2-Benzyloxycarbonylamino-4-carbamoyl-4,4-difluoro-butyric acid tert-butyl ester | 175548-89-7

• 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: 2-Benzyloxycarbonylamino-4-carbamoyl-4,4-difluoro-butyric acid tert-butyl ester
• 英文别名: Tert-butyl 5-amino-4,4-difluoro-5-oxo-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 175548-89-7
• 化学式: C₁₇H₂₂F₂N₂O₅
• 分子量: 372.369
• InChiKey: PPPHEEWIVDYTQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Benzyloxycarbonylamino-4-carbamoyl-4,4-difluoro-butyric acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 生成 2,5-diamino-4,4-difluoro-5-oxopentanoic acid
  参考文献：
  名称：

  Facile Synthesis of dl-4,4-Difluoroornithine, dl-4,4-Difluoroglutamine, and γ-dl-4,4-Difluoroglutamyl-Containing Peptides:  Regiospecific Addition of Nucleophiles to N-Cbz-di-tert-butyl-dl-4,4-difluoroglutamate

  摘要：

  The reaction of several nucleophiles with N-Cbz-protected di-tert-butyl-DL-4,4-difluoroglutamate was investigated as an approach to the synthesis of various fluorinated amino acids and peptides. The gamma-carboxyl group is highly activated by the two adjacent fluorine atoms, and nucleophilic reactions occurred exclusively at that carbonyl carbon. Further transformations of the reaction pro ducts re suited in the synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and gamma-DL-4,4-difluoroglutamyl-containing dipeptides.

  DOI：

  10.1021/jo952044+
• 作为产物：
  描述：

  4,4-二氟-DL-谷氨酸 在 硫酸 、 氨 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 136.0h， 生成 2-Benzyloxycarbonylamino-4-carbamoyl-4,4-difluoro-butyric acid tert-butyl ester
  参考文献：
  名称：

  Facile Synthesis of dl-4,4-Difluoroornithine, dl-4,4-Difluoroglutamine, and γ-dl-4,4-Difluoroglutamyl-Containing Peptides:  Regiospecific Addition of Nucleophiles to N-Cbz-di-tert-butyl-dl-4,4-difluoroglutamate

  摘要：

  The reaction of several nucleophiles with N-Cbz-protected di-tert-butyl-DL-4,4-difluoroglutamate was investigated as an approach to the synthesis of various fluorinated amino acids and peptides. The gamma-carboxyl group is highly activated by the two adjacent fluorine atoms, and nucleophilic reactions occurred exclusively at that carbonyl carbon. Further transformations of the reaction pro ducts re suited in the synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and gamma-DL-4,4-difluoroglutamyl-containing dipeptides.

  DOI：

  10.1021/jo952044+