(2S,3S)-N²,3-dimethyl-N¹-phenylpentane-1,2-diamine | 1430747-34-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3S)-N²,3-dimethyl-N¹-phenylpentane-1,2-diamine
• 英文别名: (2S,3S)-2-N,3-dimethyl-1-N-phenylpentane-1,2-diamine
• CAS: 1430747-34-4
• 化学式: C₁₃H₂₂N₂
• 分子量: 206.331
• InChiKey: SZQYAWNDECIWES-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N²,3-dimethyl-N¹-phenylpentane-1,2-diamine 在 三乙胺 、 三氯化磷 作用下， 以 甲苯 、 苯 为溶剂， 反应 1.08h， 生成 (4S)-4-sec-butyl-3-methyl-1-phenyl-2-(tricyclo[3.3.1.1.3′,7′]dec-1′-yloxy)-1,3,2-diazaphospholidine
  参考文献：
  名称：

  Development of P∗-monodentate diamidophosphites with a C1-symmetric 1,2-diamine backbone: the effects of substituents in the 1,3,2-diazaphospholidine cycle on Pd-catalyzed asymmetric allylations

  摘要：

  We have designed and synthesized a small library of modular monodentate diamidophosphite ligands with stereogenic phosphorus atoms. The library was prepared efficiently from the commercially available and inexpensive (S)-N-Boc-amino acids. These novel ligands were screened in the Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate with dimethyl malonate as the C-nucleophile with up to 93% ee being obtained. The results showed that the different substituents in the 1,3,2-diazaphospholidine cycle had remarkable effects on the enantioselectivity. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.010
• 作为产物：
  描述：

  tert-butyl (2S,3S)-3-methyl-1-oxo-1-(phenylamino)pentan-2-ylcarbamate 在 lithium aluminium tetrahydride 、 水 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以71%的产率得到(2S,3S)-N²,3-dimethyl-N¹-phenylpentane-1,2-diamine
  参考文献：
  名称：

  Development of P∗-monodentate diamidophosphites with a C1-symmetric 1,2-diamine backbone: the effects of substituents in the 1,3,2-diazaphospholidine cycle on Pd-catalyzed asymmetric allylations

  摘要：

  We have designed and synthesized a small library of modular monodentate diamidophosphite ligands with stereogenic phosphorus atoms. The library was prepared efficiently from the commercially available and inexpensive (S)-N-Boc-amino acids. These novel ligands were screened in the Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate with dimethyl malonate as the C-nucleophile with up to 93% ee being obtained. The results showed that the different substituents in the 1,3,2-diazaphospholidine cycle had remarkable effects on the enantioselectivity. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.010

文献信息

• Pd-Catalyzed asymmetric transformations involving P*-mono- and P*,N-bidentate diamidophosphites derived from (2S,3S)-N 2,3-dimethyl-N 1-phenylpentane-1,2-diamine
  作者：K. N. Gavrilov、I. V. Chuchelkin、S. V. Zheglov、A. A. Shiryaev、O. V. Potapova、I. M. Novikov、E. A. Rastorguev、P. V. Petrovskii、V. A. Davankov

  DOI：10.1007/s11172-012-0267-3

  日期：2012.10

  The synthesis of new P*-mono- and P*,N-bidentate diamidophosphites, containing 1,3,2-diazaphospholidine rings formed starting from (2S,3S)-N 2,3-dimethyl-N 1-phenylpentane-1,2-diamine, is described. Comparison of their efficiency in the Pd-catalyzed enantioselective allylation with (E)-1,3-diphenylallyl acetate showed that up to 97% ee was reached in the reaction involving dimethyl malonate as a C-nucleophile. The Pd-catalyzed desymmetrization of N,N′-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate gave up to 61% ee.

  描述了一种新型P*-单齿和P*,N-双齿二酰胺磷酸酯的合成，这些化合物包含从(2S,3S)-N 2,3-二甲基-N 1-苯基戊二胺出发形成的1,3,2-二氮基磷烯环。与(E)-1,3-二苯基丙烯酸乙酯的Pd催化选择性烯丙基化反应比较表明，在涉及二甲基美克酮作为C-亲核试剂的反应中，产物的对映体过量（ee）高达97%。Pd催化的N,N′-二托磺酰-美索-环戊-4-烯-1,3-二醇双氨基甲酸酯的去对称化反应得到的对映体过量最高可达61%。