(9H-fluoren-9-yl)methyl (S)-1-formamido-3-phenylpropan-2-ylcarbamate | 1095037-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl (S)-1-formamido-3-phenylpropan-2-ylcarbamate
• 英文别名: Fmoc-Phe-Ψ[CH2-NHCHO]；9H-fluoren-9-ylmethyl N-[(2S)-1-formamido-3-phenylpropan-2-yl]carbamate
• CAS: 1095037-60-7
• 化学式: C₂₅H₂₄N₂O₃
• 分子量: 400.477
• InChiKey: QNYWVCHPLOHKLN-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl (S)-1-formamido-3-phenylpropan-2-ylcarbamate 在 伯吉斯试剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 methyl ((R)-1-(2-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropyl)amino)-2-oxoethyl)-4-oxoazetidine-2-carbonyl)-L-alaninate
  参考文献：
  名称：

  Synthesis of β-lactam peptidomimetics through Ugi MCR: first application of chiral Nβ-Fmoc amino alkyl isonitriles in MCRs

  摘要：

  Chiral N-beta-Fmoc amino alkyl isonitriles were employed in Ugi multi component reactions (Ugi 4C-3CR) to obtain functionalized beta-lactam peptidomimetics with L-aspartic acid alpha-methyl ester/peptide ester and organic aldehydes. The reactions were carried out in MeOH. Thirteen Ugi products have been prepared in good to moderate yields with good diastereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.090
• 作为产物：
  描述：

  Fmoc-L-beta-高苯丙氨酸 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (9H-fluoren-9-yl)methyl (S)-1-formamido-3-phenylpropan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis of β-lactam peptidomimetics through Ugi MCR: first application of chiral Nβ-Fmoc amino alkyl isonitriles in MCRs

  摘要：

  Chiral N-beta-Fmoc amino alkyl isonitriles were employed in Ugi multi component reactions (Ugi 4C-3CR) to obtain functionalized beta-lactam peptidomimetics with L-aspartic acid alpha-methyl ester/peptide ester and organic aldehydes. The reactions were carried out in MeOH. Thirteen Ugi products have been prepared in good to moderate yields with good diastereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.090

文献信息

• Chiral <i>N</i>-Fmoc-β-Amino Alkyl Isonitriles Derived from Amino Acids: First Synthesis and Application in 1-Substituted Tetrazole Synthesis
  作者：Vommina V. Sureshbabu、N. Narendra、G. Nagendra

  DOI：10.1021/jo801527d

  日期：2009.1.2

  A novel class of optically active N-Fmoc-protected amino isonitriles has been described for the first time. Conversion of the carboxyl group of Fmoc-β-amino acids into an isocyano group has resulted in a new class of N-urethane-protected amino isonitriles. All the isonitriles have been isolated as stable solids, purified, and completely characterized. A synthetic application of the obtained isonitriles

  首次描述了一类新型的具有光学活性的N -Fmoc保护的氨基异腈。Fmoc-β-氨基酸的羧基转化为异氰基导致了新型的N-氨基甲酸酯保护的氨基异腈。所有的异腈均已分离为稳定的固体，经过纯化并进行了完全鉴定。通过与三甲基甲硅烷基叠氮化物通过2 + 3环加成反应合成氨基酸的1-取代的四唑类似物，也证明了所获得的异腈的合成应用。
• Cyanogen Bromide as Dehydrosulfurizing Agent for the Synthesis of Nβ-Fmoc-Amino Alkyl Isonitriles from Nβ-Fmoc-Amino Alkyl Thioformamides
  作者：V. Sureshbabu、T. Vishwanatha、H. Hemantha

  DOI：10.1055/s-0029-1219583

  日期：2010.4

  Synthetically useful NI²-Fmoc amino alkyl isonitriles are prepared conveniently from NI²-Fmoc amino alkyl thioformamides via a cyanogen bromide mediated dehydrosulfurization. The reaction is fast, clean, and yields are good. © Georg Thieme Verlag Stuttgart - New York.

  合成有用的NI 2 -Fmoc氨基烷基异腈可以方便地从NI 2 -Fmoc氨基烷基硫代甲酰胺通过溴化氰介导的脱硫脱硫来制备。反应快速、清洁、收率良好。© Georg Thieme Verlag 斯图加特 - 纽约。
• Synthesis of β-lactam peptidomimetics through Ugi MCR: first application of chiral Nβ-Fmoc amino alkyl isonitriles in MCRs
  作者：T.M. Vishwanatha、N. Narendra、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2011.08.090

  日期：2011.10

  Chiral N-beta-Fmoc amino alkyl isonitriles were employed in Ugi multi component reactions (Ugi 4C-3CR) to obtain functionalized beta-lactam peptidomimetics with L-aspartic acid alpha-methyl ester/peptide ester and organic aldehydes. The reactions were carried out in MeOH. Thirteen Ugi products have been prepared in good to moderate yields with good diastereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.