(1R,2R)-N1-isopropyl-N1-methyl-1,2-diphenylethane-1,2-diamine | 1558718-96-9

• 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: (1R,2R)-N1-isopropyl-N1-methyl-1,2-diphenylethane-1,2-diamine
• CAS: 1558718-96-9
• 化学式: C₁₈H₂₄N₂
• 分子量: 268.402
• InChiKey: GXOHNNKCEZISSD-QZTJIDSGSA-N

物化性质

• 沸点：
  350.2±30.0 °C(predicted)
• 密度：
  1.025±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  苯膦酰二氯 、 (1R,2R)-N1-isopropyl-N1-methyl-1,2-diphenylethane-1,2-diamine 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以62%的产率得到[(1R,2R)-2-[methyl(propan-2-yl)amino]-1,2-diphenylethyl]({[(1R,2R)-2-[methyl(propan-2-yl)amino]-1,2-diphenylethyl]amino}(phenyl)thiophosphoryl)amine
  参考文献：
  名称：

  Enantioselectivity switch controlled by N,N′-di- or N,N,N′,N′-tetra-substituted chiral thiophosphorodiamide ligands, structural relatives of thioureas, in catalytic additions of diethylzinc to aldehydes

  摘要：

  We have developed a series of new chiral thiophosphorodiamide ligands derived from (1R,2R)-(+)-1,2-diphenylethylenediamine, which are the structural relatives of thioureas. An investigation into their catalytic properties in asymmetric additions of diethylzinc to aldehydes has shown that N,N,N',N'-tetra-substituted chiral thiophosphorodiamides can give (R)-secondary alcohols with up to 98% yield and 98% ee, while N,N'-di-substituted chiral thiophosphorodiamides give (S)-secondary alcohols with up to 99% yield and 97% ee values. The enantioselectivity switch is highly efficient with a broad substrate scope. We have also proposed hypothetical reaction pathways, which result in an enantioselectivity switch. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.014
• 作为产物：
  描述：

  在 甲酸 、 potassium carbonate 、 一水合肼 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.0h， 生成 (1R,2R)-N1-isopropyl-N1-methyl-1,2-diphenylethane-1,2-diamine
  参考文献：
  名称：

  Enantioselectivity switch controlled by N,N′-di- or N,N,N′,N′-tetra-substituted chiral thiophosphorodiamide ligands, structural relatives of thioureas, in catalytic additions of diethylzinc to aldehydes

  摘要：

  We have developed a series of new chiral thiophosphorodiamide ligands derived from (1R,2R)-(+)-1,2-diphenylethylenediamine, which are the structural relatives of thioureas. An investigation into their catalytic properties in asymmetric additions of diethylzinc to aldehydes has shown that N,N,N',N'-tetra-substituted chiral thiophosphorodiamides can give (R)-secondary alcohols with up to 98% yield and 98% ee, while N,N'-di-substituted chiral thiophosphorodiamides give (S)-secondary alcohols with up to 99% yield and 97% ee values. The enantioselectivity switch is highly efficient with a broad substrate scope. We have also proposed hypothetical reaction pathways, which result in an enantioselectivity switch. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.014