(9H-fluoren-9-yl)methyl (2-isocyanoethyl)carbamate | 663173-20-4

• 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 (2-isocyanoethyl)carbamate
• 英文别名: Fmoc-Gly-Ψ[CH2-NC]；9H-fluoren-9-ylmethyl N-(2-isocyanoethyl)carbamate
• CAS: 663173-20-4
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: ZIKYNZPAICESRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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 (2-isocyanoethyl)carbamate 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.58h， 生成
  参考文献：
  名称：

  Facile access to modified and functionalized PNAs through Ugi-based solid phase oligomerization

  摘要：

  Peptide nucleic acids (PNAs) derivatized with functional molecules are increasingly used in diverse biosupramolecular applications. PNAs have proven to be highly tolerant to modifications and different applications benefit from the use of modified PNAs, in particular modifications at the gamma position. Herein we report simple protocols to access modified PNAs from iterative Ugi couplings which allow modular modifications at the alpha, beta or gamma position of the PNA backbone from simple starting materials. We demonstrate the utility of the method with the synthesis of several bioactive small molecules (a peptide ligand, a kinase inhibitor and a glycan)-PNA conjugates. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.05.064
• 作为产物：
  描述：

  N-Fmoc-ethylenediamine 在 乙酸酐 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 (9H-fluoren-9-yl)methyl (2-isocyanoethyl)carbamate
  参考文献：
  名称：

  Facile access to modified and functionalized PNAs through Ugi-based solid phase oligomerization

  摘要：

  Peptide nucleic acids (PNAs) derivatized with functional molecules are increasingly used in diverse biosupramolecular applications. PNAs have proven to be highly tolerant to modifications and different applications benefit from the use of modified PNAs, in particular modifications at the gamma position. Herein we report simple protocols to access modified PNAs from iterative Ugi couplings which allow modular modifications at the alpha, beta or gamma position of the PNA backbone from simple starting materials. We demonstrate the utility of the method with the synthesis of several bioactive small molecules (a peptide ligand, a kinase inhibitor and a glycan)-PNA conjugates. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.05.064

文献信息

• Synthesis of Isonitriles from N-Substituted Formamides Using Triphenylphosphine and Iodine
  作者：Qun-Li Luo、Xia Wang、Qing-Gang Wang

  DOI：10.1055/s-0034-1379111

  日期：——

  alkyl and aryl isocyanides. Treatment of N-substituted formamides with the reagent combination of triphenylphosphine and molecular iodine, in the presence of a tertiary amine, quickly produces the corresponding isocyanides in high yields under ambient conditions. The process employs readily available and low-cost reagents, a convenient synthetic procedure, and mild reaction conditions for the synthesis

  摘要 在叔胺的存在下，用三苯基膦和分子碘的试剂组合处理N-取代的甲酰胺，可在环境条件下快速高产率地生产相应的异氰化物。该方法采用容易获得和低成本的试剂，方便的合成方法和温和的反应条件来合成各种烷基和芳基异氰酸酯。 在叔胺的存在下，用三苯基膦和分子碘的试剂组合处理N-取代的甲酰胺，可在环境条件下快速高产率地生产相应的异氰化物。该方法采用容易获得和低成本的试剂，方便的合成方法和温和的反应条件来合成各种烷基和芳基异氰酸酯。
• 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.
• 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.