4-amino-1,2-benzenediol diacetate | 71573-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-amino-1,2-benzenediol diacetate
• 英文别名: 4-aminobenzene-1,2-diol diacetate；3,4-Diacetoxyanilin；3,4-diacetoxy-aniline；4-Amino-brenzcatechin-diacetat；3,4-Diacetoxy-anilin；3,4-di(acetoxy)-aniline；4-Aminobenzene-1,2-diyl diacetate；(2-acetyloxy-4-aminophenyl) acetate
• CAS: 71573-24-5
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: JPBLUIHWOVGRCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-1,2-benzenediol diacetate 在 三光气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 3,4-diacetoxybenzoisocyanide
  参考文献：
  名称：

  Structure–Activity Relationship and Rational Design of 3,4-Dephostatin Derivatives as Protein Tyrosine Phosphatase Inhibitors

  摘要：

  Several alkyl- and O-methylated-3,3-dephostatin were synthesized and evaluated for their inhibitory activity toward protein tyrosine phosphatase. Alkyl chains with a length up to that of the pentyl group gave tolerable inhibition, whereas methylation of hydroxyl groups resulted in a decrease in the activity. Based on the structure-activity relationship and X-ray crystallographic analysis of C215S PTP1B-phosphotyrosine containing peptide complex, the mode of binding of 3,4-dephostatins to the active site was speculated with the aid of calculation. Several hydrogen bonds and CH/pi interactions were suggested to be important for inhibition of PTPase. A novel nitroso-free methoxime compound was designed so that all the attractive interactions were maintained. The methoxime compound was synthesized and shown to inhibit PTP1B. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01058-3
• 作为产物：
  描述：

  4-硝基儿茶酚 在 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 4-amino-1,2-benzenediol diacetate
  参考文献：
  名称：

  噻唑基邻苯二酚：染料敏化太阳能电池的吸电子邻苯二酚锚定基团。

  摘要：

  采用五元双齿螯合的锚定基团对于实现染料敏化太阳能电池（DSSC）的高功率转换效率（η）和长期耐久性具有吸引力。在这方面，我们选择了邻苯二酚作为可以采用螯合的锚定基团。但是，含邻苯二酚敏化剂的DSSC从未超过2％的η值。这些不良的光伏性能可能与邻苯二酚中羟基的供电子能力有关。考虑到这些，我们设想将吸电子的噻唑部分与邻苯二酚锚定基团融合将改善其光电性能。在本文中，我们报道了带有噻唑邻苯二酚锚定基团的推挽卟啉敏化剂ZnPTC。DSSC与ZnPTC表现出η＝ 4.87％。该值是基于邻苯二酚的DSSC报告的最高值。同时，尽管在苛刻的条件下仍具有强大的锚固性能，但长期电池的耐久性并未得到改善。

  DOI：

  10.1002/cphc.201900342

文献信息

• Silver-Catalyzed Radical Aminofluorination of Unactivated Alkenes in Aqueous Media
  作者：Zhaodong Li、Liyan Song、Chaozhong Li

  DOI：10.1021/ja400124t

  日期：2013.3.27

  We report herein a mild and catalytic intramolecular aminofluorination of unactivated alkenes. Thus, with the catalysis of AgNO3, the reactions of various N-arylpent-4-enamides with Selectfluor reagent in CH2Cl2/H2O led to the efficient synthesis of 5-fluoromethyl-substituted γ-lactams. A mechanism involving silver-catalyzed oxidative generation of amidyl radicals and silver-assisted fluorine atom

  我们在此报告了未活化烯烃的温和催化分子内氨基氟化。因此，在 AgNO3 的催化下，各种 N-芳基戊-4-烯酰胺与 Selectfluor 试剂在 CH2Cl2/H2O 中的反应导致 5-氟甲基取代的 γ-内酰胺的有效合成。提出了一种涉及银催化氧化产生酰胺基自由基和银辅助氟原子转移的机制。
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR THE TREATMENT OF AMYLOID DISEASES AND SYNUCLEINOPATHIES SUCH AS ALZHEIMER'S DISEASE, TYPE 2 DIABETES, AND PARKINSON'S DISEASE<br/>[FR] COMPOSES, COMPOSITIONS ET PROCEDES DE TRAITEMENT DE MALADIES AMYLOIDES ET DE SYNUCLEINOPATHIES, NOTAMMENT DE LA MALADIE D'ALZHEIMER, DU DIABETE DE TYPE 2 ET DE LA MALADIE DE PARKINSON
  申请人：PROTEOTECH INC

  公开号：WO2003101927A1

  公开（公告）日：2003-12-11

  Bis- and tris-dihydroxyaryl compounds and their methylenedioxy analogs and pharmaceutically acceptable esters, their synthesis, pharmaceutical compositions containing them, and their use in the treatment of amyloid diseases, especially Aß amyloidosis, such as observed in Alzheimer's disease, IAPP amyloidosis, such as observed in type 2 diabetes, and synucleinophathies, such as observed in Parkinson's disease, and the manufacture of medicaments for such treatment.

  双-和三-二羟基芳基化合物及其亚甲二氧基类似物和药用可接受酯，它们的合成，含有它们的药物组合物，以及它们在治疗淀粉样疾病，特别是Aß淀粉样病变，如阿尔茨海默病中观察到的，IAPP淀粉样病变，如2型糖尿病中观察到的，以及α-突触核病，如帕金森病中观察到的，以及用于制造用于此类治疗的药物。
• Synthetic catechol derivatives, method for production and use thereof
  申请人：Gruenenthal GmbH

  公开号：US06380181B1

  公开（公告）日：2002-04-30

  Catechol derivatives of general formula (I) in which R1 denotes O-acyl and R2 represents amino acid residues in the 3- and/or 4-position function as siderophores and/or as biological chelating agents for iron in gram-negative bacteria. Conjugates with antibiotics improve penetration into bacterial cells, thereby increasing antibacterial efficacy of the cells.

  通式（I）中的邻苯二酚衍生物，其中R1代表O-酰基，R2代表3-和/或4-位置的氨基酸残基，可作为革兰氏阴性细菌中铁的铁载体和/或生物螯合剂。与抗生素结合体能够提高穿透细菌细胞的能力，从而增加细胞的抗菌效果。
• Efficient Synthesis of 5,6-Dihydroxyindole Dimers, Key Eumelanin Building Blocks, by a Unified <i>o</i>-Ethynylaniline-Based Strategy for the Construction of 2-Linked Biindolyl Scaffolds
  作者：Luigia Capelli、Paola Manini、Alessandro Pezzella、Alessandra Napolitano、Marco d’Ischia

  DOI：10.1021/jo901259s

  日期：2009.9.18

  A unified convenient strategy for the synthesis of 5,6-dihydroxyindole-derived 2,7′-, 2,2′-, and 2,3′-biindolyls is reported, which is based on proper manipulation of key o-ethynylaniline precursors. By the same methodology 5,6-diacetoxy-7-iodoindole can also be obtained in good yield.

  报道了一种基于5,6-二羟基吲哚衍生的2,7'-，2,2'-和2,3'-二吲哚合成方便的统一策略，该策略基于对关键的邻乙炔基苯胺前体的正确处理。通过相同的方法，也可以良好的产率获得5，6-二乙酰氧基-7-碘吲哚。
• Heinisch; Mollmann; Tresselt, Arzneimittel-Forschung/Drug Research, 1994, vol. 44, # 3, p. 349 - 354
  作者：Heinisch、Mollmann、Tresselt、Willitzer

  DOI：——

  日期：——