(+/-)-(2S,3R,5R,6S)-3,5,6-triphenyl-2-hydrogeno-2-oxo-1,4,2-oxazaphosphinane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+/-)-(2S,3R,5R,6S)-3,5,6-triphenyl-2-hydrogeno-2-oxo-1,4,2-oxazaphosphinane
• 英文别名: (3R,5R,6S)-2-oxido-3,5,6-triphenyl-1,4,2-oxazaphosphinan-2-ium
• 化学式: C₂₁H₂₀NO₂P
• 分子量: 349.369
• InChiKey: QVWNIYUBBWIJQG-QHAWAJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(2S,3R,5R,6S)-3,5,6-triphenyl-2-hydrogeno-2-oxo-1,4,2-oxazaphosphinane 在 palladium on activated charcoal 盐酸 、 四(三苯基膦)钯 、 氢气 、 三乙胺 作用下， 以 水 、 甲苯 为溶剂， 20.0~110.0 ℃ 、101.33 kPa 条件下， 反应 25.0h， 生成 benzyl(phenyl)phosphinic acid
  参考文献：
  名称：

  Pallado-catalysed P-arylations and P-vinylation of 2-hydrogeno-2-oxo-1,4,2-oxazaphosphinanes

  摘要：

  A simple and effective preparation of 2-aryl-(or 2-vinyl)-1,4,2-oxazaphosphines. phosphorus analogues of aryl-morpholinols has been developed. involving palladium catalysed coupling of aryl (or vinyl)-halides with 2-H-1,4,2-oxazaphosphinane in presence of triethylamine. A deprotection step was also proposed to afford the corresponding P-aryl-alpha-aminobenzylphosphinic acid. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.007
• 作为产物：
  描述：

  (+/-)-erythro-α'-benzylidenamino-bibenzyl-α-ol; N-benzylidene-dl-diphenylhydroxyethylamine 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 42.0h， 生成 (+/-)-(2S,3R,5R,6S)-3,5,6-triphenyl-2-hydrogeno-2-oxo-1,4,2-oxazaphosphinane
  参考文献：
  名称：

  具有5或6元环的新型磷杂环的合成，反应性和立体化学

  摘要：

  开发了包含α-氨基或α-羟基膦酸或次膦酸基序的新型磷杂环的合成。2,3-二氢-1,3-氧杂磷腈（1）和1,4,2-氧杂氮杂膦（2）具有反应性，分别是烯醇醚部分和PH键，可进行各种结构修饰：对于1a，通过引入氨基取代基，（ii）对于2a，通过羟基或氨基烷基化，通过迈克尔加成或通过P-芳基化。这些反应通常表现出良好的或什至优异的动力学非对映选择性，这通常可以通过过渡态的分子模型来预测。

  DOI：

  10.1016/j.jorganchem.2004.11.035

文献信息

• Diastereoselective Addition of 2<i>H</i>-2-Oxo-1,4,2-oxazaphosphinanes to Aldehydes and Imines
  作者：Jean-Luc Pirat、Jérôme Monbrun、David Virieux、Jean-Noël Volle、Monique Tillard、Henri-Jean Cristau

  DOI：10.1021/jo050201r

  日期：2005.9.1

  Diastereoselective additions of 2-hydrogeno-2-oxo-1,4,2-oxazaphosphinanes to aldehydes and imines are described. α,α‘-Diaminophosphinic and α-amino-α‘-hydroxyphosphinic derivatives were obtained with de's ranging from 24 to 90%.

  描述了将2-氢-2-氧代-1,4,2-氧杂氮杂膦酸酯非对映选择性加成到醛和亚胺上。得到的α，α′-二氨基次膦酸和α-氨基-α′-羟基次膦酸衍生物的de′范围为24-90％。
• Diastereoselective Michael addition of 2H-2-oxo-1,4,2-oxaza phosphinanes to olefins
  作者：Jérôme Monbrun、Bénédicte Dayde、Henri-Jean Cristau、Jean-Noël Volle、David Virieux、Jean-Luc Pirat

  DOI：10.1016/j.tet.2010.10.078

  日期：2011.1

  Diastereoselective Michael additions of 2-hydrogeno-2-oxo-1,4,2-oxazaphosphinanes to olefins were described. Phosphinopeptide compounds were obtained in very good yield (up to 90%) and diasteromeric excesses ranging from 26 to 78%. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• First syntheses of 2-hydrogeno-2-oxo-1,4,2-oxazaphosphinanes via intramolecular esterification
  作者：Henri-Jean Cristau、Jérôme Monbrun、Monique Tillard、Jean-Luc Pirat

  DOI：10.1016/s0040-4039(03)00446-5

  日期：2003.4

  Synthesis of 2-hydrogeno-2-oxo-1,4,2-oxazaphosphinanes via either intramolecular transesterification, using potassium tort-butylate as catalytic agent, or phosphinic acid esterification, is described for the first time. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Pallado-catalysed P-arylations and P-vinylation of 2-hydrogeno-2-oxo-1,4,2-oxazaphosphinanes
  作者：Jean-Luc Pirat、Jérôme Monbrun、David Virieux、Henri-Jean Cristau

  DOI：10.1016/j.tet.2005.05.007

  日期：2005.7

  A simple and effective preparation of 2-aryl-(or 2-vinyl)-1,4,2-oxazaphosphines. phosphorus analogues of aryl-morpholinols has been developed. involving palladium catalysed coupling of aryl (or vinyl)-halides with 2-H-1,4,2-oxazaphosphinane in presence of triethylamine. A deprotection step was also proposed to afford the corresponding P-aryl-alpha-aminobenzylphosphinic acid. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis, reactivity and stereochemistry of new phosphorus heterocycles with 5- or 6-membered rings
  作者：Henri-Jean Cristau、Jean-Luc Pirat、David Virieux、Jérôme Monbrun、Ciptadi Ciptadi、Yves-Alain Bekro

  DOI：10.1016/j.jorganchem.2004.11.035

  日期：2005.5

  Syntheses of novel phosphorus heterocycles containing α-amino or α-hydroxyphosphonic or phosphinic acids motifs are developed. 2,3-dihydro-1,3-oxaphospholes (1) and 1,4,2-oxazaphosphinanes (2) exhibit a reactive part, respectively the enolether moiety and the P–H bond, which allows various structural modifications: (i) for 1a, by introduction of amino substituents, (ii) for 2a, by hydroxy- or aminoalkylation

  开发了包含α-氨基或α-羟基膦酸或次膦酸基序的新型磷杂环的合成。2,3-二氢-1,3-氧杂磷腈（1）和1,4,2-氧杂氮杂膦（2）具有反应性，分别是烯醇醚部分和PH键，可进行各种结构修饰：对于1a，通过引入氨基取代基，（ii）对于2a，通过羟基或氨基烷基化，通过迈克尔加成或通过P-芳基化。这些反应通常表现出良好的或什至优异的动力学非对映选择性，这通常可以通过过渡态的分子模型来预测。