(3aS,7aS)-2-oxido-1,3-bis[(1S)-1-phenylethyl]-3a,4,5,6,7,7a-hexahydro-2H-benzo[d][1,3,2]diazaphosphol-2-ium | 745829-15-6

• 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: (3aS,7aS)-2-oxido-1,3-bis[(1S)-1-phenylethyl]-3a,4,5,6,7,7a-hexahydro-2H-benzo[d][1,3,2]diazaphosphol-2-ium
• CAS: 745829-15-6
• 化学式: C₂₂H₂₉N₂OP
• 分子量: 368.459
• InChiKey: AIRDFZVSXHRPMJ-GPHNJDIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (3aS,7aS)-2-oxido-1,3-bis[(1S)-1-phenylethyl]-3a,4,5,6,7,7a-hexahydro-2H-benzo[d][1,3,2]diazaphosphol-2-ium 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以65%的产率得到(3aS,7aS)-1-{2-oxo-1,3-bis[(S)-1-phenylethyl]perhydro-1,3,2λ⁵-benzodiazaphosphol-2-yl}-1-phenylmethanol
  参考文献：
  名称：

  (3aS,7aS)-1-{2-Oxo-1,3-bis[(S)-1-phenylethyl]perhydro-1,3,2λ⁵-benzodiazaphosphol-2-yl}-1-phenylmethanol: a mixture of diastereoisomers in a disordered crystal

  摘要：

  In the title compound, C29H35N2O2P, the stereogenic C center alpha to the P atom, formed during the Pudovik condensation reaction between a deprotonated chiral diazaphosphole and benzaldehyde, has disordered substituents, giving a mixture of Calpha-R and Calpha-S diastereoisomers. Moreover, this compound crystallizes with two independent molecules in the asymmetric unit. The observed configuration at the Calpha atom is 0.741 (6)-S mixed with 0.259 (6)-R, indicating diastereoisomeric enrichment during crystallization. Data from solution and solid-state studies consistently point to an epimerization process at the Calpha atom.

  DOI：

  10.1107/s0108270104008492
• 作为产物：
  描述：

  (1S,2S,1'S,1"S)-trans-N,N'-bis[(S)-α-phenylethyl]-1,2-diaminocyclohexane 在 三乙胺 、 三氯化磷 、 水 作用下， 以 甲苯 为溶剂， 生成 (3aS,7aS)-2-oxido-1,3-bis[(1S)-1-phenylethyl]-3a,4,5,6,7,7a-hexahydro-2H-benzo[d][1,3,2]diazaphosphol-2-ium
  参考文献：
  名称：

  Diastereoselective carbonyl phosphonylation using chiral N,N′-bis-[(S)-α-phenylethyl]-bicyclic phosphorous acid diamides

  摘要：

  Addition of aldehydes to the P-anion derivatives of chiral phosphorous acid diamides (1S,2S,1'S,1"S)-2 and (1R, 2R,1'S,1"S)-2 in THF gave alpha-hydroxyphosphonamides in good yield (64-100%) and moderate diastereoselectivities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.027

文献信息

• (3a<i>S</i>,7a<i>S</i>)-1-{2-Oxo-1,3-bis[(<i>S</i>)-1-phenylethyl]perhydro-1,3,2λ⁵-benzodiazaphosphol-2-yl}-1-phenylmethanol: a mixture of diastereoisomers in a disordered crystal
  作者：Gloria E. Moreno、Leticia Quintero、Sylvain Bernès、Cecilia Anaya de Parrodi

  DOI：10.1107/s0108270104008492

  日期：2004.6.15

  In the title compound, C29H35N2O2P, the stereogenic C center alpha to the P atom, formed during the Pudovik condensation reaction between a deprotonated chiral diazaphosphole and benzaldehyde, has disordered substituents, giving a mixture of Calpha-R and Calpha-S diastereoisomers. Moreover, this compound crystallizes with two independent molecules in the asymmetric unit. The observed configuration at the Calpha atom is 0.741 (6)-S mixed with 0.259 (6)-R, indicating diastereoisomeric enrichment during crystallization. Data from solution and solid-state studies consistently point to an epimerization process at the Calpha atom.
• Diastereoselective carbonyl phosphonylation using chiral N,N′-bis-[(S)-α-phenylethyl]-bicyclic phosphorous acid diamides
  作者：Gloria E. Moreno、Leticia Quintero、Sylvain Bernès、Cecilia Anaya de Parrodi

  DOI：10.1016/j.tetlet.2004.04.027

  日期：2004.5

  Addition of aldehydes to the P-anion derivatives of chiral phosphorous acid diamides (1S,2S,1'S,1"S)-2 and (1R, 2R,1'S,1"S)-2 in THF gave alpha-hydroxyphosphonamides in good yield (64-100%) and moderate diastereoselectivities. (C) 2004 Elsevier Ltd. All rights reserved.