(1-hydroxy-1-methylethyl)(methyl)phenylphosphine oxide

• 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: (1-hydroxy-1-methylethyl)(methyl)phenylphosphine oxide
• 英文别名: methyl(α-hydroxyisopropyl)phenylphosphine oxide；2-[Methyl(phenyl)phosphoryl]propan-2-ol
• 化学式: C₁₀H₁₅O₂P
• 分子量: 198.202
• InChiKey: XGTRANNSDNGFRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dimethyl sulfide borane 、 (1-hydroxy-1-methylethyl)(methyl)phenylphosphine oxide 以 四氢呋喃 为溶剂， 反应 2.03h， 以87%的产率得到(1-hydroxy-1-methylethyl)(methyl)phenylphosphine borane
  参考文献：
  名称：

  Reduction of Functionalized Tertiary Phosphine Oxides with BH₃

  摘要：

  A direct stereoselective conversion of tertiary hydroxyalkylphosphine oxides to the corresponding tertiary hydroxyalkylphosphineboranes involving facile reduction of the P=O bond by BH3 under mild conditions has been developed. The unprecedented facility of reduction of the strong P=O bond by BH3, a mild reducing agent, has been achieved through an intramolecular P=O center dot center dot center dot B complexation directed by proximal alpha- or beta-hydroxy groups present in the phosphine oxide structures. As established by two chemical correlations, the developed transformation of hydroxyalkylphosphine oxides into hydroxyalkylphosphine-boranes takes place with complete inversion of configuration at P.

  DOI：

  10.1021/jo502623g
• 作为产物：
  描述：

  methyl(phenyl)phosphineoxide 、 丙酮 反应 72.0h， 以30%的产率得到(1-hydroxy-1-methylethyl)(methyl)phenylphosphine oxide
  参考文献：
  名称：

  Reduction of Functionalized Tertiary Phosphine Oxides with BH₃

  摘要：

  A direct stereoselective conversion of tertiary hydroxyalkylphosphine oxides to the corresponding tertiary hydroxyalkylphosphineboranes involving facile reduction of the P=O bond by BH3 under mild conditions has been developed. The unprecedented facility of reduction of the strong P=O bond by BH3, a mild reducing agent, has been achieved through an intramolecular P=O center dot center dot center dot B complexation directed by proximal alpha- or beta-hydroxy groups present in the phosphine oxide structures. As established by two chemical correlations, the developed transformation of hydroxyalkylphosphine oxides into hydroxyalkylphosphine-boranes takes place with complete inversion of configuration at P.

  DOI：

  10.1021/jo502623g

文献信息

• Reaction of boryloxyalkylphosphines with amines
  作者：B. A. Arbuzov、G. N. Nikonov、O. A. Erastov

  DOI：10.1007/bf00953232

  日期：1986.3
• ARBUZOV, B. A.;NIKONOV, G. N.;ERASTOV, O. A., IZV. AN CCCP. CEP. XIM., 1986, N 3, 643-648
  作者：ARBUZOV, B. A.、NIKONOV, G. N.、ERASTOV, O. A.

  DOI：——

  日期：——
• Reduction of Functionalized Tertiary Phosphine Oxides with BH₃
  作者：Sylwia Sowa、Marek Stankevič、Anna Szmigielska、Hanna Małuszyńska、Anna E. Kozioł、K. Michał Pietrusiewicz

  DOI：10.1021/jo502623g

  日期：2015.2.6

  A direct stereoselective conversion of tertiary hydroxyalkylphosphine oxides to the corresponding tertiary hydroxyalkylphosphineboranes involving facile reduction of the P=O bond by BH3 under mild conditions has been developed. The unprecedented facility of reduction of the strong P=O bond by BH3, a mild reducing agent, has been achieved through an intramolecular P=O center dot center dot center dot B complexation directed by proximal alpha- or beta-hydroxy groups present in the phosphine oxide structures. As established by two chemical correlations, the developed transformation of hydroxyalkylphosphine oxides into hydroxyalkylphosphine-boranes takes place with complete inversion of configuration at P.