(2S,4S,5R)-2-[(1R,2S,5R)-8-phenylmenthoxy]-3,4-dimethyl-5-phnyl-1,3,2-oxazaphospholidin-2-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,4S,5R)-2-[(1R,2S,5R)-8-phenylmenthoxy]-3,4-dimethyl-5-phnyl-1,3,2-oxazaphospholidin-2-one
• 化学式: C₂₆H₃₆NO₃P
• 分子量: 441.551
• InChiKey: XYZSAFAFGNHJKK-LIXMQVCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  盐酸麻黄碱 、 alkaline earth salt of/the/ methylsulfuric acid 在 甲基氯化镁 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (2S,4S,5R)-2-[(1R,2S,5R)-8-phenylmenthoxy]-3,4-dimethyl-5-phnyl-1,3,2-oxazaphospholidin-2-one
  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.