(4-Nitrophenyl) 2-[bis(1-adamantyloxycarbonyl)amino]acetate | 148797-77-7

• 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: (4-Nitrophenyl) 2-[bis(1-adamantyloxycarbonyl)amino]acetate
• CAS: 148797-77-7
• 化学式: C₃₀H₃₆N₂O₈
• 分子量: 552.624
• InChiKey: GQJJUERUDMZYFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  H-Gly-Phe-Leu-OBzl 、 (4-Nitrophenyl) 2-[bis(1-adamantyloxycarbonyl)amino]acetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以63%的产率得到Adoc2-Gly-Gly-Phe-Leu-OBzl
  参考文献：
  名称：

  Synthesis and Application of N,N-Bis-(1-adamantyloxycarbonyl) Amino Acids.

  摘要：

  The preparation of novel bis-(1-adamantyloxycarbonyl) amino acid derivatives has been undertaken and their properties studied. Among them, the p-nitrophenyl esters were subsequently applied to the stepwise synthesis of Leu-enkephalin. In the last coupling step, some hydantoin formation was encountered but it could be nearly completely overcome by working with more concentrated solution. The preparation of a tyrosine derivative presented special problems owing to the existence of the phenolic group in the precursor. The relative stability of 1-adamantyloxycarbonyl as N- and O-protecting groups was also studied.

  DOI：

  10.3891/acta.chem.scand.47-0374
• 作为产物：
  描述：

  1-氯甲酰氧基金刚烷 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 、 乙腈 为溶剂， 反应 30.0h， 生成 (4-Nitrophenyl) 2-[bis(1-adamantyloxycarbonyl)amino]acetate
  参考文献：
  名称：

  Synthesis and Application of N,N-Bis-(1-adamantyloxycarbonyl) Amino Acids.

  摘要：

  The preparation of novel bis-(1-adamantyloxycarbonyl) amino acid derivatives has been undertaken and their properties studied. Among them, the p-nitrophenyl esters were subsequently applied to the stepwise synthesis of Leu-enkephalin. In the last coupling step, some hydantoin formation was encountered but it could be nearly completely overcome by working with more concentrated solution. The preparation of a tyrosine derivative presented special problems owing to the existence of the phenolic group in the precursor. The relative stability of 1-adamantyloxycarbonyl as N- and O-protecting groups was also studied.

  DOI：

  10.3891/acta.chem.scand.47-0374

文献信息

• Synthesis and Application of N,N-Bis-(1-adamantyloxycarbonyl) Amino Acids.
  作者：Barthélémy Nyasse、Ulf Ragnarsson、Jukka Jokisaari、Risto S. Laitinen、Jon Brunvoll、Jens Spanget-Larsen、Radka K. MIlanova、Hiroyuki Nakata、Ahmad Nasiri、Yoshito Okada

  DOI：10.3891/acta.chem.scand.47-0374

  日期：——

  The preparation of novel bis-(1-adamantyloxycarbonyl) amino acid derivatives has been undertaken and their properties studied. Among them, the p-nitrophenyl esters were subsequently applied to the stepwise synthesis of Leu-enkephalin. In the last coupling step, some hydantoin formation was encountered but it could be nearly completely overcome by working with more concentrated solution. The preparation of a tyrosine derivative presented special problems owing to the existence of the phenolic group in the precursor. The relative stability of 1-adamantyloxycarbonyl as N- and O-protecting groups was also studied.