(+/-)-bis[hydroxy(phenyl)methyl]phosphinic acid

• 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[hydroxy(phenyl)methyl]phosphinic acid
• 英文别名: bis(1-hydroxyphenylmethyl)phosphinic acid；rac-bis[hydroxy(phenyl)methyl]phosphinic acid；bis[(S)-hydroxy(phenyl)methyl]phosphinic acid
• 化学式: C₁₄H₁₅O₄P
• 分子量: 278.244
• InChiKey: YMIKTLVFXBBWKP-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-bis[hydroxy(phenyl)methyl]phosphinic acid 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 以83%的产率得到3-hydroxy-2,4-di(2-methylphenyl)-1,3-oxaphosphetane 3-oxide
  参考文献：
  名称：

  双羟烷基次膦酸分子内光信反应合成新型四元环氧膦烷的研究

  摘要：

  报道了从双羟基次膦酸合成新型四元环氧膦烷的研究。研究表明，转化是通过双羟基次膦酸与三苯基膦和偶氮二甲酸二异丙酯 (DIAD) 的混合物在甲苯-CH 2 Cl 2 中在室温下发生分子内环化反应进行的。用三苯基膦和 DIAD 的混合物处理双羟甲基次膦酸的两种非对映异构体（dl 对和内消旋），仅得到一种环状氧膦烷的立体异构体。

  DOI：

  10.1055/s-0035-1560426
• 作为产物：
  描述：

  (R)-1-phenylethanaminium (S)-hydroxy(phenyl)methyl[(S)-hydroxy(phenyl)methyl]phosphinate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以100%的产率得到(+/-)-bis[hydroxy(phenyl)methyl]phosphinic acid
  参考文献：
  名称：

  First resolution of (R,R)- and (S,S)-bis(1-hydroxyphenylmethyl)phosphinic acids via diastereomeric salt formation with enantiopure 1-phenylethylamines

  摘要：

  The resolution of racemic bis(1-hydroxyphenylmethyl)phosphinic acid with enantiopure 1-phenylethylamines via diastereomeric salt formation was investigated. X-ray crystallographic analysis of the salt clearly revealed that (S)-1-phenylethylamine was an efficient resolving agent for obtaining the single enantiomer (R,R)-bis(1-hydroxyphenylmethyl)phosphinic acid. Resolving racemic bis(1-hydroxvphenylmethyl)phosphinic acid with (R)-2-phenylethylamine gave access to (S,S)-bis(1-hydroxyphenylmethyl)phosphinic acid in good yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.004

文献信息

• A Novel Method for the Separation of Bis(α-hydroxyalkyl)phosphinic Acid Diastereoisomers via Formation of Novel Cyclic Phosphinic Acids
  作者：Babak Kaboudin、Hamideh Haghighat、Tsutomu Yokomatsu

  DOI：10.1021/jo060547h

  日期：2006.8.1

  The reaction of aromatic and aliphatic aldehydes with hypophosphorus acid under microwave irradiation was examined. The reaction gave a mixture of a racemic pair of bis(α-hydroxyalkyl)phosphinic acids and acetal derivatives from the corresponding bis(α-hydroxyalkyl)phosphinic acids of meso-stereochemistry in good yield. The difference in solubility in organic solvents due to polarity allowed us to

  在微波辐射下，研究了芳香族和脂肪族醛与次磷酸的反应。该反应得到的外消旋对双（α羟烷基）次膦酸和乙缩醛衍生物从相应的双（α羟基烷基）次膦酸的组成的混合物内消旋以良好的收率-立体化学。由于极性不同，在有机溶剂中的溶解度有所不同，因此我们可以轻松地分离这些化合物。该方法构成了一种容易，快速且产率高的制备方法，并且使用微波辐射从简单的起始原料中分离了双（α-羟烷基）次膦酸非对映异构体。
• Synthesis of a New Class of Phosphinic Acids: Synthesis of Novel Four-Membered Cyclic Oxaphosphetanes by Intramolecular Mitsunobu Reaction of Bis(α-hydroxyalkyl)phosphinic Acids
  作者：Babak Kaboudin、Hamideh Haghighat、Tsutomu Yokomatsu

  DOI：10.1055/s-0030-1260170

  日期：2011.10

  novel class of phosphinic acid derivatives, four-membered cyclic oxaphosphetanes, was synthesized by the reaction of bis(hydroxymethyl)phosphinic acids with a mixture of triphenylphosphine and diisopropyl azodicarboxylate in toluene-dichloromethane at room temperature via an intramolecular Mitsunobu reaction. bis(α-hydroxyalkyl)phosphinic acids - oxaphosphetane - cyclic phosphinic acids - Mitsunobu reaction

  通过双（羟甲基）次膦酸与三苯基膦和偶氮二羧酸二异丙酯的混合物在室温下通过分子内的Mitsunobu反应，合成了一类新型的次膦酸衍生物四元环氧杂膦酸酯。 双（α-羟烷基）次膦酸-氧杂膦烷-环状次膦酸-Mitsunobu反应
• First resolution of (R,R)- and (S,S)-bis(1-hydroxyphenylmethyl)phosphinic acids via diastereomeric salt formation with enantiopure 1-phenylethylamines
  作者：Babak Kaboudin、Hamideh Haghighat、Tsutomu Yokomatsu

  DOI：10.1016/j.tetasy.2008.03.004

  日期：2008.4

  The resolution of racemic bis(1-hydroxyphenylmethyl)phosphinic acid with enantiopure 1-phenylethylamines via diastereomeric salt formation was investigated. X-ray crystallographic analysis of the salt clearly revealed that (S)-1-phenylethylamine was an efficient resolving agent for obtaining the single enantiomer (R,R)-bis(1-hydroxyphenylmethyl)phosphinic acid. Resolving racemic bis(1-hydroxvphenylmethyl)phosphinic acid with (R)-2-phenylethylamine gave access to (S,S)-bis(1-hydroxyphenylmethyl)phosphinic acid in good yield. (C) 2008 Elsevier Ltd. All rights reserved.
• Studies on the Synthesis of Novel Four-Membered Cyclic Oxaphosphetanes via Intramolecular Mitsunobu Reaction of Bishydroxyalkylphosphinic Acids
  作者：Babak Kaboudin、Hamideh Haghighat、Tsutomu Yokomatsu

  DOI：10.1055/s-0035-1560426

  日期：——

  Studies on the synthesis of novel four-membered cyclic oxaphosphetanes from bishydroxyphosphinic acids is reported. Investigations showed that the conversion proceeds through an intramolecular Mitsunobu cyclisation of bishydroxyphosphinic acids with a mixture of triphenylphosphine and diisopropylazodicarboxylate (DIAD) in toluene–CH 2 Cl 2 at room temperature. The treatment of two diastereomers of

  报道了从双羟基次膦酸合成新型四元环氧膦烷的研究。研究表明，转化是通过双羟基次膦酸与三苯基膦和偶氮二甲酸二异丙酯 (DIAD) 的混合物在甲苯-CH 2 Cl 2 中在室温下发生分子内环化反应进行的。用三苯基膦和 DIAD 的混合物处理双羟甲基次膦酸的两种非对映异构体（dl 对和内消旋），仅得到一种环状氧膦烷的立体异构体。