(2R*,5R*)-2,5-dimethylphospholanic acid | 143237-92-7

• 英文名称: (2R*,5R*)-2,5-dimethylphospholanic acid
• 英文别名: (2R,5R)-1-hydroxy-2,5-dimethyl-1lambda5-phospholane 1-oxide；(2R,5R)-1-hydroxy-2,5-dimethyl-1λ5-phospholane 1-oxide
• CAS: 143237-92-7
• 化学式: C₆H₁₃O₂P
• 分子量: 148.142
• InChiKey: DYWBYURXPZTNTK-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2R*,5R*)-1-(N,N-diisopropylamino)-2,5-dimethyl-1-oxophospholane 在 盐酸 作用下， 以68%的产率得到(2R*,5R*)-2,5-dimethylphospholanic acid
  参考文献：
  名称：

  Polniaszek, Richard P., Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 75, # 1-4, p. 127 - 130

  摘要：

  DOI：

文献信息

• Preparation of (2S*,5S*)-2,5-dibenzylphospholanic acid
  作者：Richard P. Polniaszek

  DOI：10.1021/jo00045a035

  日期：1992.9

  The cheletropic cycloaddition of [CIP(N-i-Pr2)]+AlCl4- with 1-substituted dienes at 0-degrees-C afforded 1-(N,N-diisoprophyamino)-1-chloro-2-alkyl-DELTA-3-phospholenium tetrachloroaluminates. The stereoselectivity of these reactions ranged from 5:1 to 100:0. Hydrolysis of the cycloadducts afforded a diastereomeric mixture of 1-(N,N-diisopropylamino)-1-oxo-2-alkyl-DELTA-3-phospholenes. The ratio of the DELTA-3-phospholene amides differed significantly from the ratio of the intermediate DELTA-3-phospholenium ions, implying that the hydrolysis reactions occurred via five-coordinate phosphoranes which underwent pseudorotation prior to elimination of HCI. Hydrogenation of the DELTA-3-phospholene amides afforded saturated phospholane amides which underwent regioselective deprotonation and subsequent stereospecific alkylation reactions with alkyl halides. 1-(N,N-Diisopropylamino)-1-oxo-2,5-dimethyl- and -2,5-dibenzylphospholanes (10a and 10b) were converted by acid-promoted hydrolysis to (2R*,5R*)-2,5-dimethyl- and (2S*,5S*)-2,5-dibenzylphospholanic acid (12a and 12b), respectively.