2,4,5-tris(benzyloxy)-β-nitrostyrene | 30223-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4,5-tris(benzyloxy)-β-nitrostyrene
• 英文别名: 2,4,5-Tribenzyloxy-β-nitro-styrol；2.4.5-Tribenzyloxy-β-nitrostyrrol；1-(2-Nitroethenyl)-2,4,5-tris(phenylmethoxy)benzene
• CAS: 30223-60-0
• 化学式: C₂₉H₂₅NO₅
• 分子量: 467.521
• InChiKey: YDIDJVWOJVQFTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4,5-tris(benzyloxy)-β-nitrostyrene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到2,4,5-tris(benzyloxy)phenetylamine
  参考文献：
  名称：

  Synthesis and Characterization of Models for the 2,4,5-Trihydroxyphenylalanine (TOPA)-Derived Cofactor of Mammalian Copper Amine Oxidases, and Initial Amine Reactivity Studies

  摘要：

  The mammalian copper amine oxidases effect the oxidative deamination of primary amines through utilization of an ''active carbonyl'' cofactor, shown recently to be the quinone form (TPQ) of a protein-based 2,4,5-trihydroxyphenylalanine (TOPA) residue. We synthesized three models for the cofactor in both reduced (benzenetriol) and oxidized (hydroxyquinone) forms, which differ in the nature of the alkyl substituent mimicking the connection to the protein backbone: hydantoinylmethyl, phthalimidoethyl, and pivalamidoethyl. The quinone forms were capable of deaminating benzylamine in aqueous CH3CN both stoichiometrically and catalytically (in the presence of O-2), but incapable of deaminating non-benzylic amines. In order to clarify the various reactions potentially occurring during aerobic autorecycling deamination, we studied the pH-dependent benzenetriol --> hydroxyquinone autoxidation as well as the possible reaction of amines with the benzenetriol forms. The latter undergo stoichiometric substitution with amines to give (alkylamino)resorcinols, not via cyclohexadienone tautomerization previously proposed, but via a redox cycling mechanism involving condensation of the amines with traces of hydroxyquinone present in the benzenetriol preparations. This observed substitution regiochemistry, as well as structural characterization of the hydroxyquinone arylhydrazine derivatives, confirms that amines react exclusively at the electrophilic C5 carbonyl position of TPQ models. Both the hydroxyquinone and benzenetriol forms were found to react with ethylenediamine in the presence of O-2 to give 6-hydroxy-7-(2-pivalamidoethyl)quinoxaline, consistent with the postulated generation of such moiety when lysyl oxidase is inactivated by ethylenediamine.

  DOI：

  10.1021/jo00088a023
• 作为产物：
  描述：

  硝基甲烷 、 2,4,5-三(苯甲氧基)苯甲醛 生成 2,4,5-tris(benzyloxy)-β-nitrostyrene
  参考文献：
  名称：

  General methods for the preparation of deuterium and tritium-labelled phenethylamines and phenethanollamines: Synthesis of radioactive 6-hydroxydopamine

  摘要：

  现已开发出一种制备用氘或氚标记的苯乙胺和苯乙醇胺的简便合成方法。将取代的苯甲醛与硝基甲烷或硝基乙烷缩合，然后用三硼化钠或硼氘化钠还原生成硝基苯乙烯。随后还原硝基并去除封端基团，得到在苄基位置含有氚或氘的苯乙胺或 a-甲基苯乙胺。取代的苯甲醛在低温下与硝基甲烷或硝基乙烷缩合，得到硝基乙醇，用琼斯试剂将其氧化成酮。用三硼化钠或氘化硼还原，然后还原硝基并去除阻断基团，得到苯乙醇胺或α-甲基苯乙醇胺，标记在苯甲基位置。制备氘代和/或三碘标记的 2,4,5-三羟基苯乙胺（6-羟基多巴胺）。α-甲基-6-羟基多巴胺、α-甲基对酪胺、β-苯乙胺。描述了 2-羟基苯乙醇胺和 α-甲基-4-苄氧基苯乙醇胺。

  DOI：

  10.1002/jlcr.2590110320

文献信息

• Modified syntheses of 2,4,5-trihydroxyphenylalanine, 2,4,5-trihydroxyphenethylamine, and analogs
  作者：Fred G. H. Lee、Donald E. Dickson、Albert A. Manian

  DOI：10.1021/jm00285a034

  日期：1971.3