3-hydroxy-2,2,3-trimethyl-5-phenylpentanoic acid | 1376112-78-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 3-hydroxy-2,2,3-trimethyl-5-phenylpentanoic acid
• CAS: 1376112-78-5
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: KFDXZUSYIHCOQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2,2,3-trimethyl-5-phenylpentanoic acid 在 4-二甲氨基吡啶 、 2-甲基-6-硝基苯甲酸酐 、 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 以95%的产率得到4-(2-phenylethyl)-3,3,4-trimethyloxetan-2-one
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r
• 作为产物：
  描述：

  苄基丙酮 、 异丁酸 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以70%的产率得到3-hydroxy-2,2,3-trimethyl-5-phenylpentanoic acid
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r

文献信息

• MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin
  作者：Isamu Shiina、Yuma Umezaki、Nobutaka Kuroda、Takashi Iizumi、Shunsuke Nagai、Takashi Katoh

  DOI：10.1021/jo300139r

  日期：2012.6.1

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.