((1R,2S)-1-Isocyanato-2-methyl-butyl)-carbamic acid 9H-fluoren-9-ylmethyl ester | 611198-22-2

• 分子结构分类: 有机化合物
• 英文名称: ((1R,2S)-1-Isocyanato-2-methyl-butyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS: 611198-22-2
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: ZJBGAXXMFUBDFL-XOBRGWDASA-N

物化性质

• 熔点：
  104 °C
• 沸点：
  506.5±33.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((1R,2S)-1-Isocyanato-2-methyl-butyl)-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 为溶剂， 以80%的产率得到(9H-fluoren-9-yl)methyl (1S,2S)-1-formamido-2-methylbutylcarbamate
  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：

  Fmoc-Ile-N₃ 以 甲苯 为溶剂， 反应 0.5h， 生成 ((1R,2S)-1-Isocyanato-2-methyl-butyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Synthesis of N ^α -Protected Amino Acid–Derived Selenocarbamates Employing Isocyanates as Key Intermediates

  摘要：

  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.

  DOI：

  10.1080/00397910903318641

文献信息

• Synthesis of retro-inverso peptides employing isocyanates of Nα-Fmoc-amino acids/peptide acids catalyzed by DMAP
  作者：Rao Venkataramanarao、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2006.10.066

  日期：2006.12

  The Goldschmidt-Wick type reaction between isocyanates of N-alpha-Fmoc-amino acids/peptide acids and N-alpha-Boc-/Z-/ Bsmoc-amino acids catalyzed by DMAP leads to the incorporation of a reversed peptide bond. It was found to be a simple, efficient and clean reaction. All the retro-inverso peptides made were obtained as crystalline compounds in 70-92% yields. (c) 2006 Elsevier Ltd. All rights reserved.
• 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：——
• Patil, Basanagoud S.; Suresh Babu, Vommina V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 8, p. 1721 - 1728
  作者：Patil, Basanagoud S.、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.