N-tosyl-L-phenylalanine | 86069-64-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-tosyl-L-phenylalanine
• 英文别名: (2S)-2-[(4-methylphenyl)sulfonylamino]-3-phenylpropanamide
• CAS: 86069-64-9
• 化学式: C₁₆H₁₈N₂O₃S
• 分子量: 318.397
• InChiKey: OZRBXXXXHHQBCE-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tosyl-L-phenylalanine 在 palladium diacetate 、 1,2-双(二苯基膦)乙烷 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (S)-1,3-Dibenzyl-4-(toluene-4-sulfonyl)-5-vinyl-piperazin-2-one
  参考文献：
  名称：

  A new access to 3,5-disubstituted piperazinones via Pd(0)-catalyzed amination

  摘要：

  An original synthetic route toward 3,5-disubstituted piperazinones has been developed. The method relies upon a 6-exo intramolecular process between a sulfonylated nitrogen atom of amino acid derivation and an eta(3)-allyl-palladium moiety. This cyclization process generates the two possible (cis and trans) diastereoisomers whose ratio depends on the amino acid employed. The bulkier the amino acid residue, the higher the observed cis:trans ratio. Convincing evidence for reversible intramolecular addition of the nitrogen nucleophile to the eta(3)-allyl-palladium complex is put forward. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00885-2
• 作为产物：
  描述：

  L-苯丙氨酸 、 对甲苯磺酰氯 在 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 生成 N-tosyl-L-phenylalanine
  参考文献：
  名称：

  A new access to 3,5-disubstituted piperazinones via Pd(0)-catalyzed amination

  摘要：

  An original synthetic route toward 3,5-disubstituted piperazinones has been developed. The method relies upon a 6-exo intramolecular process between a sulfonylated nitrogen atom of amino acid derivation and an eta(3)-allyl-palladium moiety. This cyclization process generates the two possible (cis and trans) diastereoisomers whose ratio depends on the amino acid employed. The bulkier the amino acid residue, the higher the observed cis:trans ratio. Convincing evidence for reversible intramolecular addition of the nitrogen nucleophile to the eta(3)-allyl-palladium complex is put forward. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00885-2

文献信息

• A new access to 3,5-disubstituted piperazinones via Pd(0)-catalyzed amination
  作者：Benoit Ferber、Sébastien Lemaire、Mary M. Mader、Guillaume Prestat、Giovanni Poli

  DOI：10.1016/s0040-4039(03)00885-2

  日期：2003.5

  An original synthetic route toward 3,5-disubstituted piperazinones has been developed. The method relies upon a 6-exo intramolecular process between a sulfonylated nitrogen atom of amino acid derivation and an eta(3)-allyl-palladium moiety. This cyclization process generates the two possible (cis and trans) diastereoisomers whose ratio depends on the amino acid employed. The bulkier the amino acid residue, the higher the observed cis:trans ratio. Convincing evidence for reversible intramolecular addition of the nitrogen nucleophile to the eta(3)-allyl-palladium complex is put forward. (C) 2003 Elsevier Science Ltd. All rights reserved.