1-bromo-4-((-pent-4-enyloxy)methyl)benzene | 1084847-76-6

• 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: 1-bromo-4-((-pent-4-enyloxy)methyl)benzene
• 英文别名: 1-Bromo-4-(pent-4-enoxymethyl)benzene；1-bromo-4-(pent-4-enoxymethyl)benzene
• CAS: 1084847-76-6
• 化学式: C₁₂H₁₅BrO
• 分子量: 255.155
• InChiKey: ZYCWGAOVKZJGHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  1-bromo-4-((-pent-4-enyloxy)methyl)benzene 在 硼酸三异丙酯 、 叔丁基锂 、 potassium hydrogen difluoride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以75%的产率得到potassium 4((pent-4-enyloxy)methyl)phenyltrifluoroborate
  参考文献：
  名称：

  Orthogonal Reactivity in Boryl-Substituted Organotrifluoroborates

  摘要：

  A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.

  DOI：

  10.1021/ja807076d
• 作为产物：
  描述：

  4-戊烯-1-醇 、 对溴溴苄 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以96%的产率得到1-bromo-4-((-pent-4-enyloxy)methyl)benzene
  参考文献：
  名称：

  Orthogonal Reactivity in Boryl-Substituted Organotrifluoroborates

  摘要：

  A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.

  DOI：

  10.1021/ja807076d

文献信息

• A Hydride Migration Mechanism for the Mo‐Catalyzed <i>Z</i>‐2‐Selective Isomerization of Terminal Alkenes
  作者：Sarah E. Jenny、Juan M. Serviano、Ainara Nova、Graham E. Dobereiner

  DOI：10.1002/cctc.202301052

  日期：2023.12.7

  Selective isomerization of terminal alkenes to Z-2-alkenes is challenging because of the thermodynamic preference for E alkenes. This work investigates the mechanism of a Mo catalyst that achieves high Z selectivity for a range of aliphatic alkenes. DFT analysis points to a hydride migration as key to the isomerization process.

  由于E烯烃的热力学偏好，末端烯烃选择性异构化为 Z - 2 -烯烃具有挑战性。这项工作研究了 Mo 催化剂对一系列脂肪族烯烃实现高Z选择性的机制。DFT 分析指出氢化物迁移是异构化过程的关键。
• Orthogonal Reactivity in Boryl-Substituted Organotrifluoroborates
  作者：Gary A. Molander、Deidre L. Sandrock

  DOI：10.1021/ja807076d

  日期：2008.11.26

  A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.