5-(Diethylphosphono)-2,2-dimethyl-1-hydroxypyrrolidine | 167772-85-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 5-(Diethylphosphono)-2,2-dimethyl-1-hydroxypyrrolidine
• 英文别名: Phosphonic acid, (1-hydroxy-5,5-dimethyl-2-pyrrolidinyl)-, diethyl ester；5-diethoxyphosphoryl-1-hydroxy-2,2-dimethylpyrrolidine
• CAS: 167772-85-2
• 化学式: C₁₀H₂₂NO₄P
• 分子量: 251.263
• InChiKey: PGDYTHFEWHDOAP-UHFFFAOYSA-N

物化性质

• 沸点：
  348.4±22.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(Diethylphosphono)-2,2-dimethyl-1-hydroxypyrrolidine 在 ammonium hydroxide 、 copper diacetate 、 air 作用下， 以 乙醇 、 苯 为溶剂， 反应 0.17h， 生成 2-diethoxyphosphoryl-2,5,5-trimethylpyrrolidine-N-oxyl radical
  参考文献：
  名称：

  Identification of Reactive Free Radicals with a New 31P-Labeled DMPO Spin Trap

  摘要：

  The P-31 atom (I = 1/2) can provide additional useful EPR information when it is introduced into the 5,5-dimethyl-1-pyrroline N-oxide (DMPO) spin trap. 2-(Diethylphosphono)-5,5-dimethyl-1-pyrroline N-oxide (DEP-DMPO) has been synthesized by addition of diethylphosphono anion to DMPO followed by oxidation with copper acetate/air in 95% ethanol. DEP-DMPO is a liquid at room temperature and soluble in both aqueous and organic solutions. A variety of spin trapping experiments have been explored. The main feature of the EPR spectra of DEP-DMPO spin adducts is the relatively large doublet of triplets. The P-31 hyperfine splitting constant (P-31-hfsc or a(p)) in these examples is always larger than the N-hfsc. For oxygen-centered radical adducts, e.g., from HOO., HO., n-BuO(.), i-BuO(.), and isoamylO(.), a(P)'s are 32.3-34.5 G whereas a(N)'s are 13.4-14.1 G in water. For acyl adducts, such as CH3(CH2)(4)C(O)(.), C2H5C(O)(.), CH3C(O)(.), and (CO2)-C-., a(P)'s are 38.6-39.2 G whereas a(N)'s are 14.3-14.8 G in water; a(P)'s for alkyl and hydroxyalkyl radical adducts are between 48.1 and 54.6 G in water; for the phenyl adduct the value is exceptionally small, a(p) = 31.5 G. Most of the adducts are very persistent in aqueous solutions, e.g., t(1/2) = 3.0 h for HO. adduct, 31.5 h for i-amylO(.) adduct, and 52.4 h for CH3C(O)(.) adduct in water. However, the hydroperoxyl and tert-butylperoxyl adducts decay rapidly: t(1/2) = 3.6 s in water and t(1/2) = 4.3 s in isooctane, respectively.

  DOI：

  10.1021/jo00122a022
• 作为产物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 、 亚磷酸二乙酯 在 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 生成 5-(Diethylphosphono)-2,2-dimethyl-1-hydroxypyrrolidine
  参考文献：
  名称：

  Identification of Reactive Free Radicals with a New 31P-Labeled DMPO Spin Trap

  摘要：

  The P-31 atom (I = 1/2) can provide additional useful EPR information when it is introduced into the 5,5-dimethyl-1-pyrroline N-oxide (DMPO) spin trap. 2-(Diethylphosphono)-5,5-dimethyl-1-pyrroline N-oxide (DEP-DMPO) has been synthesized by addition of diethylphosphono anion to DMPO followed by oxidation with copper acetate/air in 95% ethanol. DEP-DMPO is a liquid at room temperature and soluble in both aqueous and organic solutions. A variety of spin trapping experiments have been explored. The main feature of the EPR spectra of DEP-DMPO spin adducts is the relatively large doublet of triplets. The P-31 hyperfine splitting constant (P-31-hfsc or a(p)) in these examples is always larger than the N-hfsc. For oxygen-centered radical adducts, e.g., from HOO., HO., n-BuO(.), i-BuO(.), and isoamylO(.), a(P)'s are 32.3-34.5 G whereas a(N)'s are 13.4-14.1 G in water. For acyl adducts, such as CH3(CH2)(4)C(O)(.), C2H5C(O)(.), CH3C(O)(.), and (CO2)-C-., a(P)'s are 38.6-39.2 G whereas a(N)'s are 14.3-14.8 G in water; a(P)'s for alkyl and hydroxyalkyl radical adducts are between 48.1 and 54.6 G in water; for the phenyl adduct the value is exceptionally small, a(p) = 31.5 G. Most of the adducts are very persistent in aqueous solutions, e.g., t(1/2) = 3.0 h for HO. adduct, 31.5 h for i-amylO(.) adduct, and 52.4 h for CH3C(O)(.) adduct in water. However, the hydroperoxyl and tert-butylperoxyl adducts decay rapidly: t(1/2) = 3.6 s in water and t(1/2) = 4.3 s in isooctane, respectively.

  DOI：

  10.1021/jo00122a022

文献信息

• Identification of Reactive Free Radicals with a New 31P-Labeled DMPO Spin Trap
  作者：Edward G. Janzen、Yong-Kang Zhang

  DOI：10.1021/jo00122a022

  日期：1995.9

  The P-31 atom (I = 1/2) can provide additional useful EPR information when it is introduced into the 5,5-dimethyl-1-pyrroline N-oxide (DMPO) spin trap. 2-(Diethylphosphono)-5,5-dimethyl-1-pyrroline N-oxide (DEP-DMPO) has been synthesized by addition of diethylphosphono anion to DMPO followed by oxidation with copper acetate/air in 95% ethanol. DEP-DMPO is a liquid at room temperature and soluble in both aqueous and organic solutions. A variety of spin trapping experiments have been explored. The main feature of the EPR spectra of DEP-DMPO spin adducts is the relatively large doublet of triplets. The P-31 hyperfine splitting constant (P-31-hfsc or a(p)) in these examples is always larger than the N-hfsc. For oxygen-centered radical adducts, e.g., from HOO., HO., n-BuO(.), i-BuO(.), and isoamylO(.), a(P)'s are 32.3-34.5 G whereas a(N)'s are 13.4-14.1 G in water. For acyl adducts, such as CH3(CH2)(4)C(O)(.), C2H5C(O)(.), CH3C(O)(.), and (CO2)-C-., a(P)'s are 38.6-39.2 G whereas a(N)'s are 14.3-14.8 G in water; a(P)'s for alkyl and hydroxyalkyl radical adducts are between 48.1 and 54.6 G in water; for the phenyl adduct the value is exceptionally small, a(p) = 31.5 G. Most of the adducts are very persistent in aqueous solutions, e.g., t(1/2) = 3.0 h for HO. adduct, 31.5 h for i-amylO(.) adduct, and 52.4 h for CH3C(O)(.) adduct in water. However, the hydroperoxyl and tert-butylperoxyl adducts decay rapidly: t(1/2) = 3.6 s in water and t(1/2) = 4.3 s in isooctane, respectively.