(+/-)-9-hydroxy-3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho[2,1-b]pyran-7,10-dione | 166376-67-6

• 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: (+/-)-9-hydroxy-3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho[2,1-b]pyran-7,10-dione
• 英文别名: (±)-teretifolione B；teretifolione B
• CAS: 166376-67-6
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: LCORMMZDCPNNTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3-二溴-1,4-萘醌 、 (+/-)-9-hydroxy-3-methyl-3-(4'-methylpent-3'-enyl)-3H-naphtho[2,1-b]pyran-7,10-dione 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到(+/-)-8-(3'-bromo-1',4'-dioxo-1',4'-dihydronaphthalen-2'-yl)-9-hydroxy-3-methyl-3-(4'-methylpent-3'-yl)-3H-naphtho[2,1-b]pyran-7,10-dione
  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
• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 4-甲基吡啶 、 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

文献信息

• Asymmetric total syntheses of teretifolione B and methylteretifolione B via Diels-Alder reaction of optically active pyranobenzyne and substituted furans
  作者：Kazuaki Katakawa、Mika Kainuma、Katsuya Suzuki、Saori Tanaka、Takuya Kumamoto

  DOI：10.1016/j.tet.2017.06.050

  日期：2017.8

  report the asymmetric total syntheses of teretifolione B and methylteretifolione B, which are benzochromenes originally isolated from Conospermum plants. The synthesis involves enzymatic asymmetric transesterification of racemic acetoxychromene and construction of the basic framework via Diels-Alder reaction of optically active pyranobenzyne and substituted furans. The absolute configuration of the chiral

  我们报告了teretifolione B和甲基teretifolione B，这是最初从Conospermum植物中分离出的苯并二氢萘酮的不对称总合成。合成涉及外消旋乙酰氧基苯二酚的酶促不对称酯交换反应和通过光学活性吡喃苯并呋喃和取代的呋喃的Diels-Alder反应构建基本骨架。手性色烯的绝对构型是通过对苯替利酮B的不对称全合成及其表征来明确确定的。以相似的方式完成了甲基叔丁基叶酮B的第一个不对称全合成，并建立了其绝对构型，尚未报道其绝对证据。
• A New Method for the Synthesis of 2-Hydroxy-3-nitro-1,4-naphthoquinones:  Application to Regiospecific Preparation of Unsymmetrical Nitrobiquinones
  作者：Min Yu、Helena C. Malinakova、Kenneth W. Stagliano

  DOI：10.1021/jo060825c

  日期：2006.8.1

  Novel 2-hydroxy-3-nitro-1,4-naphthoquinones were synthesized by an improved method utilizing nitronium tetrafluoroborate in high yields. A subsequent conversion to 2-chloro-3-nitro-1,4-naphthoquinones and a substitution of the chlorine by hydroxyquinone anions yielded 3-nitro-2,2‘-binaphthoquinones with a complete regiocontrol.

  利用改进的方法，利用四氟硼酸硝基鎓高产率地合成了新型的2-羟基-3-硝基-1,4-萘醌。随后转化为2-氯-3-硝基-1,4-萘醌并用羟基醌阴离子取代氯，得到具有完全区域控制的3-硝基-2,2'-联萘醌。
• Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone
  作者：Kenneth W. Stagliano、Ashkan Emadi、Zhenhai Lu、Helena C. Malinakova、Barry Twenter、Min Yu、Louis E. Holland、Amanda M. Rom、John S. Harwood、Ronak Amin、Allison A. Johnson、Yves Pommier

  DOI：10.1016/j.bmc.2006.04.034

  日期：2006.8

  Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase. Published by Elsevier Ltd.
• 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。
• 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