2-hydroxy-7-methoxy-5-methyl-4-(4-nitrophenyl)-cyclohepta-2,4,6-trienone | 1414861-25-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 2-hydroxy-7-methoxy-5-methyl-4-(4-nitrophenyl)-cyclohepta-2,4,6-trienone
• 英文别名: 2-hydroxy-7-methoxy-5-methyl-4-(4-nitrophenyl)cyclohepta-2,4,6-trienone；2-Hydroxy-3-methoxy-5-methyl-6-(4-nitrophenyl)cyclohepta-2,4,6-trien-1-one；2-hydroxy-3-methoxy-5-methyl-6-(4-nitrophenyl)cyclohepta-2,4,6-trien-1-one
• CAS: 1414861-25-8
• 化学式: C₁₅H₁₃NO₅
• 分子量: 287.272
• InChiKey: KRGZVRFZNMKGBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-7-methoxy-5-methyl-4-(4-nitrophenyl)-cyclohepta-2,4,6-trienone 在 氢溴酸 、 溶剂黄146 作用下， 反应 3.0h， 以17.8 mg的产率得到2,7-dihydroxy-4-methyl-5-(4-nitrophenyl)cyclohepta-2,4,6-trienone
  参考文献：
  名称：

  An Oxidopyrylium Cyclization/Ring-Opening Route to Polysubstituted α-Hydroxytropolones

  摘要：

  alpha-Hydroxytropolones are a class of molecules with therapeutic potential against several human diseases. However, structure-activity relationship studies on these molecules have been limited due to a scarcity of efficient synthetic methods to access them. It is demonstrated herein that alpha-hydroxytropolones can be generated through a BCl3-mediated ring-opening/aromatization/demethylation process on 8-oxabicyclo[3.2.1]octenes. Used in conjunction with an improved method based on established oxidopyrylium dipolar cycloadditions, several polysubstituted alpha-hydroxytropolones can be accessed in three steps from readily available alpha-hydroxy-gamma-pyrones.

  DOI：

  10.1021/ol302892g
• 作为产物：
  描述：

  3-methoxy-5-methyl-6-(4-nitrophenyl)-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one 在 三氟甲磺酸 作用下， 以 氘代氯仿 为溶剂， 反应 0.5h， 以95%的产率得到2-hydroxy-7-methoxy-5-methyl-4-(4-nitrophenyl)-cyclohepta-2,4,6-trienone
  参考文献：
  名称：

  三氟甲磺酸介导的 3-甲氧基-8-氧杂双环[3.2.1]八-3,6-二烯-2-酮的重排：甲氧基托酚酮和呋喃的合成

  摘要：

  甲氧基托酚酮是用于治疗开发的有用支架，因为其已知的生物活性和在 α-羟基托酚酮合成中的确定价值。用三氟甲磺酸处理后，一系列 3-甲氧基-8-氧杂二环[3.2.1]八-3,6-二烯-2-酮快速而干净地重排，形成甲氧基托酚酮。有趣的是，衍生自乙炔二甲酸二甲酯（R 2 = R 3 = CO 2 Me）的自行车反而形成呋喃作为主要产物。

  DOI：

  10.1021/jo401617r

文献信息

• [EN] HYDROXYLATED TROPOLONE INHIBITORS OF NUCLEOTIDYL TRANSFERASES IN HERPESVIRUS AND HEPATITS B AND USES THEREFOR<br/>[FR] INHIBITEURS HYDROXYLÉS DE TROPOLONE DE NUCLÉOTIDYL-TRANSFÉRASES UTILISÉS DANS LE TRAITEMENT DU VIRUS DE L'HERPÈS ET DE L'HÉPATITE B ET LEURS UTILISATIONS
  申请人：UNIV SAINT LOUIS

  公开号：WO2016201243A1

  公开（公告）日：2016-12-15

  The present disclosure relates to inhibitors of herpesvirus nucleic acid metabolism and inhibitors of Hepatitis B virus. Also provided are methods of treatment using these agents.

  本公开涉及抑制疱疹病毒核酸代谢和乙型肝炎病毒的抑制剂。还提供了使用这些药剂的治疗方法。
• An Oxidopyrylium Cyclization/Ring-Opening Route to Polysubstituted α-Hydroxytropolones
  作者：Christine Meck、Noushad Mohd、Ryan P. Murelli

  DOI：10.1021/ol302892g

  日期：2012.12.7

  alpha-Hydroxytropolones are a class of molecules with therapeutic potential against several human diseases. However, structure-activity relationship studies on these molecules have been limited due to a scarcity of efficient synthetic methods to access them. It is demonstrated herein that alpha-hydroxytropolones can be generated through a BCl3-mediated ring-opening/aromatization/demethylation process on 8-oxabicyclo[3.2.1]octenes. Used in conjunction with an improved method based on established oxidopyrylium dipolar cycloadditions, several polysubstituted alpha-hydroxytropolones can be accessed in three steps from readily available alpha-hydroxy-gamma-pyrones.
• Triflic Acid-Mediated Rearrangements of 3-Methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: Synthesis of Methoxytropolones and Furans
  作者：Yvonne D. Williams、Christine Meck、Noushad Mohd、Ryan P. Murelli

  DOI：10.1021/jo401617r

  日期：2013.12.6

  because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that are derived from dimethyl acetylenedicarboxylate (R2 = R3 = CO2Me) instead form furans as the major product.

  甲氧基托酚酮是用于治疗开发的有用支架，因为其已知的生物活性和在 α-羟基托酚酮合成中的确定价值。用三氟甲磺酸处理后，一系列 3-甲氧基-8-氧杂二环[3.2.1]八-3,6-二烯-2-酮快速而干净地重排，形成甲氧基托酚酮。有趣的是，衍生自乙炔二甲酸二甲酯（R 2 = R 3 = CO 2 Me）的自行车反而形成呋喃作为主要产物。