(2R)-4-methyl-2-phenyl-2H-chromene | 1273578-98-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R)-4-methyl-2-phenyl-2H-chromene
• CAS: 1273578-98-5
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: RQISBZBIFNTPSP-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (2R)-4-methyl-2-phenyl-2H-chromene 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 (2R,4R)-4-methyl-2-phenylchroman 、 (2R,4S)-4-methyl-2-phenyl-3,4-dihydro-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
• 作为产物：
  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