2-(p-methoxyanilino)-2-oxo-5,5-dimethyl-1,3,2-oxazaphosphorinane | 136144-98-4

• 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: 2-(p-methoxyanilino)-2-oxo-5,5-dimethyl-1,3,2-oxazaphosphorinane
• 英文别名: N-(4-methoxyphenyl)-5,5-dimethyl-2-oxido-1,3,2-oxazaphosphinan-2-ium-2-amine
• CAS: 136144-98-4
• 化学式: C₁₂H₁₉N₂O₃P
• 分子量: 270.268
• InChiKey: YNOKZKRRRAOWAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲氧苯胺 在 三乙胺 、 三氯氧磷 作用下， 以 乙酸乙酯 为溶剂， 反应 192.0h， 生成 2-(p-methoxyanilino)-2-oxo-5,5-dimethyl-1,3,2-oxazaphosphorinane
  参考文献：
  名称：

  Anomeric-like substituent effects on the chair-chair conformational equilibrium of the 2-oxo-1,3,2-oxazaphosphorinane ring system

  摘要：

  The chair-chair equilibria for a series of 5,5-dimethyl-2-oxo-(2-p-X-anilino)-1,3,2-oxazaphosphorinanes were determined by H-1 NMR. The percentage of chair conformer with the p-X-anilino group axial is increased by the presence of electron withdrawing X, while the opposite is true for electron-donor para X. Reasonably good linear plots of log K vs sigma-p were obtained in the solvents acetone-d6, CD3CN, and CD3NO2 with rho = 0.28-0.36. These results are interpreted in terms of the dominance of the endo anomeric effect involving overlap of the endocyclic N(3) and O(1) p lone pairs with the axial P-N sigma* orbital (p-XC6H4NHP).

  DOI：

  10.1021/jo00021a031

文献信息

• Anomeric-like substituent effects on the chair-chair conformational equilibrium of the 2-oxo-1,3,2-oxazaphosphorinane ring system
  作者：Wesley G. Bentrude、William N. Setzer、Emmanuel Ramli、Mamunur Khan、Alan E. Sopchik

  DOI：10.1021/jo00021a031

  日期：1991.10

  The chair-chair equilibria for a series of 5,5-dimethyl-2-oxo-(2-p-X-anilino)-1,3,2-oxazaphosphorinanes were determined by H-1 NMR. The percentage of chair conformer with the p-X-anilino group axial is increased by the presence of electron withdrawing X, while the opposite is true for electron-donor para X. Reasonably good linear plots of log K vs sigma-p were obtained in the solvents acetone-d6, CD3CN, and CD3NO2 with rho = 0.28-0.36. These results are interpreted in terms of the dominance of the endo anomeric effect involving overlap of the endocyclic N(3) and O(1) p lone pairs with the axial P-N sigma* orbital (p-XC6H4NHP).