3-methyl-3-(4'-methylpent-3'enyl)-3H-naphtho<2,1-b>pyran-9-ol | 54246-36-5

• 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-ol
• 英文别名: 9-hydroxy-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-ol；3-Methyl-3-(4-methylpent-3-enyl)benzo[f]chromen-9-ol
• CAS: 54246-36-5
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: DQVWVJCNJKOKPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  3-methyl-3-(4'-methylpent-3'enyl)-3H-naphtho<2,1-b>pyran-9-ol 在 sodium dithionite 、 adogen 464 、 potassium nitrososulfonate 、 t-butoxide 、 氧气 、 potassium carbonate 作用下， 以 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：

  3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho<2,1-b>pyran-9-yl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-methyl-3-(4'-methylpent-3'enyl)-3H-naphtho<2,1-b>pyran-9-ol
  参考文献：
  名称：

  Antiviral Agents. I. Synthesis and Antiviral Evaluation of Trimeric Naphthoquinone Analogues of Conocurvone

  摘要：

  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。

  DOI：

  10.1071/ch08177

文献信息

• <i>ortho</i>-Quinone Methide Cyclizations Inspired by the Busseihydroquinone Family of Natural Products
  作者：Laura Burchill、Henry P. Pepper、Christopher J. Sumby、Jonathan H. George

  DOI：10.1021/acs.orglett.9b03060

  日期：2019.10.18

  A series of cascade reactions of o-quinone methides have been developed based on the proposed biosynthesis of busseihydroquinone and parvinaphthol meroterpenoid natural products. The polycyclic framework of the most complex family members, busseihydroquinone E and parvinaphthol C, was assembled by an intramolecular [4 + 2] cycloaddition of an electron-rich chromene substrate. The resultant cyclic enol

  基于所提出的丁二氢醌和对乙酰氨基酚类胡萝卜素天然产物的生物合成，已经开发了一系列邻甲基苯甲酸酯的级联反应。最复杂的家族成员多环氢醌E和对乙酰氨基酚C的多环骨架是通过分子内[4 + 2]富电子的苯烯底物的环加成组装而成的。所得的环状烯醇醚在酸性或氧化性条件下进行了重排，从而导致了类固醇D的新的全合成。
• 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.
• Regiospecific Synthesis of 2,3-Bisnaphthopyranyl Quinones Related to Conocurvone. Effect of Substituents on Palladium-Catalyzed Cross-Coupling of Organostannanes to Naphthopyranyl Hydroxyquinone Triflates
  作者：Kenneth W. Stagliano、Helena C. Malinakova

  DOI：10.1021/jo990785v

  日期：1999.10.1
• 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。