N-2-furoylallylglycine 4-tert-butylbenzyl thioester | 1361143-12-5

• 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-2-furoylallylglycine 4-tert-butylbenzyl thioester
• 英文别名: S-[(4-tert-butylphenyl)methyl] (2R)-2-(furan-2-carbonylamino)pent-4-enethioate
• CAS: 1361143-12-5
• 化学式: C₂₁H₂₅NO₃S
• 分子量: 371.5
• InChiKey: BFQXOKVHSJLGTG-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  DL-2-氨基-4-戊烯酸 在 (8S,9R)-6'-methoxy-9-(1-hydroxynaphtalen-2-yl)-cinchonan 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 120.0h， 生成 N-2-furoylallylglycine 4-tert-butylbenzyl thioester 、 N-2-furoylallylglycine 4-tert-butylbenzyl thioester
  参考文献：
  名称：

  The Dynamic Kinetic Resolution of Azlactones with Thiol Nucleophiles Catalyzed by Arylated, Deoxygenated Cinchona Alkaloids

  摘要：

  A significant improvement of the available organocatalytic methods (in terms of product substrate scope and product enantiomeric excess) for the generation of enantioenriched alpha-amino acid thioesters via the dynamic kinetic resolution of azlactones is reported. C-9 arylated cinchona alkaloid catalysts have been found to be considerably superior to other bifunctional alkaloid catalysts as the promoters of this asymmetric process.

  DOI：

  10.1021/jo202662d

文献信息

• The Dynamic Kinetic Resolution of Azlactones with Thiol Nucleophiles Catalyzed by Arylated, Deoxygenated Cinchona Alkaloids
  作者：Zaida Rodríguez-Docampo、Cormac Quigley、Sean Tallon、Stephen J. Connon

  DOI：10.1021/jo202662d

  日期：2012.3.2

  A significant improvement of the available organocatalytic methods (in terms of product substrate scope and product enantiomeric excess) for the generation of enantioenriched alpha-amino acid thioesters via the dynamic kinetic resolution of azlactones is reported. C-9 arylated cinchona alkaloid catalysts have been found to be considerably superior to other bifunctional alkaloid catalysts as the promoters of this asymmetric process.