(E)-2-(2-hydroxy-4-phenylbut-3-en-2-yl)phenol | 1273578-83-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-(2-hydroxy-4-phenylbut-3-en-2-yl)phenol
• 英文别名: 2-[(E)-2-hydroxy-4-phenylbut-3-en-2-yl]phenol
• CAS: 1273578-83-8
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: GTXLGFWKWJTMNK-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-hydroxy-4-phenylbut-3-en-2-yl)phenol 在 C₂₅H₁₇F₃NO₅PS 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以92%的产率得到(2R)-4-methyl-2-phenyl-2H-chromene
  参考文献：
  名称：

  Chiral Organic Contact Ion Pairs in Metal-Free Catalytic Asymmetric Allylic Substitutions

  摘要：

  Chiral contact ion-pair catalysis with particular focus on metal-free processes is gaining in interest. As a result, new perspectives are opened, and highly stereoselective transformations, traditionally performed under metal catalysis, can be realized. Herein, we report the development of an unprecedented asymmetric Bronsted acid-catalyzed allylic alkylation. The concept relies on chiral contact ion-pair catalysis, in which the chiral organic counteranion of an allylic carbocation induces high enantioselectivities and allows access to biologically relevant chromenes in good yields and with excellent enantioselection.

  DOI：

  10.1021/ja110213t

文献信息

• Boronic Acid Catalysis as a Mild and Versatile Strategy for Direct Carbo- and Heterocyclizations of Free Allylic Alcohols
  作者：Hongchao Zheng、Sina Ghanbari、Shinji Nakamura、Dennis G. Hall

  DOI：10.1002/anie.201201620

  日期：2012.6.18

  BAC to the future: Boronic acid catalysis (BAC) was applied to the direct activation of alcohols leading to the preparation of carbocycles (see scheme), benzofurans, tetrahydrofurans, pyrrolidines, pyrans, piperidines, and various polycyclic compounds. The reactions proceed under mild conditions that circumvent the use of reactive leaving groups like halides.

  未来的BAC：将硼酸催化（BAC）应用于醇的直接活化，从而制备碳环（参见方案），苯并呋喃，四氢呋喃，吡咯烷，吡喃，哌啶和各种多环化合物。反应在避开反应性离去基团（如卤化物）的温和条件下进行。