(R)-2-hydroxy-2-phenyl-N,N-dimethylacetamide | 97315-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-hydroxy-2-phenyl-N,N-dimethylacetamide
• 英文别名: (R)-2-hydroxy-N,N-dimethyl-2-phenylacetamide；D-mandelic acid-dimethylamide；D-Mandelsaeure-dimethylamid；(R)-2-Hydroxy-N,N-dimethyl-2-phenylacetamide；(2R)-2-hydroxy-N,N-dimethyl-2-phenylacetamide
• CAS: 97315-03-2
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: RAPXOLIRIJRICD-SECBINFHSA-N

物化性质

• 沸点：
  321.6±35.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-hydroxy-2-phenyl-N,N-dimethylacetamide 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 mineral oil 为溶剂， 生成 (R)-2-methoxy-N,N-dimethyl-2-phenylethanamine
  参考文献：
  名称：

  Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation

  摘要：

  A new class of chiral 1,2-amino ether ligands, readily accessible from naturally occurring alpha-amino- or alpha-hydroxy acids, was found to provide high levels of both conversion and stereocontrol (up to 95:5 er) in intramolecular carbolithiation reactions, outperforming the benchmark ligand (-)-sparteine. The ligand could, be used in a substoichiometric amount (0.25 equiv) without significant loss of enantios electivity.

  DOI：

  10.1021/acs.joc.7b00423
• 作为产物：
  描述：

  (S)-2-hydroxy-2-phenyl-N,N-dimethylacetamide 生成 (R)-2-hydroxy-2-phenyl-N,N-dimethylacetamide
  参考文献：
  名称：

  Cesium carboxylates in dimethyl formamide. Reagents for introduction of hydroxyl groups by nucleophilic substitution and for inversion of configuration of secondary alcohols

  摘要：

  DOI：

  10.1021/jo00334a055

文献信息

• Freudenberg; Todd; Seidler, Justus Liebigs Annalen der Chemie, 1933, vol. 501, p. 208
  作者：Freudenberg、Todd、Seidler

  DOI：——

  日期：——
• Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation
  作者：Hélène Guyon、Anne Boussonnière、Anne-Sophie Castanet

  DOI：10.1021/acs.joc.7b00423

  日期：2017.5.5

  A new class of chiral 1,2-amino ether ligands, readily accessible from naturally occurring alpha-amino- or alpha-hydroxy acids, was found to provide high levels of both conversion and stereocontrol (up to 95:5 er) in intramolecular carbolithiation reactions, outperforming the benchmark ligand (-)-sparteine. The ligand could, be used in a substoichiometric amount (0.25 equiv) without significant loss of enantios electivity.
• Cesium carboxylates in dimethyl formamide. Reagents for introduction of hydroxyl groups by nucleophilic substitution and for inversion of configuration of secondary alcohols
  作者：Wim H. Kruizinga、Bert Strijtveen、Richard M. Kellogg

  DOI：10.1021/jo00334a055

  日期：1981.10