benzyl (R)-2-(N-allyl-4-methylbenzenesulfonamido)-1-phenylethylcarbamate | 1007121-82-5

• 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 (R)-2-(N-allyl-4-methylbenzenesulfonamido)-1-phenylethylcarbamate
• 英文别名: benzyl N-[(1R)-2-[(4-methylphenyl)sulfonyl-prop-2-enylamino]-1-phenylethyl]carbamate
• CAS: 1007121-82-5
• 化学式: C₂₆H₂₈N₂O₄S
• 分子量: 464.585
• InChiKey: YKNDUWHHWLYVSZ-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (R)-2-(N-allyl-4-methylbenzenesulfonamido)-1-phenylethylcarbamate 在 (2,6-bis(diphenylphosphinomethyl)pyridine)dichloropalladium silver tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 benzyl (2R,6R)-2-methyl-6-phenyl-4-(4-methylbenzenesulfonyl)piperazine-1-carboxylate 、 benzyl (2S,6R)-2-methyl-6-phenyl-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
• 作为产物：
  描述：

  (R)-3-(benzyloxycarbonyl)-4-phenyl-[1,2,3]oxathiazolidine 2,2-dioxide 、 N-烯丙基对甲苯磺酰胺 在 氢氧化钾 、 盐酸 作用下， 以 乙腈 、 乙酸乙酯 为溶剂， 以89%的产率得到benzyl (R)-2-(N-allyl-4-methylbenzenesulfonamido)-1-phenylethylcarbamate
  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