benzyl N-[(5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-6-isocyanohexyl]carbamate | 1095038-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: benzyl N-[(5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-6-isocyanohexyl]carbamate
• CAS: 1095038-08-6
• 化学式: C₃₀H₃₁N₃O₄
• 分子量: 497.594
• InChiKey: WVRGYQVGXGHCQH-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-[(5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-6-isocyanohexyl]carbamate 、 苯甲醛 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.33h， 生成 (2S)-methyl 2-(2-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-6-(benzyloxycarbonyl)hexylamino)-2-oxo-1-phenylethylamino)propanoate
  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：

  在 4-二甲氨基吡啶 、 甲酸 、 伯吉斯试剂 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl N-[(5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-6-isocyanohexyl]carbamate
  参考文献：
  名称：

  Synthesis of β-lactam peptidomimetics through Ugi MCR: first application of chiral Nβ-Fmoc amino alkyl isonitriles in MCRs

  摘要：

  Chiral N-beta-Fmoc amino alkyl isonitriles were employed in Ugi multi component reactions (Ugi 4C-3CR) to obtain functionalized beta-lactam peptidomimetics with L-aspartic acid alpha-methyl ester/peptide ester and organic aldehydes. The reactions were carried out in MeOH. Thirteen Ugi products have been prepared in good to moderate yields with good diastereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.090