4-(4-methoxyphenyl)but-3-en-1-yl acetate | 1266606-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)but-3-en-1-yl acetate
• CAS: 1266606-64-7
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: BGRRGEBWXWHZLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)but-3-en-1-yl acetate 、 乙酸酐 在 α,α,α-三联吡啶 、 氧气 、 palladium diacetate 、 溶剂黄146 、 联硼酸频那醇酯 作用下， 以 乙腈 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 以20%的产率得到
  参考文献：
  名称：

  B₂pin₂-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O₂ as Oxygen Source and Sole Oxidant

  摘要：

  A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.

  DOI：

  10.1021/acs.orglett.8b01806
• 作为产物：
  描述：

  乙酸 -3-丁烯酯 、 碘苯二乙酸 、 三丁基(4-甲氧基苯基)锡 在 二(氰基苯)二氯化钯 作用下， 以 甲苯 为溶剂， 以62%的产率得到1-(4-methoxyphenyl)butane-1,4-diyl diacetate
  参考文献：
  名称：

  钯催化的末端烯烃的 1,1-芳基氧化

  摘要：

  本文描述了使用有机锡烷和高价碘氧化剂对多种 α-烯烃进行 1,1-芳基乙酰氧基化。该反应为在单个催化转化中生成 C−C 和 C−O 键以及新的立体中心提供了一种收敛方法。

  DOI：

  10.1021/ol103121r

文献信息

• B₂pin₂-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O₂ as Oxygen Source and Sole Oxidant
  作者：Jiuzhong Huang、Lu Ouyang、Jianxiao Li、Jia Zheng、Wuxin Yan、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.8b01806

  日期：2018.9.7

  A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.
• Palladium-Catalyzed 1,1-Aryloxygenation of Terminal Olefins
  作者：Andrew D. Satterfield、Asako Kubota、Melanie S. Sanford

  DOI：10.1021/ol103121r

  日期：2011.3.4

  This paper describes the 1,1-arylacetoxylation of diverse α-olefins using organostannanes and hypervalent iodine oxidants. The reaction provides a convergent approach for generating a C−C and a C−O bond as well as a new stereocenter in a single catalytic transformation.

  本文描述了使用有机锡烷和高价碘氧化剂对多种 α-烯烃进行 1,1-芳基乙酰氧基化。该反应为在单个催化转化中生成 C−C 和 C−O 键以及新的立体中心提供了一种收敛方法。