benzyl 2-methyl-4-(4-methylbenzenesulfonyl)piperazine-1-carboxylate | 1007121-64-3

• 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: benzyl 2-methyl-4-(4-methylbenzenesulfonyl)piperazine-1-carboxylate
• 英文别名: Benzyl 2-methyl-4-(4-methylphenyl)sulfonylpiperazine-1-carboxylate；benzyl 2-methyl-4-(4-methylphenyl)sulfonylpiperazine-1-carboxylate
• CAS: 1007121-64-3
• 化学式: C₂₀H₂₄N₂O₄S
• 分子量: 388.488
• InChiKey: SQLSTYWHPIVDEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  benzyl 2-(N-allyl-4-methylbenzenesulfonamido)ethylcarbamate 在 (2,6-bis(diphenylphosphinomethyl)pyridine)dichloropalladium silver tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以89%的产率得到benzyl 2-methyl-4-(4-methylbenzenesulfonyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction

  摘要：

  A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A(1,3) strain.

  DOI：

  10.1021/ol702891p