benzyl pent-3-ynoate | 1187942-38-6

• 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: benzyl pent-3-ynoate
• CAS: 1187942-38-6
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: FJOXWEBIFAJWLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  benzyl pent-3-ynoate 在 silver tetrafluoroborate 、 1,3-双(2,6-二-异丙基苯基)咪唑-2-亚基金(I)氯化物 、 N,N-dimethylphenylammonium trifluoromethanesulfonate 、 potassium hydrogensulfate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 反应 15.08h， 以26%的产率得到
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Fluoroalkenes by Directed Au(I) Catalysis

  摘要：

  Au-catalyzed hydrofluorination reactions of a range of functionalized alkynes are reported. In the presence of an appropriate directing group, localized with particular spacing from the pendant alkyne, regioselective and predictable conversion of the alkyne to the Z-vinyl fluoride may be achieved, In selected cases, yields and selectivities are excellent. Additional experiments with two directing groups installed have established some initial principles with respect to a hierarchy of directing groups and their capacity for influencing hydrofluorination regioselectivity.

  DOI：

  10.1021/ol9016782
• 作为产物：
  描述：

  戊-3-炔酸 、 苯甲醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以59%的产率得到benzyl pent-3-ynoate
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Fluoroalkenes by Directed Au(I) Catalysis

  摘要：

  Au-catalyzed hydrofluorination reactions of a range of functionalized alkynes are reported. In the presence of an appropriate directing group, localized with particular spacing from the pendant alkyne, regioselective and predictable conversion of the alkyne to the Z-vinyl fluoride may be achieved, In selected cases, yields and selectivities are excellent. Additional experiments with two directing groups installed have established some initial principles with respect to a hierarchy of directing groups and their capacity for influencing hydrofluorination regioselectivity.

  DOI：

  10.1021/ol9016782

文献信息

• Selective Catalytic Cross‐Cyclotrimerization En Route to1,4‐Diborylated Benzenes and Their Synthetic Transformations
  作者：Alexander A. Fadeev、Gabriele Manca、Martin Kotora

  DOI：10.1002/adsc.202201337

  日期：——

  available ethynyl boronate. The reaction is applicable to a wide array of alkynes with metal-coordinating groups, providing synthetically useful diborylated benzenes in 23–68% isolated yields. DFT calculations shed light on the reaction course and the origin of its remarkable regioselectivity. Selected diborylated benzenes were converted into various products, such as quinones and hydroquinones, including

  1,4-二硼酸化苯的合成是通过 Ru 催化的炔烃与市售硼酸乙炔酯的区域选择性共环三聚反应实现的。该反应适用于具有金属配位基团的各种炔烃，以 23-68% 的分离产率提供合成有用的二硼基化苯。DFT 计算揭示了反应过程及其显着区域选择性的起源。选定的二硼化苯被转化为各种产品，如醌和氢醌，包括三种天然生物活性小分子。