3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho<2,1-b>pyran-9-yl acetate | 55181-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho<2,1-b>pyran-9-yl acetate
• 英文别名: 9-acetoxy-3-methyl-(4-methylpent-3-enyl)-3H-naphtho[2,1-b]pyran；(+/-)-3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho[2,1-b]pyran-9-yl acetate；9-acetoxy-3-methyl-3-(4-methyl-pent-3-enyl)-3H-benzo[f]chromene；[3-Methyl-3-(4-methylpent-3-enyl)benzo[f]chromen-9-yl] acetate
• CAS: 55181-96-9
• 化学式: C₂₂H₂₄O₃
• 分子量: 336.431
• InChiKey: ZEUUJMRMCMIOOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho<2,1-b>pyran-9-yl acetate 在 sodium dithionite 、 adogen 464 、 potassium nitrososulfonate 、 t-butoxide 、 氧气 、 碳酸氢钠 、 potassium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 生成 (+/-)-9-hydroxy-3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho[2,1-b]pyran-7,10-dione
  参考文献：
  名称：

  Kinetic Resolution of Racemic Chromenes via Asymmetric Epoxidation: Synthesis of (+)-Teretifolione B

  摘要：

  DOI：

  10.1021/jo00122a008
• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 4-甲基吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho<2,1-b>pyran-9-yl acetate
  参考文献：
  名称：

  Synthesis of various 2H-benzopyran compounds and their kinetic resolution by asymmetric hydrolysis of their racemic acetates mediated by lipases

  摘要：

  The preparation of 2H-benzopyrans from bromophenols and tertiary allylic alcohols is described. The reaction is characterised by its mildness, good yields and ease of work-up. Kinetic resolution of the latter up to 95% ee was obtained by using enzyme-catalysed enantioselective hydrolysis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00176-2

文献信息

• Antiviral Agents. I. Synthesis and Antiviral Evaluation of Trimeric Naphthoquinone Analogues of Conocurvone
  作者：Ian T. Crosby、Mark L. Rose、Maree P. Collis、Paula J. de Bruyn、Philip L. C. Keep、Alan D. Robertson

  DOI：10.1071/ch08177

  日期：——

  Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity.

  Conocurvone 是一种从澳大利亚特有灌木 Conosperum sp.（原生植物科）中分离出来的新型天然产物，具有抗艾滋病毒的活性，但它是一种高亲脂性化合物，这表明它的水溶性和生物利用度可能存在问题。本文介绍了一种利用 2-羟基萘醌和 2,3-二卤醌缩合合成三聚萘醌的通用简便方法。报告还介绍了应用这种方法合成一系列更简单、亲油性更低的三聚萘醌简单类似物 conocurvone 及其抗 HIV 活性。
• Biomimetic Synthetic Studies on the Bruceol Family of Meroterpenoid Natural Products
  作者：Aaron J. Day、Christopher J. Sumby、Jonathan H. George

  DOI：10.1021/acs.joc.9b02862

  日期：2020.2.21

  The key step in the synthesis of both bruceol and isobruceol was an intramolecular hetero-Diels-Alder reaction of an o-quinone methide that was formed by dearomatization of an electron-rich chromene. The synthesis of an elusive biosynthetic intermediate also allowed a concise synthesis of eriobrucinol via a photochemical [2 + 2] cycloaddition. Furthermore, some speculation on the biosynthesis of prenylated

  仿生方法进行全合成可以带来许多好处，包括开发级联反应以快速产生分子复杂性，以及指导旧天然产物的结构修订和新产物的预期。在本文中，我们描述了布鲁索醇（一种五环戊二烯类萜）的仿生合成如何导致异bruceol的预期，分离和合成。布鲁索尔和异丁烯醇的合成中的关键步骤是邻苯二甲酰亚胺的分子内异狄尔斯-阿尔德反应，该反应是通过富电子的苯并二甲苯脱芳香化反应而形成的。难以捉摸的生物合成中间体的合成还允许通过光化学[2 + 2]环加成法精确合成芥酸紫丁香酚。此外，关于烯丙基化芥蓝醇衍生物的生物合成的一些推测激发了Claisen / Cope / Diels-Alder级联反应的发展。我们还报告了使用单线态氧烯反应生成卤代布鲁索尔衍生物和几种原溴苯酚天然产物的合成方法。
• Constituents of Conospermum brachyphyllum. Improved Methods for the Isolation and Synthesis of (+)-Conocurvone and the Structure of (+)-Brachyphyllone
  作者：James A. Armstrong、Robert W. Baker、Wayne M. Best、Lindsay T. Byrne、Jack R. Cannon、Steven M. Colegate、Anthony R. Gray、Neville G. Marchant、Neil Rothnie、Melvyn V. Sargent、Colette G. Sims、Zdzislaw E. Spadek、Robert D. Trengove

  DOI：10.1071/c98143

  日期：——

  Improved methods have been devised for the isolation of (+)-conocurvone (1) from the roots of Conospermum brachyphyllum Lindl. and for its synthesis. The isolation of (R)-(+)-9-hydroxy-3-(4′-hydroxy-4′-methylpentan-1′-yl)-3,8-dimethyl-3H-naphtho[2,1-b]pyran-7,10-dione [(+)-brachyphyllone] (2), a minor constituent of this species, its structural elucidation and partial synthesis are also described. 8-C-Methylteretifolione-B (9) and 8-C-methyl-9-O-methylteretifolione-B (10), as well as the previously isolated (+)-teretifolione-B (8), also occur in this plant.

  从 Conospermum brachyphyllum Lindl. (1) 的改进方法。 及其合成的改进方法。分离出 (R)-(+)-9-hydroxy-3-(4′-hydroxy-4′-methylpentan-1′-yl)-3,8-dimethyl-3H-naphtho[2,1-b]pyran-7,10-dione (+)-brachyphyllone](2)，该物种的一种次要成分、 还介绍了其结构阐明和部分合成。 8-C-Methylteretifolione-B (9) 和 8-C-甲基-9-O-甲基三乙酮-B（10）以及 之前分离出的 (+)-teretifolione-B (8)，也出现在这种植物中。 植物中。
• Synthesis of various 2H-benzopyran compounds and their kinetic resolution by asymmetric hydrolysis of their racemic acetates mediated by lipases
  作者：J.Y Goujon、F Zammattio、B Kirschleger

  DOI：10.1016/s0957-4166(00)00176-2

  日期：2000.6

  The preparation of 2H-benzopyrans from bromophenols and tertiary allylic alcohols is described. The reaction is characterised by its mildness, good yields and ease of work-up. Kinetic resolution of the latter up to 95% ee was obtained by using enzyme-catalysed enantioselective hydrolysis. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Kinetic Resolution of Racemic Chromenes via Asymmetric Epoxidation: Synthesis of (+)-Teretifolione B
  作者：Susan L. Vander Velde、Eric N. Jacobsen

  DOI：10.1021/jo00122a008

  日期：1995.9