o-anisyl-(2-hydroxyethyl)phenylphosphine borane | 127687-01-8

• 英文名称: o-anisyl-(2-hydroxyethyl)phenylphosphine borane
• 英文别名: (S)-o-anisyl(2-hydroxyethyl)phenylphosphine-borane
• CAS: 127687-01-8
• 化学式: C₁₅H₂₀BO₂P
• 分子量: 274.107
• InChiKey: YMVLJWMAYVPZFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  o-anisyl-(2-hydroxyethyl)phenylphosphine borane 在 tetrafluoroboric acid 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 2-[(2-methoxyphenyl)-phenylphosphanyl]ethanol
  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：

  o-anisylphenylphosphine oxide 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 48.28h， 生成 o-anisyl-(2-hydroxyethyl)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

文献信息

• Synthesis and reactions of phosphine-boranes. Synthesis of new bidentate ligands with homochiral phosphine centers via optically pure phosphine-boranes
  作者：Tsuneo Imamoto、Toshiyuki Oshiki、Takashi Onozawa、Tetsuo Kusumoto、Kazuhiko Sato

  DOI：10.1021/ja00169a036

  日期：1990.6
• Iridium Complexes with Phosphine−Phosphite Ligands. Structural Aspects and Application in the Catalytic Asymmetric Hydrogenation of N-Aryl Imines
  作者：Sergio Vargas、Miguel Rubio、Andrés Suárez、Diego del Río、Eleuterio Álvarez、Antonio Pizzano

  DOI：10.1021/om050885t

  日期：2006.2.1

  A family of modularly designed phosphine-phosphites (P-OP), possessing a C-C-O backbone, has been synthesized and evaluated in the iridium-catalyzed asymmetric hydrogenation of N-aryl imines. The enantioselectivity of this reaction is highly dependent on the nature of the ligand, and catalysts bridged by an oxyethylene fragment have produced significantly higher enantiomeric excesses (Delta ee > 20%) than their o-oxyphenylene counterparts. Structural studies by X-ray crystallography and NMR spectroscopy of complexes with the formulation [Ir(COD)(P-OP)]BF4 and Ir(Cl)(CO)(P-OP), complemented by DFT calculations of model compounds of the chlorocarbonyls, have shown important differences between complexes bridged by an aliphatic or an aromatic bridge, regarding the iridacycle conformation and the location of phosphine substiments. Catalyst optimization has afforded enantioselectivities from 72 to 85% ee in the hydrogenation of several N-aryl imines.