N-[(R)-diphenylphosphoryl-(2-methylphenyl)methyl]tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-amine | 1282607-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: N-[(R)-diphenylphosphoryl-(2-methylphenyl)methyl]tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-amine
• CAS: 1282607-27-5
• 化学式: C₃₅H₃₀NOP
• 分子量: 511.603
• InChiKey: ZVURMVLXTYMHFQ-PGUFJCEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氨基-5H-二苯并(a,d)环庚烯 在 2C₄₈H₂₈O₄P^(1-)*Mg⁽²⁺⁾ 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-[(R)-diphenylphosphoryl-(2-methylphenyl)methyl]tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-amine
  参考文献：
  名称：

  Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched α-Amino Phosphine Oxides

  摘要：

  A new method to synthesize chiral alpha-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity.

  DOI：

  10.1021/ol200456y

文献信息

• Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched α-Amino Phosphine Oxides
  作者：Gajendrasingh K. Ingle、Yuxue Liang、Michael G. Mormino、Guilong Li、Frank R. Fronczek、Jon C. Antilla

  DOI：10.1021/ol200456y

  日期：2011.4.15

  A new method to synthesize chiral alpha-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity.