9H-fluoren-9-ylmethyl N-[(S)-isocyanato(phenyl)methyl]carbamate | 611198-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-[(S)-isocyanato(phenyl)methyl]carbamate
• CAS: 611198-68-6
• 化学式: C₂₃H₁₈N₂O₃
• 分子量: 370.408
• InChiKey: BJQPHLXHKWEZLF-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  9H-fluoren-9-ylmethyl N-[(S)-isocyanato(phenyl)methyl]carbamate 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.75h， 生成 methyl (2S)-2-[[(R)-(9H-fluoren-9-ylmethoxycarbonylamino)-phenylmethyl]carbamoylamino]-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis of Peptidyl Ureas Using p‐Nitrophenyl‐(9‐fluorenylmethoxy Carbonylamino)methyl Carbamate Derivatives

  摘要：

  An efficient synthesis of p-nitrophenyl-(9-fluorenylmethoxy, carbonylamino) methyl carbamates using isocyanates derived from Fmoc-amino acid azides and p-nitrophenol in presence of an equimolar quantity of N-ethyldiisopropyl amine is described. All the carbamates have been isolated as crystalline solids and are fully characterized. Further, their utility for the synthesis of dipeptidyl ureas has been demonstrated.

  DOI：

  10.1081/scc-120039483
• 作为产物：
  描述：

  Fmoc-(D)Phg-N3 以 甲苯 为溶剂， 反应 0.33h， 生成 9H-fluoren-9-ylmethyl N-[(S)-isocyanato(phenyl)methyl]carbamate
  参考文献：
  名称：

  Synthesis of Peptidyl Ureas Using p‐Nitrophenyl‐(9‐fluorenylmethoxy Carbonylamino)methyl Carbamate Derivatives

  摘要：

  An efficient synthesis of p-nitrophenyl-(9-fluorenylmethoxy, carbonylamino) methyl carbamates using isocyanates derived from Fmoc-amino acid azides and p-nitrophenol in presence of an equimolar quantity of N-ethyldiisopropyl amine is described. All the carbamates have been isolated as crystalline solids and are fully characterized. Further, their utility for the synthesis of dipeptidyl ureas has been demonstrated.

  DOI：

  10.1081/scc-120039483

文献信息

• An Efficient Conversion of the Carboxylic Group of <i>N</i>-Fmoc α-Amino Acids/Peptide Acids into <i>N</i>-Formamides Employing Isocyanates as Key Intermediates
  作者：N. S. Sudarshan、N. Narendra、H. P. Hemantha、Vommina V. Sureshbabu

  DOI：10.1021/jo701371k

  日期：2007.12.1

  [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.
• Patil, Basanagoud S.; Vasanthakumar, Ganga-Ramu; Suresh Babu, Vommina V., Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7274 - 7280
  作者：Patil, Basanagoud S.、Vasanthakumar, Ganga-Ramu、Suresh Babu, Vommina V.

  DOI：——

  日期：——
• Suresh Babu, Vommina V.; Kantharaju, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 5, p. 1046 - 1053
  作者：Suresh Babu, Vommina V.、Kantharaju

  DOI：——

  日期：——
• Synthesis of Peptidyl Ureas Using <i>p</i>‐Nitrophenyl‐(9‐fluorenylmethoxy Carbonylamino)methyl Carbamate Derivatives
  作者：Basanagoud S. Patil、Ganga‐Ramu Vasanthakumar、Vommina V. Suresh Babu

  DOI：10.1081/scc-120039483

  日期：2004.1.1

  An efficient synthesis of p-nitrophenyl-(9-fluorenylmethoxy, carbonylamino) methyl carbamates using isocyanates derived from Fmoc-amino acid azides and p-nitrophenol in presence of an equimolar quantity of N-ethyldiisopropyl amine is described. All the carbamates have been isolated as crystalline solids and are fully characterized. Further, their utility for the synthesis of dipeptidyl ureas has been demonstrated.