benzyl 2-(N-allyl-4-methylbenzenesulfonamido)ethylcarbamate | 1007121-63-2

• 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-(N-allyl-4-methylbenzenesulfonamido)ethylcarbamate
• 英文别名: benzyl 2-(N-allyl-4-methylphenylsulfonamido)ethylcarbamate；benzyl N-[2-[(4-methylphenyl)sulfonyl-prop-2-enylamino]ethyl]carbamate
• CAS: 1007121-63-2
• 化学式: C₂₀H₂₄N₂O₄S
• 分子量: 388.488
• InChiKey: QRMNFJAIFSIMKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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 2-(N-allyl-4-methylbenzenesulfonamido)ethylcarbamate 在 双(乙腈)氯化钯(II) 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 36.0h， 以91%的产率得到7-(toluene-4-sulfonyl)-tetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular Chloroamination of Alkenes

  摘要：

  A mild and facile Pd-catalyzed intramolecular chloroamination of unactivated alkenes has been described. This reaction takes place at room temperature and is tolerant of synthetically useful acid-sensitive functional groups. Generally high exo-selectivities are observed in the formation of a variety of 5- and 6-membered rings. This system is unique in its ability to tolerate multidentate ligands on palladium, which opens up the possibility of controlling the absolute sense of induction using a chiral ligand.

  DOI：

  10.1021/ol702922c
• 作为产物：
  描述：

  N-allyl-N'-carbobenzoxyethylenediamine 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 20.0h， 以53%的产率得到benzyl 2-(N-allyl-4-methylbenzenesulfonamido)ethylcarbamate
  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