(4R,5R)-4,5-bis(2-(cyclohept-1-enyl)-4-fluorophenyl)-2,2-dimethyl-1,3-dioxolane | 1191072-39-5

• 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: (4R,5R)-4,5-bis(2-(cyclohept-1-enyl)-4-fluorophenyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 1191072-39-5
• 化学式: C₃₁H₃₆F₂O₂
• 分子量: 478.622
• InChiKey: ZAKCSZDKMPDECM-LOYHVIPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.23
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4,5-bis(2-(cyclohept-1-enyl)-4-fluorophenyl)-2,2-dimethyl-1,3-dioxolane 在 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以78%的产率得到(R,R)-1,2-bis(2-(cyclohept-1-enyl)-4-fluorophenyl)ethane-1,2-diol
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology

  摘要：

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.

  DOI：

  10.1021/ja906429c
• 作为产物：
  描述：

  (4R,5R)-4,5-bis(2-bromo-4-fluorophenyl)-2,2-dimethyl-1,3-dioxolane 、 1-环庚烯-1-硼酸频哪醇酯 在 potassium phosphate 、 水 、 palladium diacetate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以92%的产率得到(4R,5R)-4,5-bis(2-(cyclohept-1-enyl)-4-fluorophenyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology

  摘要：

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.

  DOI：

  10.1021/ja906429c