(9H-fluoren-9-yl)methyl 2-((2-(N-(1-(benzyloxy)-3-methyl-1-oxobutan-2-yl)-2,2,2-trifluoroacetamido)acetamido)methyl)pyrrolidine-1-carboxylate | 1359084-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl 2-((2-(N-(1-(benzyloxy)-3-methyl-1-oxobutan-2-yl)-2,2,2-trifluoroacetamido)acetamido)methyl)pyrrolidine-1-carboxylate
• CAS: 1359084-97-1
• 化学式: C₃₆H₃₈F₃N₃O₆
• 分子量: 665.709
• InChiKey: ARDUDSBPTQZIMC-UKJJDJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  48.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  105.25
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl 2-((2-(N-(1-(benzyloxy)-3-methyl-1-oxobutan-2-yl)-2,2,2-trifluoroacetamido)acetamido)methyl)pyrrolidine-1-carboxylate 在 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到(S)-(9H-fluoren-9-yl)methyl 2-((2-((S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-ylamino)acetamido)methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Chiral Nβ-Fmoc-amino alkyl isonitriles in Ugi-4CR: an assembly of novel 1,1′-iminodicarboxylated peptidomimetics

  摘要：

  Enantiopure N-beta-Fmoc-amino alkyl isonitriles and amino acid esters have been employed as building blocks in Ugi four-component reaction (U-4CR) to yield 1,1 '-iminodicarboxylated peptidomimetics. By employing trifluoroacetic acid as one of the components, a different outcome has been observed and rationalized. Ugi products are obtained as trifluoroacetamide adducts, which on further reaction under mild acidic conditions lead to the title compounds. The method has also been proven to be useful for the preparation of ethyl, benzyl and tert-butyl esters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.037
• 作为产物：
  描述：

  聚合甲醛 、 L-亮氨酸 、 (9H-fluoren-9-yl)methyl (S)-2-(isocyanomethyl)pyrrolidine-1-carboxylate 、 三氟乙酸 、 苯甲醇 反应 2.33h， 以79%的产率得到(9H-fluoren-9-yl)methyl 2-((2-(N-(1-(benzyloxy)-3-methyl-1-oxobutan-2-yl)-2,2,2-trifluoroacetamido)acetamido)methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Chiral Nβ-Fmoc-amino alkyl isonitriles in Ugi-4CR: an assembly of novel 1,1′-iminodicarboxylated peptidomimetics

  摘要：

  Enantiopure N-beta-Fmoc-amino alkyl isonitriles and amino acid esters have been employed as building blocks in Ugi four-component reaction (U-4CR) to yield 1,1 '-iminodicarboxylated peptidomimetics. By employing trifluoroacetic acid as one of the components, a different outcome has been observed and rationalized. Ugi products are obtained as trifluoroacetamide adducts, which on further reaction under mild acidic conditions lead to the title compounds. The method has also been proven to be useful for the preparation of ethyl, benzyl and tert-butyl esters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.037