(S_P,S)-N-(1-phenylethyl)amino-tert-butylphenylphosphine oxide | 538311-41-0

• 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: (S_P,S)-N-(1-phenylethyl)amino-tert-butylphenylphosphine oxide
• 英文别名: (SP,S)-tert-butyl(α-methylbenzylamino)phenylphosphine oxide；P-(tert-butyl)-P-phenyl-N-((S)-1-phenylethyl)phosphinic amide；(1S)-N-[tert-butyl(phenyl)phosphoryl]-1-phenylethanamine
• CAS: 538311-41-0
• 化学式: C₁₈H₂₄NOP
• mdl: MFCD09863833
• 分子量: 301.368
• InChiKey: RLBMIUWPBJMKRP-YCRPNKLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S_P,S)-N-(1-phenylethyl)amino-tert-butylphenylphosphine oxide 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (S)-P-(tert-butyl)-P-phenylphosphinic amide
  参考文献：
  名称：

  通过转移氢化使次膦（硫）酰胺与醇进行N-烷基化的实用方法。

  摘要：

  该手稿描述了通过转移氢化从伯或仲醇和伯次膦酰胺（R 1 R 2 P = ONH 2）亲核试剂制备N-烷基次膦酰胺的模块化方法。该转化通常以优异的收率进行，使用方便获得的试剂，并且产生水作为唯一的副产物。

  DOI：

  10.1016/j.tet.2019.04.029
• 作为产物：
  描述：

  N-(1-methylbenzyl)amino-tert-butylphenylphosphine 在 硼烷 、 双氧水 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 (S_P,S)-N-(1-phenylethyl)amino-tert-butylphenylphosphine oxide
  参考文献：
  名称：

  手性胺与外消旋氯膦的立体选择性反应

  摘要：

  外消旋氯膦与手性 l-苯乙胺或氨基酸酯发生立体选择性反应，得到富含非对映异构体的氨基膦 3，将其分离为非对映异构纯结晶硼烷配合物。氧化、硫化、与甲基碘的反应提供氨基膦的旋光衍生物。次膦酸酰胺的 (R,S)-和 (S,S)-立体异构体通过结晶和快速色谱法分离。研究了磷酸酰胺的立体化学性质。三价磷原子的不对称诱导机制被合理化。

  DOI：

  10.1080/10426500490459650

文献信息

• Stereoselective addition of Grignard reagents to new P-chirogenic N-phosphinoylimines
  作者：Irene Notar Francesco、Alain Wagner、Françoise Colobert

  DOI：10.1039/b915781f

  日期：——

  The addition of various Grignard reagents to P-t-butyl-P-phenyl-N-phosphinoyl benzaldimine provides a stereoselective method for the synthesis of chiral phosphinoylamines.

  向Pt-丁基-P-苯基-N-膦酰基苯甲二胺中添加各种格氏试剂为合成手性膦酰基胺提供了立体选择方法。
• Stereoselective Addition of Grignard Reagents to New P-Chirogenic N-Phosphinoylbenzaldimines: Effect of the Phosphorus Substituents on the Stereoselectivity
  作者：Irene Notar Francesco、Coraline Egloff、Alain Wagner、Françoise Colobert

  DOI：10.1002/ejoc.201100380

  日期：2011.7

  give both diastereoisomers in high yields and with promising diastereomeric ratios. Then N-[(tert-butyl)(phenyl)phosphinoyl]benzaldimine, which displayed the best results, was subjected to the 1,2-addition of various Grignard reagents to evaluate the best chiral induction due to the stereogenic phosphorus atom. The corresponding adducts were obtained in excellent yields and with moderate to excellent diastereoisomeric

  通过从合适的氧化膦开始，通过五个步骤合成了几种膦亚胺，然后用甲基溴化镁处理，以高产率和有希望的非对映异构体比例得到两种非对映异构体。然后将显示出最佳结果的 N-[(叔丁基)(苯基)膦酰基]苯扎二亚胺进行各种格氏试剂的 1,2-加成，以评估由于立体磷原子引起的最佳手性诱导。以极好的收率和中等至极好的非对映异构体比率获得了相应的加合物。
• Stereoselective Reactions of Optically Active Derivatives of α-Methylbenzylaminophosphine
  作者：O. I. Kolodyazhnyi、N. V. Andrushko、E. V. Grishkun

  DOI：10.1023/b:rugc.0000031849.78207.1c

  日期：2004.4

  A number of N+(alpha-methylbenzyl) phosphorus amides were synthesized, and their stereochemical properties were studied. Reactions of achiral chlorophosphines with optically active alpha-methylbenzylamine are accompanied by asymmetric induction at the phosphorus atom to give optically active diastereoisomers of N-(alpha-methylbenzyl)aminophosphines, which were isolated as the corresponding borane complexes with 100% optical purity. Stereochemically pure (R,S)-aminophosphines were obtained by decomposition of these complexes via treatment with diethylamine. Their oxidation, sulfurization, and alkylation with methyl iodide afforded optically active aminophosphine derivatives. Hydrolysis of (R,S)-aminophosphines gave optically active tert-butylphenylphosphine oxide and phosphonic acid amides. (R,S)- and (S,S)-Diastereoisomers of N-(alpha-methylbenzyl)phosphinic amides were separated by crystallization and flash chromatography, and their absolute configuration was established. Also, derivatives of bis- and tris(alpha-methylbenzylamino)phosphines were synthesized.
• Asymmetric synthesis of chiral N-(1-methylbenzyl)aminophosphines
  作者：Oleg I. Kolodiazhnyi、Evgenyi V. Gryshkun、Natalia V. Andrushko、Matthias Freytag、Peter G. Jones、Reinhard Schmutzler

  DOI：10.1016/s0957-4166(02)00750-4

  日期：2003.1

  The reactions of chlorophosphines 1 with (S)- or (R)-1-methylbenzylamines 2 proceed stereoselectively to give N-(1-methylbenzyl)aminophosphines 3, which were isolated as crystalline borane complexes with 100% diastereomeric purity. The absolute configuration of the new chiral compounds was established by X-ray analysis and chemical extrapolation. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A practical method for N-alkylation of phosphinic (thio)amides with alcohols via transfer hydrogenation
  作者：Tanner C. Jankins、Zi-Yang Qin、Keary M. Engle

  DOI：10.1016/j.tet.2019.04.029

  日期：2019.6

  This manuscript describes a modular method for preparing N-alkyl phosphinic amides from primary or secondary alcohols and primary phosphinic amide (R1R2P = ONH2) nucleophiles via transfer hydrogenation. The transformation typically proceeds in excellent yields, employs conveniently available reagents, and produces water as the only byproduct.

  该手稿描述了通过转移氢化从伯或仲醇和伯次膦酰胺（R 1 R 2 P = ONH 2）亲核试剂制备N-烷基次膦酰胺的模块化方法。该转化通常以优异的收率进行，使用方便获得的试剂，并且产生水作为唯一的副产物。