2,4,5-三(苯甲氧基)苯甲醛 | 7298-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2,4,5-三(苯甲氧基)苯甲醛
• 英文名称: 2,4,5-tribenzyloxybenzaldehyde
• 英文别名: 2,4,5-Tris(benzyloxy)benzaldehyde；2,4,5-tris(phenylmethoxy)benzaldehyde
• CAS: 7298-35-3
• 化学式: C₂₈H₂₄O₄
• 分子量: 424.496
• InChiKey: YCXDJYMGMZGUPY-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  618.2±50.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4,5-三(苯甲氧基)苯甲醛 在 lithium aluminium tetrahydride 、 三溴化磷 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 5-(2-氨基乙基)苯-1,2,4-三醇盐酸盐
  参考文献：
  名称：

  2,4,5-三羟基苯丙氨酸（6-羟基多巴）的合成。一种中枢性去甲肾上腺素消耗剂。

  摘要：

  DOI：

  10.1021/jm00303a028
• 作为产物：
  描述：

  1,2,4-三苄氧基苯 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 16.0h， 以71%的产率得到2,4,5-三(苯甲氧基)苯甲醛
  参考文献：
  名称：

  Stereoselective Syntheses of (-)-Podorhizol Lignan and its Derivatives:erythroandthreoPreferential Aldol Condensation of Potassium Enolate from γ-Butyrolactone with Alkoxybenzaldehyde

  摘要：

  (-)-Podorhizol (1) 是通过 3,4,5-三甲氧基苯甲醛与来自 (+)-(R)-3-(3,4-二氧基苯甲基)-4-丁内酯 (2) 的钾烯醇进行红脆优先的醇缩合反应立体选择性合成的（红脆:反式=85:15）。在许多烷氧基苯甲醛与来自 (+)-γ-丁内酯 2 的钾烯醇的醇缩合反应中观察到了红脆选择性。然而，具有在 2 和 6 位均为甲氧基取代基的苯甲醛在与来自 (+)-γ-丁内酯 2 的钾烯醇的醇缩合反应中则表现出反式选择性。

  DOI：

  10.1271/bbb.63.1453

文献信息

• Synthesis and spectroscopic characterization of model compounds for the active site cofactor in copper amine oxidases
  作者：Minae Mure、Judith P. Klinman

  DOI：10.1021/ja00069a008

  日期：1993.8

  The synthesis and spectroscopic characterization of compounds which model different forms of the active site cofactor in copper amine oxidases have been pursued. As described, 5-(2,4,5-trihydroxybenzyl)hydantoin (1 red H 3 ), its corresponding quinone (1 ox H), and 6-amino-4-ethylresorcinol (7H 2 ) have been prepared. Additionally, 5-(3,4-dihydroxybenzyl)hydantoin (2 red H 2 ) was synthesized for comparative

  已经进行了模拟铜胺氧化酶中不同形式的活性位点辅因子的化合物的合成和光谱表征。如上所述，已经制备了 5-(2,4,5-三羟基苄基) 乙内酰脲 (1 red H 3 )、其相应的醌 (1 ox H) 和 6-氨基-4-乙基间苯二酚 (7H 2 )。此外，还合成了 5-(3,4-二羟基苄基) 乙内酰脲 (2 red H 2 ) 用于比较目的
• General methods for the preparation of deuterium and tritium-labelled phenethylamines and phenethanollamines: Synthesis of radioactive 6-hydroxydopamine
  作者：A. Rotman、J. W. Daly、C. R. Creveling

  DOI：10.1002/jlcr.2590110320

  日期：——

  A convenient synthetic method for preparation of phenethylamines and phenethanolamines labeled with deuterium or tritium has been developed. A substituted benzaldedyde is condensed with nitromethane or nitroethane and the resultant nitrostyrene is reduced with sodium borotritide or borodeuteride. Subsequent reduction of the nitro-group and removal of blocking groups yields a phenethylamine or an a-methylphenethylamine containing a tritium or deuterium in the benzylic position. Condensation of the substituted benzaldehyde with nitromethane or nitroethane at low temperature yields a nitroalcohol which is oxidized to a ketone with Jones reagent. Reduction with sodium borotritide or borodeuteride and subsequent reduation of the nitro-group and removal of blocking groups yields a phenethanolamine or α-methylphenethanolamine labeled in the bensylic position. Preparation of deutero- and/or tritio-labeled 2,4,5-trihydroxyphenethylamine (6-hydroxydopamine). α-methyl-6-hydroxydopamine, α-methyl-p-tyramine, β-phenethanolamine. 2-hydroxyphenethanolamine and α-methyl-4-benzyloxyphenethanolamine is described.

  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。
• 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
• Synthesis and Characterization of Models for the 2,4,5-Trihydroxyphenylalanine (TOPA)-Derived Cofactor of Mammalian Copper Amine Oxidases, and Initial Amine Reactivity Studies
  作者：Fengjiang Wang、Jin-Young Bae、Alan R. Jacobson、Younghee Lee、Lawrence M. Sayre

  DOI：10.1021/jo00088a023

  日期：1994.5

  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.
• BHAT, G. A.;DICKSON, D. E., MONATSH. CHEM., 1984, 115, N 1, 113-116
  作者：BHAT, G. A.、DICKSON, D. E.

  DOI：——

  日期：——