2-hydroxy-2-isopropyl-pent-4-enoic acid

• 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: 2-hydroxy-2-isopropyl-pent-4-enoic acid
• 英文别名: α-Oxy-α-allyl-isovaleriansaeure；3-Oxy-2-methyl-hexen-(5)-carbonsaeure-(3)；2-Hydroxy-2-isopropyl-pent-4-ensaeure；2-Hydroxy-2-propan-2-ylpent-4-enoic acid
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: JETJXWASPMKZMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  丙烯基三氯硅烷 、 2-氧代-3-甲基丁酸 在 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以73%的产率得到2-hydroxy-2-isopropyl-pent-4-enoic acid
  参考文献：
  名称：

  Chemoselective allylic addition of allyltrichlorosilane to α-oxocarboxylic acids: synthesis of tertiary α-hydroxy carboxylic acids

  摘要：

  Allyltrichlorosilane can add to alpha-oxocarboxylic acids in the presence of DMF and HMPA. The alpha-carboxylic substituent exerts a remarkable neighboring group effect on the reaction, The reaction presumably proceeds in an intramolecular fashion through a 'rigid' bicyclic transition state assembly involving a hypervalent silicate species, which produces the chemoselectivity approaching 100%. (C) 2000 Dupont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00692-4

文献信息

• Chemoselective allylic addition of allyltrichlorosilane to α-oxocarboxylic acids: synthesis of tertiary α-hydroxy carboxylic acids
  作者：Zhe Wang、Guoyou Xu、Dengjin Wang、Michael E. Pierce、Pat N. Confalone

  DOI：10.1016/s0040-4039(00)00692-4

  日期：2000.6

  Allyltrichlorosilane can add to alpha-oxocarboxylic acids in the presence of DMF and HMPA. The alpha-carboxylic substituent exerts a remarkable neighboring group effect on the reaction, The reaction presumably proceeds in an intramolecular fashion through a 'rigid' bicyclic transition state assembly involving a hypervalent silicate species, which produces the chemoselectivity approaching 100%. (C) 2000 Dupont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.