(1R,2R)-1-N-(diphenylphosphoroso)-2-N-(propan-2-yl)cyclohexane-1,2-diamine | 1408252-81-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R)-1-N-(diphenylphosphoroso)-2-N-(propan-2-yl)cyclohexane-1,2-diamine
• 英文别名: (1R,2R)-1-N-(diphenylphosphoryl)-2-N-(propan-2-yl)-cyclohexane-1,2-diamine；(1R,2R)-2-N-diphenylphosphoryl-1-N-propan-2-ylcyclohexane-1,2-diamine
• CAS: 1408252-81-2
• 化学式: C₂₁H₂₉N₂OP
• 分子量: 356.448
• InChiKey: OIWYKGWZNGGGEB-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-((1R,2R)-2-aminocyclohexyl)isoindoline-1,3-dione 在 potassium carbonate 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.17h， 生成 (1R,2R)-1-N-(diphenylphosphoroso)-2-N-(propan-2-yl)cyclohexane-1,2-diamine
  参考文献：
  名称：

  Constructing a Quantitative Correlation between N-Substituent Sizes of Chiral Ligands and Enantioselectivities in Asymmetric Addition Reactions of Diethylzinc with Benzaldehyde

  摘要：

  Using the asymmetric addition reaction of diethylzinc with benzylaldehyde as a model, we have demonstrated that excellent correlations exist between steric reference parameters (Charton and Sterimol values) for appropriate sets of substituents present on chiral 1,2-aminophosphoramide ligands and the enantiomeric ratios of alcohol products produced in this process.

  DOI：

  10.1021/jo3016715
• 作为试剂：
  描述：

  2-噻吩甲醛 、 diethylzinc 在 (1R,2R)-1-N-(diphenylphosphoroso)-2-N-(propan-2-yl)cyclohexane-1,2-diamine 、 四丁基溴化铵 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 6.5h， 以98%的产率得到(1R)-1-(thiophen-2-yl)propan-1-ol
  参考文献：
  名称：

  Synergistic effect of achiral quaternary ammonium salt on asymmetric additions of diethylzinc to aldehydes

  摘要：

  Our investigation has shown that achiral quaternary ammonium salt has a significant synergistic effect on the asymmetric additions of diethylzinc to aldehydes catalyzed by chiral phosphoramide-Zn(II) complex. The addition of 10 mol % NBu4X can dramatically reduce the loading amount of chiral ligand without sacrificing the excellent reactivity and enantioselectivity of the asymmetric reaction. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.066

文献信息

• Constructing a Quantitative Correlation between N-Substituent Sizes of Chiral Ligands and Enantioselectivities in Asymmetric Addition Reactions of Diethylzinc with Benzaldehyde
  作者：Huayin Huang、Hua Zong、Guangling Bian、Ling Song

  DOI：10.1021/jo3016715

  日期：2012.11.16

  Using the asymmetric addition reaction of diethylzinc with benzylaldehyde as a model, we have demonstrated that excellent correlations exist between steric reference parameters (Charton and Sterimol values) for appropriate sets of substituents present on chiral 1,2-aminophosphoramide ligands and the enantiomeric ratios of alcohol products produced in this process.