻苯二酚 、 2,2′-双[(4S)-4-苄基-2-噁唑啉] 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 (R)-4-[(Z)-benzylidene]-2-n-butoxytetrahydrofuran 、 (S)-4-[(Z)-benzylidene]-2-n-butoxytetrahydrofuran
  参考文献：
  名称：

  Palladium(II)-Catalyzed Asymmetric Coupling of Allylic Alcohols and Vinyl Ethers: Insight into the Palladium and Copper Bimetallic Catalyst

  摘要：

  [GRAPHICS]The use of PdX2, CuX2 (X = OAc, OCOCF3, or Cl), and catechol together with (S,S)-4,4'-bisbenzyl-2,2'-bioxazoline under O-2 induces the asymmetric coupling of cinnamyl alcohols and vinyl ethers to give (R)-(+)-2-alkoxy-4-benzylidenetetrahydrofurans in 40-53% ee (79% yield). The present study provides implications for the so-called Wacker catalyst of PdX2 and CuX2, in terms of that the anionic ligands (X) of Pd and Cu interchange between two metals.

  DOI：

  10.1021/jo802807w

文献信息

• Palladium(II)-Catalyzed Asymmetric Coupling of Allylic Alcohols and Vinyl Ethers: Insight into the Palladium and Copper Bimetallic Catalyst
  作者：Yasufumi Kawamura、Yasuhiro Kawano、Tomohiro Matsuda、Yûta Ishitobi、Takahiro Hosokawa

  DOI：10.1021/jo802807w

  日期：2009.4.17

  [GRAPHICS]The use of PdX2, CuX2 (X = OAc, OCOCF3, or Cl), and catechol together with (S,S)-4,4'-bisbenzyl-2,2'-bioxazoline under O-2 induces the asymmetric coupling of cinnamyl alcohols and vinyl ethers to give (R)-(+)-2-alkoxy-4-benzylidenetetrahydrofurans in 40-53% ee (79% yield). The present study provides implications for the so-called Wacker catalyst of PdX2 and CuX2, in terms of that the anionic ligands (X) of Pd and Cu interchange between two metals.