isopropyl(1-hydroxymethyl)phenylphosphine oxide | 106649-32-5

• 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: isopropyl(1-hydroxymethyl)phenylphosphine oxide
• 英文别名: (hydroxymethyl)phenylisopropylphosphine oxide；[Phenyl(propan-2-yl)phosphoryl]methanol
• CAS: 106649-32-5
• 化学式: C₁₀H₁₅O₂P
• 分子量: 198.202
• InChiKey: SBDUHOSWUSXKIA-UHFFFAOYSA-N

物化性质

• 熔点：
  104.5-106 °C
• 沸点：
  370.5±34.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 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：

  isopropyl(1-hydroxymethyl)phenylphosphine oxide 在 五氯化磷 作用下， 以 苯 为溶剂， 反应 0.5h， 以88%的产率得到[chloromethyl(propan-2-yl)phosphoryl]benzene
  参考文献：
  名称：

  Patsanovskii, I. I.; Ishmaeva, E. A.; Sundukova, E. N., Journal of general chemistry of the USSR, 1986, vol. 56, # 3, p. 501 - 509

  摘要：

  DOI：
• 作为产物：
  描述：

  聚合甲醛 、 isopropyl(phenyl)phosphine oxide 在 sodium 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以80%的产率得到isopropyl(1-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

• Enhancement of Enantioselectivity in the Optical Resolution of Primary Alcohols with Modified Cyclodextrin Colyophilized Lipase
  作者：Kosei Shioji、Yoshimitsu Kurauchi、Keiko Terada、Yasushi Kodera、Kentaro Okuma

  DOI：10.1080/00397910701386154

  日期：2007.7.1
• PATSANOVSKIJ, I. I.;ISHMAEVA, EH. A.;SUNDUKOVA, E. N.;YARKEVICH, A. N.;TS+, ZH. OBSHCH. XIMII, 1986, 56, N 3, 567-576
  作者：PATSANOVSKIJ, I. I.、ISHMAEVA, EH. A.、SUNDUKOVA, E. N.、YARKEVICH, A. N.、TS+

  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.
• Patsanovskii, I. I.; Ishmaeva, E. A.; Sundukova, E. N., Journal of general chemistry of the USSR, 1986, vol. 56, # 3, p. 501 - 509
  作者：Patsanovskii, I. I.、Ishmaeva, E. A.、Sundukova, E. N.、Yarkevich, A. N.、Tsvetkov, E. N.

  DOI：——

  日期：——