((S)-2-Azidocarbonyl-1-methyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester | 270575-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ((S)-2-Azidocarbonyl-1-methyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS: 270575-65-0
• 化学式: C₁₉H₁₈N₄O₃
• 分子量: 350.377
• InChiKey: ZUENHOODVQUUOE-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  104.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((S)-2-Azidocarbonyl-1-methyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 在 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-formamidopropan-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
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 ((S)-2-Azidocarbonyl-1-methyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  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

文献信息

• 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。
• Solid phase synthesis of oligoureas using O-succinimidyl-(9H-fluoren-9-ylmethoxycarbonylamino)ethylcarbamate derivatives as activated monomers
  作者：Gilles Guichard、Vincent Semetey、Marc Rodriguez、Jean-Paul Briand

  DOI：10.1016/s0040-4039(99)02353-9

  日期：2000.3

  An efficient stepwise synthesis of oligoureas (up to the nonamer) on solid support using O-succinimidyl-(9H-fluoren-9-ylmethoxycarbonylamino)ethylcarbamate derivatives as activated monomers is described. These building blocks were readily prepared starting from N-Fmoc-protected β3-amino acids via Curtius rearrangement of the corresponding acyl azides and treatment of the resulting isocyanate with

  描述了使用O-琥珀酰亚胺基- （9 H-芴-9-基甲氧基羰基氨基）乙基氨基甲酸酯衍生物作为活化单体在固相载体上高效逐步合成寡聚脲（直至九聚体）的方法。这些构建块被容易地制备，起始自Ñ -Fmoc保护的β 3 -氨基酸经由相应的酰基叠氮化物和治疗与所得的异氰酸酯的Curtius重排Ñ羟基琥珀酰亚胺。
• Helix-Forming Oligoureas: Temperature-Dependent NMR, Structure Determination, and Circular Dichroism of a Nonamer with Functionalized Side Chains
  作者：Christine Hemmerlin、Michel Marraud、Didier Rognan、Roland Graff、Vincent Semetey、Jean-Paul Briand、Gilles Guichard

  DOI：10.1002/1522-2675(200211)85:11<3692::aid-hlca3692>3.0.co;2-w

  日期：2002.11

  To further investigate the degree of structural homology between gamma-peptides A and NX-Iinked oligoureas B, we prepared oligourea nonamer 2 containing Ala, Val, Leu, Phe, Tyr and Lys side chains. Oligomer 2 was synthesized on solid support from activated monomers, i.e., from enantiomerically pure succinimidyl (2-[(9H-fluoren-9-ylmethoxy)carbonyl]amino) ethyl)carbamates 3a-f that are further substituted at C(2) of the ethyl moiety. These precursors were conveniently prepared from N-Fmoc-protected beta(3)-amino acids with corresponding side chains. Detailed NMR studies (DQF-COSY, TOCSY, and ROESY) in (D-5)pyridine revealed that 2 adopts a regular (P)-2.5 helical secondary structure very similar to that previously determined for oligourea heptamer 1 and closely related to the (P)-2.6(14) helix of gamma-peptides. Temperature-dependent NMR further demonstrated the conformational homogeneity and remarkable stability of the structure of 2 in pyridine. The CD spectrum of 2 (0.2 mm) was recorded in MeOH with the aim to gain more information about the conformation of oligoureas. In contrast to 2.6-helical gamma-peptides, which display only a weak or no Cotton effect, oligourea 2 exhibits an intense positive Cotton effect at ca. 203 nm ([Theta] = + 373000 deg cm(2) dmol(-1)) that decreases only slowly upon increasing the temperature.