(5S,14S)-5,14-diethoxycarbonyl-2,11-dioxa-4,13-diazapentacyclo[11.5.3.3.^4,16O.^10,23O.^1,20]tetracosa-1(18),7,9,16,20,23-hexaene | 1130299-92-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5S,14S)-5,14-diethoxycarbonyl-2,11-dioxa-4,13-diazapentacyclo[11.5.3.3.^4,16O.^10,23O.^1,20]tetracosa-1(18),7,9,16,20,23-hexaene
• 英文别名: diethyl (2S,11S)-8,17-dioxa-1,10-diazapentacyclo[11.5.3.34,10.016,20.07,23]tetracosa-4(24),5,7(23),13(21),14,16(20)-hexaene-2,11-dicarboxylate
• CAS: 1130299-92-1
• 化学式: C₂₆H₃₀N₂O₆
• 分子量: 466.534
• InChiKey: VLQSZHMQPPRMSK-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5S,14S)-5,14-diethoxycarbonyl-2,11-dioxa-4,13-diazapentacyclo[11.5.3.3.^4,16O.^10,23O.^1,20]tetracosa-1(18),7,9,16,20,23-hexaene 在 盐酸 作用下， 以 水 为溶剂， 以94%的产率得到(4S,13S)-9,18-dihydroxy-3,12-diazatricyclo[13.3.1.16,10]icosa-1(18),6(20),7,9,15(19),16-hexaene-4,13-dicarboxylic acid
  参考文献：
  名称：

  左旋酪氨酸氮杂环烷的合成与构象分析

  摘要：

  提出了由两个1-酪氨酸单元和两个亚甲基桥连接形成的新氮杂环烷的合成。简要讨论了结构和构象特征。光谱和理论数据揭示了具有两个分子内氢键的顺式结构。

  DOI：

  10.1016/j.tetlet.2009.12.116
• 作为产物：
  描述：

  聚合甲醛 、 L-酪氨酸乙酯 以 甲醇 为溶剂， 以63%的产率得到(5S,14S)-5,14-diethoxycarbonyl-2,11-dioxa-4,13-diazapentacyclo[11.5.3.3.^4,16O.^10,23O.^1,20]tetracosa-1(18),7,9,16,20,23-hexaene
  参考文献：
  名称：

  A structural study of the intermolecular interactions of tyramine in the solid state and in solution

  摘要：

  The nature of the interactions between tyramine units was investigated in the solid state and in solution. Crystals of tyramine in its free base form were analyzed by Fourier transform infrared (FT-IR) spectroscopy and single-crystal X-ray diffraction (XRD). The crystal structure shows a linear molecular organization held together by "head-to-tail" intermolecular hydrogen bonds between the amino groups and the phenolic hydroxyl groups. These chains are arranged in double layers that can geometrically favor the formation of templates in solution, which may facilitate macrocyclization reactions to form azacyclophane-type compounds. Computational calculations using the PM6-DH+ method and electrospray ionization mass spectrometry (ESI-HRMS) reveal that the formation of a hydrogen-bonded tyramine dimer is favored in solution. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.07.013

文献信息

• 1H- and 13C-NMR spectroscopic study of intermolecular interactions between tyrosine-derived azacyclophanes and aromatic rings
  作者：Rodolfo Quevedo

  DOI：10.1016/j.molstruc.2020.127777

  日期：2020.5

  Abstract This article analyses intermolecular interactions in solution between l -tyrosine-derived pentacyclic azacyclophanes and some aromatic compounds (p-tert-butylphenol, 2-tert-butyl-4-methoxyphenol and benzene). The results showed that these azacyclophanes formed complexes with aromatic compounds, in a 1:1 ratio, by means of pi-stacking.

  摘要 本文分析了l-酪氨酸衍生的五环氮杂环芳烃与一些芳香族化合物（对叔丁基苯酚、2-叔丁基-4-甲氧基苯酚和苯）在溶液中的分子间相互作用。结果表明，这些氮杂环芳烃通过π-堆积与芳香族化合物以1:1的比例形成复合物。
• Synthesis of macrocyclic α-amino esters through the chemoselective hydrolysis of benzoxazinephanes
  作者：Rodolfo Quevedo、Marlon González、Christian Díaz-Oviedo

  DOI：10.1016/j.tetlet.2012.01.064

  日期：2012.3

  New meso-macrocyclic a-amino esters were synthesized through the chemoselective hydrolysis of azacyclophanes derived from L.-tyrosine (benzoxazinephanes). The results showed that the alkyl chain of the ester determined the chemoselectivity of the reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• One-step synthesis of a new heterocyclophane family
  作者：Rodolfo Quevedo、Bárbara Moreno-Murillo

  DOI：10.1016/j.tetlet.2008.12.023

  日期：2009.2

  New macrocyclic compounds having two benzoxazine subunits joined by two ethylene bridges have been prepared by Mannich condensation of the appropriate 4-hydi-oxyphenylethylamine with an excess of formaldehyde. This is a general method for synthesising a new family of heterocyclophanes. (C) 2008 Elsevier Ltd. All rights reserved.
• Intrinsic Fluorescence of 1,3-Benzoxazinephanes
  作者：Rodolfo Quevedo、Cesar A. Sierra

  DOI：10.3987/com-11-12324

  日期：——

  A new 1,3-benzoxazine nuclei-based fluorescent system is presented. The photophysical aspects are briefly discussed. The results suggested that the presence of oxazinic methylenes is necessary for fluorescence to be present.
• A structural study of the intermolecular interactions of tyramine in the solid state and in solution
  作者：Rodolfo Quevedo、Nelson Nuñez-Dallos、Klaus Wurst、Álvaro Duarte-Ruiz

  DOI：10.1016/j.molstruc.2012.07.013

  日期：2012.12

  The nature of the interactions between tyramine units was investigated in the solid state and in solution. Crystals of tyramine in its free base form were analyzed by Fourier transform infrared (FT-IR) spectroscopy and single-crystal X-ray diffraction (XRD). The crystal structure shows a linear molecular organization held together by "head-to-tail" intermolecular hydrogen bonds between the amino groups and the phenolic hydroxyl groups. These chains are arranged in double layers that can geometrically favor the formation of templates in solution, which may facilitate macrocyclization reactions to form azacyclophane-type compounds. Computational calculations using the PM6-DH+ method and electrospray ionization mass spectrometry (ESI-HRMS) reveal that the formation of a hydrogen-bonded tyramine dimer is favored in solution. (C) 2012 Elsevier B.V. All rights reserved.