hydroxy-2,2-dimethyl-5-phenyl-3-(4-trifluoromethyl)phenyl pent-4-ynoic acid | 1448605-02-4

• 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: hydroxy-2,2-dimethyl-5-phenyl-3-(4-trifluoromethyl)phenyl pent-4-ynoic acid
• CAS: 1448605-02-4
• 化学式: C₂₀H₁₇F₃O₃
• 分子量: 362.348
• InChiKey: XHXUEMIVFDMSAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  双三甲基硅基二甲基烯酮乙醛 、 3-phenyl-1-[4-(trifluoromethyl)phenyl]prop-2-yn-1-one 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 4.05h， 以90%的产率得到hydroxy-2,2-dimethyl-5-phenyl-3-(4-trifluoromethyl)phenyl pent-4-ynoic acid
  参考文献：
  名称：

  First direct synthesis of 3-hydroxy-pent-4-ynoic acids. Application to the synthesis of pyran-2-ones

  摘要：

  We describe a direct method for the synthesis of 3-hydroxy-pent-4-ynoic acids by the nucleophilic addition of bis-(TMS) ketene acetals to alkynones promoted by BF3 center dot Et2O. A systematic study involving electron withdrawing and electron donor groups (R-1=NO2, CF3, Br, Cl, H, Me, OMe) in the propargyl ketone reveals a strong dependence of electronic effects on the regiochemistry of the nucleophilic addition. Using a halolactonization protocol, we demonstrated the synthetic potential of these acids by their efficient transformation into new 5-bromo-3,4-dihydro-2H-pyran-2-ones. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.069