endo-(S)-2-(3,5-dioxo-4-azatricyclo[5.2.1.0^2,6]dec-8-en-4-yl)-3-phenylpropionic acid

• 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: endo-(S)-2-(3,5-dioxo-4-azatricyclo[5.2.1.0^2,6]dec-8-en-4-yl)-3-phenylpropionic acid
• 英文别名: 2-(3,5-dioxo-4-azatricyclo[5.2.1.0^2,6]dec-8-en-4-yl)-3-phenylpropanoic acid；(2S)-2-[(1S,2R,6S,7R)-3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl]-3-phenylpropanoic acid
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: SBWQMIAVJWVRKE-AIEDFZFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  endo-(S)-2-(3,5-dioxo-4-azatricyclo[5.2.1.0^2,6]dec-8-en-4-yl)-3-phenylpropionic acid 生成 2-(4-azabicyclo[2.2.1]hept-8-ene-3-endo,5-endodicarboximide-4-yl)-3-phenyl propionyl chloride
  参考文献：
  名称：

  带有酰亚胺和脂环族片段的羧酸酰胺的合成及其在葱属试验中的遗传毒性研究

  摘要：

  已经开发了一种高产率合成几种含有酰亚胺、环己烯和降冰片烯环以及天然氨基酸片段的羧酸酰胺的方法。合成的化合物已使用葱属试验测试了对植物对象的诱变活性。已经表明，硝基的存在赋予化合物抑制特性和诱导染色体重排的能力，而脂肪族碳链、甲基和吗啉片段的存在相反，赋予生长-调节特性而不引起诱变效应。该研究已经证实，由此产生的生物活性化合物对于在农业中的实际应用具有重要意义。

  DOI：

  10.1134/s1068162019030026
• 作为产物：
  描述：

  L-苯基丙氨酸叔丁酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 endo-(S)-2-(3,5-dioxo-4-azatricyclo[5.2.1.0^2,6]dec-8-en-4-yl)-3-phenylpropionic acid
  参考文献：
  名称：

  General Synthesis of Unsymmetrical Norbornane Scaffolds as Inducers for Hydrogen Bond Interactions in Peptides^,

  摘要：

  Starting from readily accessible endo-cis-(2S,3R)-norbornene dicarboxylic acid benzyl monoester, a general and efficient synthetic approach toward unsymmetrical two-stranded peptidic structures was developed. In these structures the peptide strands are oriented in a parallel geometry. Their synthesis is easily applicable to a variety of amino acids and peptides. Specifically, a norbornane template as molecular scaffold induces hydrogen bonding between the adjacent peptide strands. The specific hydrogen bonding patterns between these strands were revealed by detailed NMR analysis including TOCSY/NOE experiments.

  DOI：

  10.1021/jo030295+

文献信息

• Synthesis of Amides of Carboxylic Acids with an Imide and Alicyclic Fragments and a Study of Their Genotoxic Activity in the Allium Test
  作者：A. A. Firstova、E. R. Kofanov、V. M. Zakshevskaya、M. I. Kovaleva

  DOI：10.1134/s1068162019030026

  日期：2019.5

  A method for the high-yield synthesis of several amides of carboxylic acids containing an imide, a cyclohexene, and a norbornene cycle as well as fragments of natural amino acids has been developed. The compounds synthesized have been tested for mutagenic activity on plant objects using the Allium test. It has been shown that the presence of a nitro group endows the compound with inhibitory property

  已经开发了一种高产率合成几种含有酰亚胺、环己烯和降冰片烯环以及天然氨基酸片段的羧酸酰胺的方法。合成的化合物已使用葱属试验测试了对植物对象的诱变活性。已经表明，硝基的存在赋予化合物抑制特性和诱导染色体重排的能力，而脂肪族碳链、甲基和吗啉片段的存在相反，赋予生长-调节特性而不引起诱变效应。该研究已经证实，由此产生的生物活性化合物对于在农业中的实际应用具有重要意义。
• Norbornene chaotropic salts as low molecular mass ionic organogelators (LMIOGs)
  作者：Jordan R. Engstrom、Aramballi J. Savyasachi、Marzieh Parhizkar、Alessandra Sutti、Chris S. Hawes、Jonathan M. White、Thorfinnur Gunnlaugsson、Frederick M. Pfeffer

  DOI：10.1039/c8sc01798k

  日期：——

  norbornene (9:Na) functions as a potent, low molecular-mass (MW = 333 Da) ionic organogelator with a minimum gelating concentration of 0.5 wt% in THF, i-PrOH, 1,4-dioxane and n-BuOH. Fibrous crystals form in the gel and X-ray crystallography identified a cation mediated helical assembly process controlled by the chirality of the phenylalanine. In addition to excellent gelating properties 9:Na readily

  苯丙氨酸官能降冰片烯（9：钠）用作一种有效的，低分子量质量（中号w ^ = 333道尔顿）的离子有机胶凝剂与在THF中，为0.5％（重量）的最小胶凝浓度我的i-PrOH，1,4-二恶烷和ñ - BuOH。凝胶中形成的纤维状晶体和X射线晶体学确定了由苯丙氨酸的手性控制的阳离子介导的螺旋组装过程。除了出色的胶凝特性外，9：Na还容易形成水性双相和三相体系。
• Bodtke; Otto, Hans-Hartwig, Pharmazie, 2005, vol. 60, # 11, p. 803 - 813
  作者：Bodtke、Otto, Hans-Hartwig

  DOI：——

  日期：——
• Synthesis and Biological Activity of Esters Based on Cycloalkenedicarboxylic Acids
  作者：A. A. Firstova、E. R. Kofanov、M. I. Kovaleva

  DOI：10.1134/s1068162023010089

  日期：2023.2
• General Synthesis of Unsymmetrical Norbornane Scaffolds as Inducers for Hydrogen Bond Interactions in Peptides^,
  作者：Christian P. R. Hackenberger、Ingo Schiffers、Jan Runsink、Carsten Bolm

  DOI：10.1021/jo030295+

  日期：2004.2.1

  Starting from readily accessible endo-cis-(2S,3R)-norbornene dicarboxylic acid benzyl monoester, a general and efficient synthetic approach toward unsymmetrical two-stranded peptidic structures was developed. In these structures the peptide strands are oriented in a parallel geometry. Their synthesis is easily applicable to a variety of amino acids and peptides. Specifically, a norbornane template as molecular scaffold induces hydrogen bonding between the adjacent peptide strands. The specific hydrogen bonding patterns between these strands were revealed by detailed NMR analysis including TOCSY/NOE experiments.