(S)-(9H-fluoren-9-yl)methyl (1-diazo-2-oxohex-5-yn-3-yl)carbamate | 1417532-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-(9H-fluoren-9-yl)methyl (1-diazo-2-oxohex-5-yn-3-yl)carbamate
• 英文别名: Fmoc-L-Pra-ketene；9H-fluoren-9-ylmethyl N-[(3S)-1-diazo-2-oxohex-5-yn-3-yl]carbamate
• CAS: 1417532-33-2
• 化学式: C₂₁H₁₇N₃O₃
• 分子量: 359.384
• InChiKey: AZALFZIOUNUOON-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(9H-fluoren-9-yl)methyl (1-diazo-2-oxohex-5-yn-3-yl)carbamate 在 silver trifluoroacetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以60%的产率得到FMOC-S-3-氨基-5-己炔酸
  参考文献：
  名称：

  Azide- and Alkyne-Functionalised α- and β3-Amino Acids

  摘要：

  The synthesis and full characterisation of bifunctional beta(3)-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing beta(3)-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding alpha-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis.

  DOI：

  10.1055/s-0032-1317445
• 作为产物：
  描述：

  Fmoc-L-炔丙基甘氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 、 重氮甲烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 以39%的产率得到(S)-(9H-fluoren-9-yl)methyl (1-diazo-2-oxohex-5-yn-3-yl)carbamate
  参考文献：
  名称：

  Azide- and Alkyne-Functionalised α- and β3-Amino Acids

  摘要：

  The synthesis and full characterisation of bifunctional beta(3)-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing beta(3)-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding alpha-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis.

  DOI：

  10.1055/s-0032-1317445

文献信息

• Azide- and Alkyne-Functionalised α- and β3-Amino Acids
  作者：Daniel Pedersen、Tjerk Sminia

  DOI：10.1055/s-0032-1317445

  日期：——

  The synthesis and full characterisation of bifunctional beta(3)-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing beta(3)-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding alpha-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis.