Fmoc-Phe-NCO | 611198-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Phe-NCO
• 英文别名: 9H-fluoren-9-ylmethyl N-[(1R)-1-isocyanato-2-phenylethyl]carbamate
• CAS: 611198-23-3
• 化学式: C₂₄H₂₀N₂O₃
• 分子量: 384.434
• InChiKey: QHJJJHHEWODDJM-QHCPKHFHSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  578.7±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Fmoc-Phe-NCO 在 4-二甲氨基吡啶 、 甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以89%的产率得到(S)-(9H-fluoren-9-yl)methyl 1-formamido-2-phenylethylcarbamate
  参考文献：
  名称：

  An Efficient Conversion of the Carboxylic Group of N-Fmoc α-Amino Acids/Peptide Acids into N-Formamides Employing Isocyanates as Key Intermediates

  摘要：

  [Graphics]Reaction of 96% formic acid with isocyanates derived from N-Fmoc alpha-amino acids/peptide acids catalyzed by DMAP has yielded a new class of stable formamides as crystalline solids which have been characterized by IR, H-1 NMR, C-13 NMR, and mass spectroscopy. Conversion of the side chain carboxylic acid of N-Fmoc-5-oxazolidinones of Asp/Glu into the N-formyl group also has been accomplished. The reaction is simple, mild, and high yielding.

  DOI：

  10.1021/jo701371k
• 作为产物：
  描述：

  N-[(1S)-2-氯-2-氧代-1-(苯甲基)乙基]-氨基甲酸-9H-芴-9-甲酯 在 sodium azide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 1.25h， 生成 Fmoc-Phe-NCO
  参考文献：
  名称：

  Babu, Vommina V. Suresh; Ananda, Kuppanna; Vasanthakumar, Ganga-Ramu, Journal of the Chemical Society. Perkin transactions I, 2000, # 24, p. 4328 - 4331

  摘要：

  DOI：

文献信息

• 1-Propanephosphonic Acid Cyclic Anhydride (T3P) as an Efficient Promoter for the Lossen Rearrangement: Application to the Synthesis of Urea and Carbamate Derivatives
  作者：Vommina Sureshbabu、Basavalingappa Vasantha、Hosahalli Hemantha

  DOI：10.1055/s-0030-1258158

  日期：2010.9

  The synthesis of hydroxamic acids starting from carboxylic acids employing 1-propanephosphonic acid cyclic anhydride (T3P) activation is described. Application of ultrasonication accelerates this conversion. Further, the T3P has also been employed to activate the hydroxamates, leading to isocyanates via the Lossen rearrangement. The isocyanates were trapped with suitable nucleophiles to afford the

  描述了使用1-丙烷膦酸环酐（T3P）活化从羧酸开始的异羟肟酸的合成。超声处理的应用加速了这种转化。此外，T3P也已用于活化异羟肟酸酯，通过Lossen重排产生异氰酸酯。用合适的亲核试剂捕获异氰酸酯，得到相应的脲和氨基甲酸酯。 T3P-异羟肟酸-洛森重排-异氰酸酯
• New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: application of peptide coupling agents EDC and HBTU
  作者：Vommina V. Sureshbabu、H. S. Lalithamba、N. Narendra、H. P. Hemantha

  DOI：10.1039/b920290k

  日期：——

  Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved.

  使用肽偶联剂，EDC和 HBTU描述。该程序高效，实用并且适用于多种羧酸，包括ñ保护的氨基酸。使用相同的试剂，还可以从酸一锅合成尿素，二肽基脲酯和氨基甲酸酯。
• A Facile Synthesis of Hydroxamic Acids of<i>N^α</i>-Protected Amino Acids Employing BDMS, a Study of Their Molecular Docking and Their Antibacterial Activities
  作者：K. Uma、H. S. Lalithamba、V. Chandramohan、K. Lingaraju

  DOI：10.1080/00304948.2019.1579039

  日期：2019.3.4

  Hydroxamic acids have received much attention as biologically active compounds. Synthetic hydroxamic acids enhance the growth of plant sources and improve the soil quality, act as antibiotics, cell...

  异羟肟酸作为生物活性化合物受到了很多关注。合成异羟肟酸可促进植物来源的生长并改善土壤质量，作为抗生素、细胞...
• Characterization of Nα-Fmoc-protected ureidopeptides by electrospray ionization tandem mass spectrometry (ESI-MS/MS): differentiation of positional isomers
  作者：M. Ramesh、B. Raju、R. Srinivas、V. V. Sureshbabu、N. Narendra、B. Vasantha

  DOI：10.1002/jms.1862

  日期：2010.12

  (9H‐fluoren‐9‐yl)methyl cation (C14H11+) from FmocNH = CHR+. In addition, characteristic immonium ions are also observed. The deprotonated ureidopeptide acids dissociate differently from the protonated ureidopeptides. The [M − H]− ions of ureidopeptide acids undergo a McLafferty‐type rearrangement followed by the loss of CO2 to form an abundant [M − H − Fmoc + H]− which is absent for protonated ureidopeptides

  四对脲肽位置异构体，FmocNH-CH（R 1）-φ（NH-CO-NH）-CH（R 2）-OY和FmocNH-CH（R 2）-φ（NH-CO-NH）- CH（R 1）-OY（Fmoc = [（9-芴基甲基）氧基]羰基; R 1 = H，烷基; R 2 =烷基，H和Y = CH 3 / H），已通过两种方法进行了表征和区分正离子和负离子电喷雾电离（ESI）离子阱串联质谱（MS / MS）。在MS注意到主要分段/所有这些化合物的MS是由于 Ñ  CH（R） Ñ 键裂解形成特征性的N和C端碎片离子。N端的甘氨酸衍生的质子化的尿苷肽酸在m / z 240时形成质子化的（9H-芴-9-9）甲基氨基甲酸酯离子，而相应的酯则不存在。在N端衍生自甘氨酸的尿苷肽中发现的另一个有趣的片段化是中间片段离子FmocNH = CH 2 +（m / z 252）导致的61个单位的异常丢失。一种涉及离子中性络合物以及NH
• Synthesis of <i>N</i> ^{<font>α</font>}-Protected Amino Acid–Derived Selenocarbamates Employing Isocyanates as Key Intermediates
  作者：Vommina V. Sureshbabu、Shankar A. Naik

  DOI：10.1080/00397910903318641

  日期：2010.8.16

  A simple protocol for the synthesis of N-urethane-protected N-alkyl-Se-alkyl selenocarbamate derivatives of amino acids has been described. The reaction of N-urethane-protected amino alkyl isocyanates with selenating agent LiAlHSeH and subsequent coupling with an alkyl halide yielded the title compounds in good yield and purity. All the selenocarbamates obtained have been characterized by 1H NMR, 13C NMR, and mass spectral studies.