14-(2-tert-butoxycarbonylaminoethyl)-6,7,9,10,13,14,15,16,18,19,21,22-dodecahydro-12H-5,8,11,17,20,23-hexaoxa-14-aza-benzocycloheneicosene-2,3-dicarboxylic acid dimethyl ester | 841260-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 14-(2-tert-butoxycarbonylaminoethyl)-6,7,9,10,13,14,15,16,18,19,21,22-dodecahydro-12H-5,8,11,17,20,23-hexaoxa-14-aza-benzocycloheneicosene-2,3-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 11-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-2,5,8,14,17,20-hexaoxa-11-azabicyclo[19.4.0]pentacosa-1(21),22,24-triene-23,24-dicarboxylate
• CAS: 841260-34-2
• 化学式: C₂₉H₄₆N₂O₁₂
• 分子量: 614.69
• InChiKey: QTYOPBDMPOARKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  14-(2-tert-butoxycarbonylaminoethyl)-6,7,9,10,13,14,15,16,18,19,21,22-dodecahydro-12H-5,8,11,17,20,23-hexaoxa-14-aza-benzocycloheneicosene-2,3-dicarboxylic acid dimethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以100%的产率得到dilithium 14-(2-tert-butoxycarbonylaminoethyl)-6,7,9,10,13,14,15,16,18,19,21,22-dodecahydro-12H-5,8,11,17,20,23-hexaoxa-14-aza-benzocycloheneicosene-2,3-dicarboxylate
  参考文献：
  名称：

  Luminescent Crown Ether Amino Acids:  Selective Binding to N-terminal Lysine in Peptides

  摘要：

  Crown ether amino acids (CEAAs) with a luminescent phthalic ester or phthalimide moiety have been prepared. Simple peptide chemistry covalently tethers the macrocycles to give ditopic ammonium-ion binders. The binding events of both crown ether groups are monitored independently by changes of their specific emission properties. The affinity of the bis-CEAA to bis-ammonium ions is distance dependent, which allows distinguishing between isomeric small peptides containing a lysine residue in different positions.

  DOI：

  10.1021/jo048105y
• 作为产物：
  描述：

  4,5-bis{2-[2-2-(2-hydroxyethoxy)ethoxy]ethoxy}phthalic acid dimethyl ester 在 氢氧化钾 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 14-(2-tert-butoxycarbonylaminoethyl)-6,7,9,10,13,14,15,16,18,19,21,22-dodecahydro-12H-5,8,11,17,20,23-hexaoxa-14-aza-benzocycloheneicosene-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Luminescent Crown Ether Amino Acids:  Selective Binding to N-terminal Lysine in Peptides

  摘要：

  Crown ether amino acids (CEAAs) with a luminescent phthalic ester or phthalimide moiety have been prepared. Simple peptide chemistry covalently tethers the macrocycles to give ditopic ammonium-ion binders. The binding events of both crown ether groups are monitored independently by changes of their specific emission properties. The affinity of the bis-CEAA to bis-ammonium ions is distance dependent, which allows distinguishing between isomeric small peptides containing a lysine residue in different positions.

  DOI：

  10.1021/jo048105y

文献信息

• Modular synthesis of di- and tripeptides of luminescent crown ether aminocarboxylic acids
  作者：Andreas Späth、Burkhard König

  DOI：10.1016/j.tet.2008.10.086

  日期：2009.1

  Luminescent benzo crown ether aminocarboxylic acids with ammonium ion affinity were prepared and converted into linear bis- and tris benzo crown ether amides using standard peptide coupling protocols. The affinities of the new crown ethers to ammonium ions and di- and tetrapeptides bearing ammonium ion moieties were determined by emission titration in methanol and buffered water.

  制备具有铵离子亲和力的发光苯并冠醚氨基羧酸，并使用标准的肽偶联方案将其转化为线性的双和三苯并冠醚酰胺。通过在甲醇和缓冲水中的发射滴定确定新的冠醚对铵离子以及带有铵离子部分的二肽和四肽的亲和力。
• Luminescent Crown Ether Amino Acids:  Selective Binding to <i>N</i>-terminal Lysine in Peptides
  作者：Christian P. Mandl、Burkhard König

  DOI：10.1021/jo048105y

  日期：2005.1.1

  Crown ether amino acids (CEAAs) with a luminescent phthalic ester or phthalimide moiety have been prepared. Simple peptide chemistry covalently tethers the macrocycles to give ditopic ammonium-ion binders. The binding events of both crown ether groups are monitored independently by changes of their specific emission properties. The affinity of the bis-CEAA to bis-ammonium ions is distance dependent, which allows distinguishing between isomeric small peptides containing a lysine residue in different positions.