2,2,4-trimethyl-5-phenyloxazolidine | 532429-46-2

• 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: 2,2,4-trimethyl-5-phenyloxazolidine
• 英文别名: (4S,5R)-2,2,4-trimethyl-5-phenyl-1,3-oxazolidine
• CAS: 532429-46-2
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: GSJWOQQDBDJRHN-ONGXEEELSA-N

物化性质

• 沸点：
  278.3±28.0 °C(Predicted)
• 密度：
  0.964±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,4-trimethyl-5-phenyloxazolidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到(1R,2S)-2-(isopropylamino)-1-phenyl-1-propanol
  参考文献：
  名称：

  Preparation of Chiral Phosphorus(V) Reagents and Their Uses with Borane in the Enantioselective Reduction of Ketones

  摘要：

  AbstractChiral pentavalent phosphorus reagents 5–17 were prepared from POCl3 and ephedrine (or the related α‐amino alcohols), followed by substitution with nucleophiles of phenylmagnesium bromide, alcohols, amines, diamines and triamines. The substitution reactions occurred in a stereospecific manner with retention of the configuration at the phosphorus center. The structures of these phosphorus(V) reagents were determined by spectral methods and verified by X‐ray diffraction in several instances. These phosphorus(V) reagents were used with borane/dimethylsulfide complex in the enantioselective reduction of aromatic, aliphatic and heterocyclic ketones. The phosphorus(V) reagents likely functioned as Lewis bases to react with borane, forming in situ zwitterionic species as the chiral reducing agents. The reactions were generally carried out at 0 °C in tetrahydrofuran solution with a molar ratio of ketone/borane/phosphoramidate = 1:1:0.2 to afford secondary alcohols with modest enantioselectivity, up to 67% ee in the reduction of 4′‐methylacetophenone.

  DOI：

  10.1002/jccs.199900108
• 作为产物：
  描述：

  去甲麻黄碱 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 2,2,4-trimethyl-5-phenyloxazolidine
  参考文献：
  名称：

  Preparation of Chiral Phosphorus(V) Reagents and Their Uses with Borane in the Enantioselective Reduction of Ketones

  摘要：

  AbstractChiral pentavalent phosphorus reagents 5–17 were prepared from POCl3 and ephedrine (or the related α‐amino alcohols), followed by substitution with nucleophiles of phenylmagnesium bromide, alcohols, amines, diamines and triamines. The substitution reactions occurred in a stereospecific manner with retention of the configuration at the phosphorus center. The structures of these phosphorus(V) reagents were determined by spectral methods and verified by X‐ray diffraction in several instances. These phosphorus(V) reagents were used with borane/dimethylsulfide complex in the enantioselective reduction of aromatic, aliphatic and heterocyclic ketones. The phosphorus(V) reagents likely functioned as Lewis bases to react with borane, forming in situ zwitterionic species as the chiral reducing agents. The reactions were generally carried out at 0 °C in tetrahydrofuran solution with a molar ratio of ketone/borane/phosphoramidate = 1:1:0.2 to afford secondary alcohols with modest enantioselectivity, up to 67% ee in the reduction of 4′‐methylacetophenone.

  DOI：

  10.1002/jccs.199900108

文献信息

• Preparation of Chiral Phosphorus(V) Reagents and Their Uses with Borane in the Enantioselective Reduction of Ketones
  作者：Guo-Hsian Chen、Jue-Liang Hsu、Wen-Bin Yang、Jim-Min Fang、Gene-Hsiang Lee、Yi-Hung Liu、Yu Wang

  DOI：10.1002/jccs.199900108

  日期：1999.10

  AbstractChiral pentavalent phosphorus reagents 5–17 were prepared from POCl3 and ephedrine (or the related α‐amino alcohols), followed by substitution with nucleophiles of phenylmagnesium bromide, alcohols, amines, diamines and triamines. The substitution reactions occurred in a stereospecific manner with retention of the configuration at the phosphorus center. The structures of these phosphorus(V) reagents were determined by spectral methods and verified by X‐ray diffraction in several instances. These phosphorus(V) reagents were used with borane/dimethylsulfide complex in the enantioselective reduction of aromatic, aliphatic and heterocyclic ketones. The phosphorus(V) reagents likely functioned as Lewis bases to react with borane, forming in situ zwitterionic species as the chiral reducing agents. The reactions were generally carried out at 0 °C in tetrahydrofuran solution with a molar ratio of ketone/borane/phosphoramidate = 1:1:0.2 to afford secondary alcohols with modest enantioselectivity, up to 67% ee in the reduction of 4′‐methylacetophenone.