tert-butyl N-[6-(benzylamino)hexyl]carbamate | 174799-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-[6-(benzylamino)hexyl]carbamate
• CAS: 174799-53-2
• 化学式: C₁₈H₃₀N₂O₂
• 分子量: 306.448
• InChiKey: GQFLYXQETKSHHX-UHFFFAOYSA-N

物化性质

• 沸点：
  433.4±28.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[6-(benzylamino)hexyl]carbamate 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 50.5h， 生成 (2S)-2-[9H-fluoren-9-ylmethoxycarbonyl-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]amino]propanoic acid
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e
• 作为产物：
  描述：

  1,6-己二胺 在 sodium tetrahydroborate 、 magnesium sulfate 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 20.5h， 生成 tert-butyl N-[6-(benzylamino)hexyl]carbamate
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e

文献信息

• Synthesis of Bivalent β₂-Adrenergic and Adenosine A₁ Receptor Ligands
  作者：Peter Karellas、Michael McNaughton、Stephen P. Baker、Peter J. Scammells

  DOI：10.1021/jm800613s

  日期：2008.10.9

  Research in the area of simutaneously targeting more than one G protein-coupled receptor (GPCR) has increased in recent times. By exploiting the cross talk between the beta(2)-adrenergic (beta(2)AR) and adenosine A(1) receptors (A(1)AR) on adenylate cyclase activity, we synthesized a series of bivalent agonists for both GPCRs to generate responses from more than one receptor. We have demonstrated a relationship between the various beta(2)-adrenergic and A(1) adenosine bivalent parameters of linker and bifunctionality by using data that are drawn from in vitro assays. The hexyl-linked 12e (K-i, 311 nM) and butyl-linked 12c (K-i, 863 nM) bivalent compounds displayed reasonable binding affinities for the PAR when compared with the control (-)isoproterenol (K-i, 136 nM), and both compounds also exhibited a persuasive bifunctional trend for both receptors at various drug concentrations. The bivalent compound 12e was also found to have significant EC50 potency (6 nM) at the beta(2)AR in DDT cells.