isopropyl (R)-3-hydroxynonanoate | 1253854-94-2

• 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: isopropyl (R)-3-hydroxynonanoate
• 英文别名: i-Propyl (r)-3-hydroxynonanoate；propan-2-yl (3R)-3-hydroxynonanoate
• CAS: 1253854-94-2
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: JRCSLGPCUUBRRL-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-hexyl-oxirane-2-carbaldehyde 、 异丙醇 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 18.25h， 生成 isopropyl (R)-3-hydroxynonanoate
  参考文献：
  名称：

  Organocatalytic Preparation of Simple β-Hydroxy and β-Amino Esters: Low Catalyst Loadings and Gram-Scale Synthesis

  摘要：

  A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence for the synthesis of simple enantioenriched beta-hydroxy and beta-amino esters using commercially available catalysts at low catalyst loadings has been developed. The desired products were obtained in high yield and excellent enantiopurity. The generation of quaternary stereocenters and application in gram-scale synthesis were also realized, with no requirements of inert or anhydrous reaction conditions, thus making this transformation a highly practical protocol.

  DOI：

  10.1021/ol102164y

文献信息

• Organocatalytic Preparation of Simple β-Hydroxy and β-Amino Esters: Low Catalyst Loadings and Gram-Scale Synthesis
  作者：Hao Jiang、Björn Gschwend、Łukasz Albrecht、Karl Anker Jørgensen

  DOI：10.1021/ol102164y

  日期：2010.11.5

  A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence for the synthesis of simple enantioenriched beta-hydroxy and beta-amino esters using commercially available catalysts at low catalyst loadings has been developed. The desired products were obtained in high yield and excellent enantiopurity. The generation of quaternary stereocenters and application in gram-scale synthesis were also realized, with no requirements of inert or anhydrous reaction conditions, thus making this transformation a highly practical protocol.