N-<2-Methyl-1-<(triphenylmethyl)amino>-2-propyl>-L-alanine methyl ester | 170033-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-<2-Methyl-1-<(triphenylmethyl)amino>-2-propyl>-L-alanine methyl ester
• 英文别名: methyl (2S)-2-[[2-methyl-1-(tritylamino)propan-2-yl]amino]propanoate
• CAS: 170033-60-0
• 化学式: C₂₇H₃₂N₂O₂
• 分子量: 416.563
• InChiKey: MTAOAJSVQKFBBC-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<2-Methyl-1-<(triphenylmethyl)amino>-2-propyl>-L-alanine methyl ester 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-2,2,6-Trimethylpiperazine dihydrochloride
  参考文献：
  名称：

  Asymmetric Synthesis of 2,6-Methylated Piperazines

  摘要：

  The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step. The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intramolecular Mitsunobu reaction to set the required stereochemistry. The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6-trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction. These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.

  DOI：

  10.1021/jo00118a039
• 作为产物：
  描述：

  (R)-2-trifluoromethanesulfonyloxy-propionic acid methyl ester 、 2-Methyl-1-<(triphenylmethyl)amino>-2-aminopropane 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到N-<2-Methyl-1-<(triphenylmethyl)amino>-2-propyl>-L-alanine methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of 2,6-Methylated Piperazines

  摘要：

  The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step. The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intramolecular Mitsunobu reaction to set the required stereochemistry. The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6-trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction. These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.

  DOI：

  10.1021/jo00118a039

文献信息

• Asymmetric Synthesis of 2,6-Methylated Piperazines
  作者：John W. Mickelson、Kenneth L. Belonga、E. Jon Jacobsen

  DOI：10.1021/jo00118a039

  日期：1995.6

  The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step. The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intramolecular Mitsunobu reaction to set the required stereochemistry. The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6-trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction. These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.