5-bromo-3,4-dihydro-2,2,7,8-tetramethyl-2H-1-benzopyran-6-ol | 26363-99-5

• 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: 5-bromo-3,4-dihydro-2,2,7,8-tetramethyl-2H-1-benzopyran-6-ol
• 英文别名: 5-bromo-6-hydroxy-2,2,7,8-tetramethylchroman；5-bromo-2,2,7,8-tetramethyl-chroman-6-ol；5-bromo-2,2,7,8-tetramethylchroman-6-ol；5-bromo-2,2,7,8-tetramethyl-3,4-dihydrochromen-6-ol
• CAS: 26363-99-5
• 化学式: C₁₃H₁₇BrO₂
• 分子量: 285.181
• InChiKey: NYVOFBGUQUHOPM-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±42.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-3,4-dihydro-2,2,7,8-tetramethyl-2H-1-benzopyran-6-ol 、 3,4-二甲氧基苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以89%的产率得到5-(3,4-Dimethoxy-phenylethynyl)-2,2,7,8-tetramethyl-chroman-6-ol
  参考文献：
  名称：

  Chroman / catechol杂种：合成和评估其抗氧化应激诱导的细胞损伤的活性。

  摘要：

  合成了三类在邻苯二酚衍生物在2或5位取代的苯并二氢吡喃，并研究了它们对氧化应激诱导的细胞损伤的活性。具体来说，使用单细胞凝胶电泳（彗星试验）评估了新分子保护培养的细胞免受H（2）O（2）诱导的DNA损伤的能力，而新化合物针对氧化应激诱导的神经保护活性被编程使用谷氨酸-challanged海马HT22细胞研究了细胞死亡。大多数新化合物比槲皮素具有更强的神经保护作用。5-取代的苯并二氢吡喃类似物，例如咖啡酰胺12和16和二氢二苯乙烯类似物24，分别对Jurkat T细胞和HT22细胞中H（2）O（2）-和谷氨酸诱导的损伤最有效。

  DOI：

  10.1021/jm0506120
• 作为产物：
  描述：

  2,3-二甲基氢醌 在 甲酸 、 硫酸 、 溴 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.33h， 生成 5-bromo-3,4-dihydro-2,2,7,8-tetramethyl-2H-1-benzopyran-6-ol
  参考文献：
  名称：

  Novel tocopherol derivatives. Part 32: On the bromination of pyrano[3,2-f]chromenes related to γ-tocopherol

  摘要：

  While bromination of gamma-tocopherol (2) with elemental bromine affords 5-bromo-gamma-tocopherol quantitatively (3), the analogous reaction of its truncated model compound, 2,2,7,8-tetramethylchromanol (2a) is known to be accompanied by side reactions and to produce hitherto unknown byproducts. These compounds originate from pyrano[3,2-f]chromene (6), a byproduct in the synthesis of model compound 2a, which affords bromochromene 7 as the major product. The reaction mechanism was shown to proceed via chromene 8 and its 1,2-dibromo addition compound 9, which eliminates HBr in an E1 process to finally afford 7. Analytical data including crystal structures of both 6 and 7 are reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.070

文献信息

• Bromination of Non-α-Tocopherols: A Comparative Synthetic, Kinetic and Computational Study
  作者：Anjan Patel、Stefan Böhmdorfer、Andreas Hofinger、Thomas Netscher、Thomas Rosenau

  DOI：10.1002/ejoc.200900495

  日期：2009.10

  the 5a-bromo derivative by an oxidation/addition mechanism via the corresponding o-quinone methide becomes a competitive process. By measurement of product ratios at different temperatures, the relative and absolute activation energies of the reaction systems with parallel reactions going on (β- and δ-tocopherol) were established. The kinetic data were in very good agreement with DFT results that showed

  广泛研究了三种非 α-生育酚及其截短的模型化合物在非极性溶剂中的溴化化学，并与 α-同类物的溴化化学进行了比较。溴化发生在所有非α-生育酚的游离芳香位置。在 δ-生育酚的情况下，C-5 优先于 C-7。在 5-甲基取代基的存在下，如在 β-生育酚中，通过氧化/加成机制通过相应的邻醌甲基化物形成 5a-溴衍生物成为一个竞争过程。通过测量不同温度下的产物比率，建立了平行反应（β-和δ-生育酚）的反应体系的相对活化能和绝对活化能。动力学数据与 DFT 结果非常吻合，DFT 结果表明 δ-生育酚溴化的产物比率与阳离子溴化中间体的稳定性相关。所有产品都经过全面表征，提供可靠的分析标准和参考化合物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Chroman derivatives
  申请人：Wang Bing

  公开号：US20050065150A1

  公开（公告）日：2005-03-24

  The invention relates to novel chroman derivatives, stereoisomers and pharmaceutically acceptable salts of Formula I wherein the substituents are as defined in the specification. They are useful in the treatment of disorders mediated by lipoxygenase, such as immune diseases, respiratory diseases and cardiovascular diseases, as well as in the treatment of neurodegenerative disorders and/or mitochondrial disorders. They are also useful in the manufacture of pharmaceutical formulations for the treatment of such conditions.

  本发明涉及新型的色甘醇衍生物、立体异构体和公认的药物盐，其化学式为I式，其中取代基如规范中所定义。它们可用于治疗通过脂氧合酶介导的疾病，如免疫性疾病、呼吸系统疾病和心血管疾病，以及神经退行性疾病和/或线粒体疾病的治疗。它们还可用于制造用于治疗这些疾病的药物制剂。
• CHROMAN DERIVATIVES
  申请人：WANG Bing

  公开号：US20120088783A1

  公开（公告）日：2012-04-12

  The invention relates to novel chroman derivatives, stereoisomers and pharmaceutically acceptable salts of Formula I wherein the substituents are as defined in the specification. They are useful in the treatment of disorders mediated by lipoxygenase, such as immune diseases, respiratory diseases and cardiovascular diseases, as well as in the treatment of neurodegenerative disorders and/or mitochondria) disorders. They are also useful in the manufacture of pharmaceutical formulations for the treatment of such conditions.

  本发明涉及新型的色甘醇衍生物、立体异构体及其在药学上可接受的盐，其化学式为I，其中置换基如规范中所定义。它们可用于治疗通过脂氧合酶介导的疾病，如免疫性疾病、呼吸系统疾病和心血管疾病，以及神经退行性疾病和/或线粒体疾病的治疗。它们也可用于制造用于治疗此类疾病的药物制剂。
• Bromination of α-tocopherol methano-dimer and ethano-dimer
  作者：Thomas Rosenau、Christian Adelwöhrer、Elisabeth Kloser、Kurt Mereiter、Thomas Netscher

  DOI：10.1016/j.tet.2005.11.050

  日期：2006.2

  Bromination of the ethano-dimer of alpha-tocopherol (6) afforded pyrano-spirodimer of alpha-tocopherol (7) quantitatively, while the methano-dimer of alpha-tocopherol (10) produced a mixture of products, including the furano-spirodimer 11, pyrano-spirodimer 7, and 5-bromo-gamma-tocopherol (12), the latter two formed in ail unusual dealkylative fragmentation step. The mechanisms were studied by a combination of trapping reactions as well as kinetic and computational studies. (c) 2005 Elsevier Ltd. All rights reserved.
• US7514461B2
  申请人：——

  公开号：US7514461B2

  公开（公告）日：2009-04-07