(9H-fluoren-9-yl)methyl (S)-1-isocyano-3-methylbutan-2-ylcarbamate | 1095037-86-7

• 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-isocyano-3-methylbutan-2-ylcarbamate
• 英文别名: Fmoc-Val-Ψ[CH2-NC]；9H-fluoren-9-ylmethyl N-[(2S)-1-isocyano-3-methylbutan-2-yl]carbamate
• CAS: 1095037-86-7
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: YQBNYSVBYHDOOD-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl (S)-1-isocyano-3-methylbutan-2-ylcarbamate 在 叠氮基三甲基硅烷 、 zinc dibromide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以87%的产率得到(9H-fluoren-9-yl)methyl (S)-3-methyl-1-(1H-tetrazol-1-yl)butan-2-ylcarbamate
  参考文献：
  名称：

  衍生自氨基酸的手性N -Fmoc-β-氨基烷基异腈：首次合成及其在1-取代的四唑合成中的应用

  摘要：

  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。

  DOI：

  10.1021/jo801527d
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 甲酸 、 伯吉斯试剂 作用下， 以 二氯甲烷 为溶剂， 生成 (9H-fluoren-9-yl)methyl (S)-1-isocyano-3-methylbutan-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

• Synthesis of novel glycopeptidomimetics via Nβ-protected-amino alkyl isonitrile based Ugi 4C reaction
  作者：Basavalingappa Vasantha、Girish Prabhu、Hosmani Basavaprabhu、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2013.06.013

  日期：2013.8

  The Ugi-4C reaction employing Nβ-protected-amino alkyl isonitrile, amino acid ester, aldehyde, and glycosyl acid has resulted in novel glycosylated peptidomimetics. The extension of MCR products for the synthesis of N,N′-orthogonally protected glycosylated peptidomimetics has also been demonstrated.

  采用的Ugi-4C反应Ñ β -保护的氨基烷基异腈，氨基酸酯，醛和糖基酸已导致新颖糖基化的肽模拟物。还已经证明了MCR产物用于合成N，N'-正交保护的糖基化肽模拟物的扩展。
• 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。
• Chiral Nβ-Fmoc-amino alkyl isonitriles in Ugi-4CR: an assembly of novel 1,1′-iminodicarboxylated peptidomimetics
  作者：N. Narendra、T.M. Vishwanatha、G. Nagendra、Vommina V. Sureshbabu

  DOI：10.1016/j.tet.2011.12.037

  日期：2012.2

  Enantiopure N-beta-Fmoc-amino alkyl isonitriles and amino acid esters have been employed as building blocks in Ugi four-component reaction (U-4CR) to yield 1,1 '-iminodicarboxylated peptidomimetics. By employing trifluoroacetic acid as one of the components, a different outcome has been observed and rationalized. Ugi products are obtained as trifluoroacetamide adducts, which on further reaction under mild acidic conditions lead to the title compounds. The method has also been proven to be useful for the preparation of ethyl, benzyl and tert-butyl esters. (C) 2011 Elsevier Ltd. All rights reserved.