(2S,4S,5R)-3,4-Dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine 2-oxide | 54655-12-8

• 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: (2S,4S,5R)-3,4-Dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine 2-oxide
• 英文别名: (2S,4S,5R)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidin-2-one；(2S,4S,5R)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidin；(4S)-3,4r-dimethyl-2,5c-diphenyl-[1,3,2]oxazaphospholidine 2t-oxide；N,O-(S)-phenylphosphonoyl-(-)-ephedrine；(2S,4S,5R)-3,4-dimethyl-2,5-diphenyl-1,3,2lambda5-oxazaphospholidine 2-oxide；(2S,4S,5R)-3,4-dimethyl-2,5-diphenyl-1,3,2λ5-oxazaphospholidine 2-oxide
• CAS: 54655-12-8
• 化学式: C₁₆H₁₈NO₂P
• 分子量: 287.298
• InChiKey: OCNHJHIJFNWZGN-RISOHXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-3,4-Dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine 2-oxide 、 2-Methoxyphenylmagnesium bromide 以 四氢呋喃 为溶剂， 生成 (S)-(-)-N-methyl-N-(methyl-1-hydroxy-2-phenyl-2)-ethyl-(1S,2S)-P-(2-methoxyphenyl)-P-phenyl phosphinamide
  参考文献：
  名称：

  Carey, Joseph V.; Barker Michael D.; Brown, John M., Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 831 - 840

  摘要：

  DOI：
• 作为产物：
  描述：

  盐酸麻黄碱 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2S,4S,5R)-3,4-Dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine 2-oxide
  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

• Cooper,D.B. et al., Journal of the Chemical Society. Perkin transactions I, 1977, p. 1969 - 1980
  作者：Cooper,D.B. et al.

  DOI：——

  日期：——
• Burns, Barry; Merifield, Eric; Mahon, Mary F., Journal of the Chemical Society. Perkin transactions I, 1993, # 19, p. 2243 - 2246
  作者：Burns, Barry、Merifield, Eric、Mahon, Mary F.、Molloy, Kieran C.、Wills, Martin

  DOI：——

  日期：——
• Schwalbe, Carl H.; Chopra, Geetanjlee; Freeman, Sally, Journal of the Chemical Society. Perkin transactions II, 1991, # 12, p. 2081 - 2090
  作者：Schwalbe, Carl H.、Chopra, Geetanjlee、Freeman, Sally、Brown, John M.、Carey, Joseph V.

  DOI：——

  日期：——
• 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.
• Carey, Joseph V.; Barker Michael D.; Brown, John M., Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 831 - 840
  作者：Carey, Joseph V.、Barker Michael D.、Brown, John M.、Russell, Michael J. H.

  DOI：——

  日期：——