(S,S,S)-azaphosphatrane oxide

• 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,S,S)-azaphosphatrane oxide
• 英文别名: 2,8,9-tris[(1S)-1-phenylethyl]-2,5,8,9-tetraza-1lambda5-phosphabicyclo[3.3.3]undecane 1-oxide；2,8,9-tris[(1S)-1-phenylethyl]-2,5,8,9-tetraza-1λ5-phosphabicyclo[3.3.3]undecane 1-oxide
• 化学式: C₃₀H₃₉N₄OP
• 分子量: 502.64
• InChiKey: CEEZKAMGWQCMES-QKDODKLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  次氮基三乙酸 在 亚磷酸三苯酯 、 lithium aluminium tetrahydride 、 双(三甲基硅基)过氧化物 、 potassium tert-butylate 、 三(二甲胺基)膦 、 三氯化磷 作用下， 以 四氢呋喃 、 吡啶 、 水 、 乙腈 、 苯 为溶剂， 反应 151.0h， 生成 (S,S,S)-azaphosphatrane oxide
  参考文献：
  名称：

  P[(S,S,S)-PhHMeCNCH₂CH₂]₃N:  A New Chiral ³¹P and ¹H NMR Spectroscopic Reagent for the Direct Determination of ee Values of Chiral Azides

  摘要：

  A facile and economical procedure for the synthesis of the C-3 chiral alpha-phenylethylamino trisaminoamine [(S,S,S)-PhHMeCNHCH2CH2](3)N in good yield is reported. The corresponding bicyclic proazaphosphatrane P[(S,S,S)-PhHMeCNCH2CH2](3)N, its bicydic phosphoryl derivative, and its tricyclic P-protonated azaphosphatrane were also synthesized and characterized. It is found that the proazaphosphatrane is an efficient derivatizing agent for the direct determination of enantiomeric ratios of chiral azides by means of (31)p and H-1 NMR spectroscopy.

  DOI：

  10.1021/jo991304a

文献信息

• P[(<i>S</i>,<i>S</i>,<i>S</i>)-PhHMeCNCH₂CH₂]₃N:  A New Chiral ³¹P and ¹H NMR Spectroscopic Reagent for the Direct Determination of <i>e</i><i>e</i> Values of Chiral Azides
  作者：Xiaodong Liu、Palanichamy Ilankumaran、Ilia A. Guzei、John G. Verkade

  DOI：10.1021/jo991304a

  日期：2000.2.1

  A facile and economical procedure for the synthesis of the C-3 chiral alpha-phenylethylamino trisaminoamine [(S,S,S)-PhHMeCNHCH2CH2](3)N in good yield is reported. The corresponding bicyclic proazaphosphatrane P[(S,S,S)-PhHMeCNCH2CH2](3)N, its bicydic phosphoryl derivative, and its tricyclic P-protonated azaphosphatrane were also synthesized and characterized. It is found that the proazaphosphatrane is an efficient derivatizing agent for the direct determination of enantiomeric ratios of chiral azides by means of (31)p and H-1 NMR spectroscopy.