(9H-fluoren-9-yl)methyl 2-formamidoethyl carbamate | 754976-81-3

• 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-formamidoethyl carbamate
• 英文别名: Fmoc-Gly-Ψ[CH2-NHCHO]；N-Fmoc-ethylamine-formamide
• CAS: 754976-81-3
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: AQMHYIFGYYOCRK-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C(Solv: dimethyl sulfoxide (67-68-5); water (7732-18-5))
• 沸点：
  587.4±33.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl 2-formamidoethyl carbamate 在 tetraphosphorus decasulfide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 9H-fluoren-9-ylmethyl N-[2-(methanethioylamino)ethyl]carbamate
  参考文献：
  名称：

  溴化氰作为脱氢硫化剂，用于从 Nβ-Fmoc-氨基烷基硫代甲酰胺合成 Nβ-Fmoc-氨基烷基异腈

  摘要：

  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。

  DOI：

  10.1055/s-0029-1219583
• 作为产物：
  描述：

  FMOC-beta-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 2-formamidoethyl carbamate
  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 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。
• Synthesis and structural characterization of monomeric and dimeric peptide nucleic acids prepared by using microwave-promoted multicomponent reactions
  作者：Reuben Ovadia、Aurélien Lebrun、Ivan Barvik、Jean-Jacques Vasseur、Carine Baraguey、Karine Alvarez

  DOI：10.1039/c5ob01604e

  日期：——

  A solution phase synthesis of peptide nucleic acid monomers and dimers was developed by using microwave-promoted Ugi multicomponent reactions.

  通过使用微波促进的Ugi多组分反应，开发了肽核酸单体和二聚体的溶液相合成方法。
• 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。
• Facile access to modified and functionalized PNAs through Ugi-based solid phase oligomerization
  作者：Jacques Saarbach、Daniela Masi、Claudio Zambaldo、Nicolas Winssinger

  DOI：10.1016/j.bmc.2017.05.064

  日期：2017.10

  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.