1-(N,N-diisopropylamino)-2,2-dimethyl-1-oxophospholane | 143237-89-2

• 英文名称: 1-(N,N-diisopropylamino)-2,2-dimethyl-1-oxophospholane
• 英文别名: 2,2-dimethyl-1-oxo-N,N-di(propan-2-yl)-1λ5-phospholan-1-amine
• CAS: 143237-89-2
• 化学式: C₁₂H₂₆NOP
• 分子量: 231.318
• InChiKey: SSWVORINLVMXDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R*,2R*)-1-(N,N-diisopropylamino)-1-oxo-2-methyl-phospholane 、 碘甲烷 在 lithium diisopropyl amide 作用下， 生成 1-(N,N-diisopropylamino)-2,2-dimethyl-1-oxophospholane 、 (2R*,5R*)-1-(N,N-diisopropylamino)-2,5-dimethyl-1-oxophospholane
  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.