(S)-1-azido-2-isocyano-3-methylbutane | 1223635-85-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-1-azido-2-isocyano-3-methylbutane
• 英文别名: (2S)-1-azido-2-isocyano-3-methylbutane
• CAS: 1223635-85-5
• 化学式: C₆H₁₀N₄
• 分子量: 138.172
• InChiKey: FECQVJGCCPOYBL-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-azido-2-isocyano-3-methylbutane 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 [1-((2S)-2-{[N-benzyl-N-(trifluoroacetyl)glycyl]amino}-3-methylbutyl)-1H-1,2,3-triazol-4-yl]methyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl methylphosphonate
  参考文献：
  名称：

  Synthesis and testing of trifluoromethyl-containing phosphonate–peptide conjugates as inhibitors of serine hydrolases

  摘要：

  A modification of novel fluorinated organophosphorous compounds containing terminal alkyne group by different azidopeptides via Cu(I)-catalyzed click chemistry has been described. The inhibitor activity of trifluoromethyl-containing methylphosphonates and their peptide-conjugates towards acetylcholinesterase, butyrylcholinesterase, and carboxylesterase has been investigated. It was shown that the incorporation of peptide fragments significantly modulates the esterase profile of starting methylphosphonates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.030
• 作为产物：
  描述：

  (2S)-2-isocyano-3-methylbutyl methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以60%的产率得到(S)-1-azido-2-isocyano-3-methylbutane
  参考文献：
  名称：

  手性异氰基叠氮化物：用于生物偶联的高效双功能试剂

  摘要：

  可以有效合成结合异氰化物和叠氮化物基团的手性支架，以允许有效构建氨基（羟基）酸和三唑衍生物，从而能够通过 Ugi/click 或 click/Ugi 策略制备杂化肽分子。

  DOI：

  10.1002/ejoc.200901326

文献信息

• Synthesis and biological activity of <i>N</i>-substituted-tetrahydro-γ-carbolines containing peptide residues
  作者：Nadezhda V Sokolova、Valentine G Nenajdenko、Vladimir B Sokolov、Daria V Vinogradova、Elena F Shevtsova、Ludmila G Dubova、Sergey O Bachurin

  DOI：10.3762/bjoc.10.13

  日期：——

  The synthesis of novel peptide conjugates of N-substituted-tetrahydro-gamma-carbolines has been performed using the sequence of the Ugi multicomponent reaction and Cu(I)-catalyzed click chemistry. The effect of obtained gamma-carboline-peptide conjugates on the rat liver mitochondria was evaluated. It was found that all compounds in the concentration of 30 microM did onot induce depolarization of mitochondria

  N-取代-四氢-γ-咔啉的新型肽缀合物的合成已使用 Ugi 多组分反应和 Cu (I) 催化点击化学的序列进行。评估了获得的γ-咔啉-肽缀合物对大鼠肝线粒体的影响。发现30μM浓度的所有化合物均不诱导线粒体去极化，但对线粒体通透性转变具有一定的抑制作用。含有末端炔基的原始 N-取代四氢-γ-咔啉表现出很高的促氧化活性，而它们与肽片段的结合物略微抑制了自氧化和 t-BHP 诱导的脂质过氧化。
• Synthesis of macrocyclic peptidomimetics <i>via</i> the Ugi-click-strategy
  作者：Elena A. Zakharova、Olga I. Shmatova、Irina V. Kutovaya、Victor N. Khrustalev、Valentine G. Nenajdenko

  DOI：10.1039/c9ob00229d

  日期：——

  Ugi-click-strategy was employed for the synthesis of 12–28 membered 1,2,3-triazole derived macrocyclic peptidomimetics. The Ugi reaction with acid components bearing acetylenic fragments and azidoisocyanides provided the corresponding peptidomimetics in up to 97% isolated yield. The subsequent CuAAC click reaction with these bifunctional substrates containing both acetylene and azide groups was investigated

  Ugi-click-strategy用于合成12-28元1,2,3-三唑衍生的大环拟肽。与带有乙炔片段和叠氮异氰酸酯的酸组分的Ugi反应以高达97％的分离产率提供了相应的拟肽。研究了与这些同时含有乙炔和叠氮基团的双功能底物的CuAAC点击反应，以揭示Ugi产品结构对点击环化方向的影响。结果表明，这种方法可以有效合成单体（12元和13元）或二聚体（24元，26元和28元）大环化合物，产率最高可达85％。讨论了该方法的范围和局限性。
• Synthesis of CF3-containing tetrapeptide surrogates via Ugi reaction/dipolar cycloaddition sequence
  作者：Daria V. Vorobyeva、Nadezhda V. Sokolova、Valentine G. Nenajdenko、Alexander S. Peregudov、Sergey N. Osipov

  DOI：10.1016/j.tet.2011.11.037

  日期：2012.1

  A convenient synthetic pathway to novel functionalized tetrapeptides containing the 1,2,3-triazole moiety is described. The target molecules were obtained by the reaction of fluorinated alpha-amino acids or alpha-aminophosphonates with azidopeptides via Cu(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). The synthesized tetrapeptides may find important applications in biomedical chemistry as potential drugs. (C) 2011 Elsevier Ltd. All rights reserved.
• Betulonic acid–peptide conjugates: synthesis and evaluation of anti-inflammatory activity
  作者：Anastasiya I. Govdi、Sergei F. Vasilevsky、Nadezhda V. Sokolova、Irina V. Sorokina、Tatyana G. Tolstikova、Valentine G. Nenajdenko

  DOI：10.1016/j.mencom.2013.09.007

  日期：2013.9

  Cycloaddition of betulonic acid propargyl ester and azido-containing Boc-protected peptides afforded the corresponding 1,2,3-triazole-linked conjugates, whose anti-inflammatory properties were studied.