cyclohexyl(hydroxymethyl)phenylphosphine oxide | 377775-20-7

• 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: cyclohexyl(hydroxymethyl)phenylphosphine oxide
• 英文别名: [Cyclohexyl(phenyl)phosphoryl]methanol
• CAS: 377775-20-7
• 化学式: C₁₃H₁₉O₂P
• 分子量: 238.266
• InChiKey: GOUZHMRHHKTFAU-UHFFFAOYSA-N

物化性质

• 沸点：
  434.7±37.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  硼烷四氢呋喃络合物 、 cyclohexyl(hydroxymethyl)phenylphosphine oxide 以 四氢呋喃 为溶剂， 反应 4.03h， 以90%的产率得到cyclohexyl(1-hydroxymethyl)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：

  聚合甲醛 、 cyclohexyl(phenyl)phosphine oxide 在 sodium 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以94%的产率得到cyclohexyl(hydroxymethyl)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

• Lipase-catalyzed kinetic resolution of P-chiral phosphorus compounds: enantiopreference of Pseudomonas lipase and Candida antarctica lipase
  作者：Kosei Shioji、Yuichiro Ueno、Yoshimitsu Kurauchi、Kentaro Okuma

  DOI：10.1016/s0040-4039(01)01349-1

  日期：2001.9

  Optically active 1-hydroxymethylalkylphenylphosphine oxides la-c were prepared by Pseudomonas fluorescens lipase (lipase AK) and Candida antarctica lipase (CAL)-catalyzed optical resolution. Lipase AK-catalyzed resolution of tert-butyl derivative 1c showed R-selectivity, whereas CAL preferred the S-enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.