3-hydroxy-2,2,3-trimethyl-5-(trimethylsilyl)pent-4-ynoic acid | 1448604-95-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-hydroxy-2,2,3-trimethyl-5-(trimethylsilyl)pent-4-ynoic acid
• 英文别名: 3-Hydroxy-2,2,3-trimethyl-5-trimethylsilylpent-4-ynoic acid；3-hydroxy-2,2,3-trimethyl-5-trimethylsilylpent-4-ynoic acid
• CAS: 1448604-95-2
• 化学式: C₁₁H₂₀O₃Si
• 分子量: 228.363
• InChiKey: GUNDXMPBMPENEM-UHFFFAOYSA-N

物化性质

• 沸点：
  319.2±32.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  双三甲基硅基二甲基烯酮乙醛 、 4-三甲基硅基-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， 以98%的产率得到3-hydroxy-2,2,3-trimethyl-5-(trimethylsilyl)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

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.