bis(hydroxymethyl)phenylphosphine-borane | 869707-38-0

• 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: bis(hydroxymethyl)phenylphosphine-borane
• 英文别名: [Bis(hydroxymethyl)-phenylphosphaniumyl]boranuide；[bis(hydroxymethyl)-phenylphosphaniumyl]boranuide
• CAS: 869707-38-0
• 化学式: C₈H₁₄BO₂P
• 分子量: 183.983
• InChiKey: SAVYASBNKKGNKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(hydroxymethyl)phenylphosphine-borane 在 Candida antarctica lipase B 、 phosphate buffer 作用下， 以 四氢呋喃 、 异丙醚 为溶剂， 反应 104.0h， 生成 (R)-acetyloxymethyl(hydroxymethyl)phenylphosphine-borane
  参考文献：
  名称：

  A Biocatalytic Route to P-Chirogenic Compounds by Lipase-Catalyzed Desymmetrization of a Prochiral Phosphine−Borane

  摘要：

  [GRAPHICS]Available methods for synthesis of P-chirogenic compounds are limited. We set out to find biocatalytical means to introduce asymmetry in a phosphine-borane. After screening different lipases, Candida antarctica lipase B was found to give excellent results in the desymmetrization of prochiral phosphine-boranes. Both enantiomers can be obtained in up to > 98% optical purity via acetylation or hydrolysis in processes that allow recycling of the substrates.

  DOI：

  10.1021/ol0519893
• 作为产物：
  描述：

  聚合甲醛 、 苯基膦 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以92%的产率得到bis(hydroxymethyl)phenylphosphine-borane
  参考文献：
  名称：

  A Biocatalytic Route to P-Chirogenic Compounds by Lipase-Catalyzed Desymmetrization of a Prochiral Phosphine−Borane

  摘要：

  [GRAPHICS]Available methods for synthesis of P-chirogenic compounds are limited. We set out to find biocatalytical means to introduce asymmetry in a phosphine-borane. After screening different lipases, Candida antarctica lipase B was found to give excellent results in the desymmetrization of prochiral phosphine-boranes. Both enantiomers can be obtained in up to > 98% optical purity via acetylation or hydrolysis in processes that allow recycling of the substrates.

  DOI：

  10.1021/ol0519893

文献信息

• A Biocatalytic Route to P-Chirogenic Compounds by Lipase-Catalyzed Desymmetrization of a Prochiral Phosphine−Borane
  作者：Daniel Wiktelius、Magnus J. Johansson、Kristina Luthman、Nina Kann

  DOI：10.1021/ol0519893

  日期：2005.10.1

  [GRAPHICS]Available methods for synthesis of P-chirogenic compounds are limited. We set out to find biocatalytical means to introduce asymmetry in a phosphine-borane. After screening different lipases, Candida antarctica lipase B was found to give excellent results in the desymmetrization of prochiral phosphine-boranes. Both enantiomers can be obtained in up to > 98% optical purity via acetylation or hydrolysis in processes that allow recycling of the substrates.