6-acetoxy-2,5,7,8-tetramethylchromane-2-carboxylic acid | 122005-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-acetoxy-2,5,7,8-tetramethylchromane-2-carboxylic acid
• 英文别名: 6-acetoxy-2,5,7,8-tetramethylchroman-2-carboxylic acid；6-acetoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid；6-acetyloxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid
• CAS: 122005-20-3
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: CUHJERIEOYEEOS-UHFFFAOYSA-N

物化性质

• 沸点：
  445.7±45.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-acetoxy-2,5,7,8-tetramethylchromane-2-carboxylic acid 在 sodium hydroxide 、 二氯磷酸苯酯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 6-hydroxy-2,5,7,8-tetramethyl-N-phenyl-3,4-dihydro-2H-1-benzopyran-2-carboxamide
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of N-(aza)arylcarboxamides derived from Trolox®

  摘要：

  A series of 6-(aza) arylmethoxychroman-2-carboxamides 22-38, derived from Trolox(R) or 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, was prepared using two strategies, i.e. phenol blockade was carried out before or after amidification. These compounds were evaluated against peripheral inflammation by a carrageenin-induced foot-pad edema test. A permanent blockade of the phenol function by arylmethoxy groupings, in particular by the quinolylmethoxy moiety, was generally detrimental to activity; only the 6-benzyloxy and quinolylmethoxy derivatives 22 and 31 exhibited significant inhibition (58.3 and 97.1%) after oral administration of 0.4 mmol kg(-1). Among their 6-acetoxy or 6-hydroxy precursors 12-21, evaluated at 0.4 and 0.1 mmol kg(-1), the N-(4-pyridyl) chromancarboxamides 15 and 20 exerted the highest inhibitory activity. Their ID50 were 14.7 +/- 5.5 mg kg(-1) and 14.7 +/- 4.5 mg kg(-1), respectively. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80065-2
• 作为产物：
  描述：

  奎诺二甲基丙烯酸酯 在 盐酸 、 乙酸酐 作用下， 以 吡啶 、 水 为溶剂， 生成 6-acetoxy-2,5,7,8-tetramethylchromane-2-carboxylic acid
  参考文献：
  名称：

  Benzopyran compounds

  摘要：

  从式I中选择的化合物组中选择的化合物##STR1##其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5，R.sub.6，R.sub.7，X和n在描述中定义，其光学异构体，以及其与药学上可接受的酸或碱的加成盐。药物产品，用于治疗或预防由于或与过氧化现象和前列腺素生物合成的干扰有关的疾病。

  公开号：

  US05315017A1

文献信息

• Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters
  作者：Adam Noble、Riccardo S. Mega、Daniel Pflästerer、Eddie L. Myers、Varinder K. Aggarwal

  DOI：10.1002/anie.201712186

  日期：2018.2.19

  The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single-electron reduction of an α-boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α-amino, α-oxy, and

  描述了通过将羧酸直接脱羧基加成到乙烯基硼酸酯上来合成烷基硼酸酯。该反应在温和的光氧化还原催化下进行，涉及α-硼基自由基中间体前所未有的单电子还原成相应的阴离子。该反应适用于多种底物，包括α-氨基、α-氧基和烷基羧酸，从而提供了一种快速获取具有潜在生物学重要性的含硼分子的新方法。
• Decarboxylative Conjunctive Cross‐coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis
  作者：Riccardo S. Mega、Vincent K. Duong、Adam Noble、Varinder K. Aggarwal

  DOI：10.1002/anie.201916340

  日期：2020.3.9

  The synthesis of complex alkyl boronic esters through conjunctive cross-coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross-coupling cascade of vinyl boronic esters. Excellent functional-group tolerance is displayed, and application of

  描述了通过乙烯基硼酸酯与羧酸和芳基碘化物的联合交叉偶联合成复杂的烷基硼酸酯。该反应在温和的金属光氧化还原条件下进行，并涉及乙烯基硼酸酯的前所未有的脱羧自由基加成/交叉偶联级联。显示出优异的官能团耐受性，并且一系列羧酸（包括仲 α-氨基酸和芳基碘）的应用提供了获得高度官能化烷基硼酸酯的有效途径。脱羧结合交叉偶联也应用于景天生物碱的合成。
• Antioxidant chroman compounds
  申请人：Hoffman-La Roche Inc.

  公开号：US03947473A1

  公开（公告）日：1976-03-30

  The (6-hydroxy-chroman-2-yl) acetic or carboxylic acid derivatives useful as antioxidants and a method for preparing these derivatives from hydroquinones and intermediates in this synthesis as well as the use of these derivatives as intermediates in the preparation of optically active alpha-tocopherol.

  (6-羟基-色苷-2-基) 乙酸或羧酸衍生物可用作抗氧化剂，以及从对苯二酚和合成中间体制备这些衍生物的方法，以及在制备光学活性α-生育酚中使用这些衍生物作为中间体。
• 4-(p-QUINONYL)-2-HYDROXYBUTANAMIDE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES
  申请人：Jankowski Orion D.

  公开号：US20090118257A1

  公开（公告）日：2009-05-07

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, and stroke (MELAS), Kearns-Sayre Syndrome (KSS), are disclosed, as well as compounds useful in the methods of the invention, such as 4-(p-quinolyl)-2-hydroxybutanamide derivatives. Methods and compounds useful in treating other disorders such as amyotrophic lateral sclerosis (ALS), Huntington's disease, Parkinson's disease, and pervasive developmental disorders such as autism are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  揭示了治疗或抑制线粒体疾病的方法，例如弗里德雷希共济失调症（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒和中风（MELAS）、科恩斯-萨耶综合征（KSS），以及在本发明方法中有用的化合物，如4-(对喹啉基)-2-羟基丁酰胺衍生物。还揭示了用于治疗其他疾病的方法和化合物，如肌萎缩侧索硬化症（ALS）、亨廷顿病、帕金森病和广泛性发展障碍如自闭症。还揭示了用于评估受试者代谢状态和治疗疗效的能量生物标志物。还揭示了调节、规范或增强能量生物标志物的方法，以及用于这些方法的化合物。
• Second generation of α-tocopherol analogs-nitric oxide donors: Synthesis, physicochemical, and biological characterization
  作者：Gloria V. López、Fabiana Blanco、Paola Hernández、Ana Ferreira、Oscar E. Piro、Carlos Batthyány、Mercedes González、Homero Rubbo、Hugo Cerecetto

  DOI：10.1016/j.bmc.2007.06.019

  日期：2007.9

  mimetics with NO-releasing capacity are reported. The selected NO-donor moieties were nitrooxy and furoxan. All products were tested for their in vitro NO-releasing capacities, vasodilating properties and mammal cytotoxic activities. The lipophilic-hydrophilic balance of all products was also evaluated. A new hybrid furoxan, phenol derivative 17, possesses adequate profile of the studied properties.

  报道了一系列具有NO释放能力的α-生育酚模拟物的合成，物理化学和生物学特性。所选的NO供体部分是硝基氧基和呋喃喃。测试了所有产品的体外NO释放能力，血管舒张特性和哺乳动物细胞毒性活性。还评估了所有产品的亲脂-亲水平衡。一种新的杂氧呋喃杂酚衍生物，苯酚衍生物17，具有足够的研究性质。