(2S,4S,5R)-3,4-dimethyl-2-hydrazino-5-phenyl-1,3,2-oxazaphospholidin-2-one | 123709-67-1

• 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-hydrazino-5-phenyl-1,3,2-oxazaphospholidin-2-one
• 英文别名: (2S,4S,5R)-3,4-dimethyl-2-hydrazido-5-phenyl-1,3,2-oxazaphospholidin-2-oxide；[(2R,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ5-oxazaphospholidin-2-yl]hydrazine
• CAS: 123709-67-1
• 化学式: C₁₀H₁₆N₃O₂P
• 分子量: 241.23
• InChiKey: YQIDXKACIZDOHQ-ACZUWMGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.59
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-3,4-dimethyl-2-hydrazino-5-phenyl-1,3,2-oxazaphospholidin-2-one 、 3-环己烯甲醛 以 乙醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Dehmlow, Eckehard V.; Sauerbier, Christiane, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1989, vol. 44, # 2, p. 240 - 242

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one 在 盐酸肼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(2S,4S,5R)-3,4-dimethyl-2-hydrazino-5-phenyl-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

• DEHMLOW, ECKEHARD V.;SAUERBIER, CHRISTIANE, Z. NATURFORSCH. B, 44,(1989) N, C. 240-242
  作者：DEHMLOW, ECKEHARD V.、SAUERBIER, CHRISTIANE

  DOI：——

  日期：——