3-hydroxy-3-methyl-2,5-diphenylpent-4-ynoic acid | 1448604-90-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-hydroxy-3-methyl-2,5-diphenylpent-4-ynoic acid
• 英文别名: 3-Hydroxy-3-methyl-2,5-diphenylpent-4-ynoic acid
• CAS: 1448604-90-7
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: RIGXLVPMHPBHBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  β,β-双(三甲基甲硅烷氧基)苯乙烯 、 4-苯基-3-丁炔-2-酮 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 4.05h， 生成 3-hydroxy-3-methyl-2,5-diphenylpent-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

文献信息

• First direct synthesis of 3-hydroxy-pent-4-ynoic acids. Application to the synthesis of pyran-2-ones
  作者：Morelia E. López-Reyes、José G. López-Cortés、M. Carmen Ortega-Alfaro、R. Alfredo Toscano、Cecilio Alvarez-Toledano

  DOI：10.1016/j.tet.2013.06.069

  日期：2013.9

  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.