2-methoxy-3,5-dimethyl-6-[(2E)-3-methylundecenyl]-4H-pyran-4-one | 544461-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-methoxy-3,5-dimethyl-6-[(2E)-3-methylundecenyl]-4H-pyran-4-one
• 英文别名: verticipyrone；2-methoxy-3,5-dimethyl-6-[(E)-3-methylundec-2-enyl]pyran-4-one
• CAS: 544461-53-2
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: INACFCTUORTUTR-FYWRMAATSA-N

物化性质

• 沸点：
  445.9±45.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-(1-methyl-2-oxopropyl)-2,2,5-trimethyl-4H-1,3-dioxin-4-one 在 吡啶 、 4-二甲氨基吡啶 、 disodium hydrogenphosphate 、 sodium amalgam 、 sodium methylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 正戊烷 为溶剂， 反应 5.0h， 生成 2-methoxy-3,5-dimethyl-6-[(2E)-3-methylundecenyl]-4H-pyran-4-one
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of Verticipyrone and Analogues

  摘要：

  Total synthesis of verticipyrone, a novel NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach using novel "Reverse Julia olefination" method. During total synthetic studies, we also prepared and evaluated several synthetic verticipyrone analogues, some of which exhibited more potent antiparasitic activity than the natural verticipyrone.

  DOI：

  10.1021/ol0626140

文献信息

• A Concise Route to α′-Methoxy-γ-pyrones and Verticipyrone Based Upon the Desymmetrization of α,α′-Dimethoxy-γ-pyrone
  作者：Michaël De Paolis、Helèna Rosso、Matthias Henrot、Cristina Prandi、Florent d'Herouville、Jacques Maddaluno

  DOI：10.1002/chem.201001780

  日期：——

  Two steps is the rule: A concise synthesis of versatile α′‐methoxy‐γ‐pyrones (see scheme) is described that uses an innovative desymmetrization of α,α′‐dimethoxy‐γ‐pyrone, relying upon conjugate addition of nucleophiles. This new strategy is applied to the preparation of α‐methyl‐ and α‐carboxaldehyde‐α′‐methoxy‐γ‐pyrones and to a short synthesis of verticipyrone.

  规则是两个步骤：描述了一种通用的α'-甲氧基-γ-吡喃酮的简明合成方法（参见方案），该方法利用创新的α，α'-二甲氧基-γ-吡喃酮的去对称性，依赖于亲核试剂的共轭加成。该新策略适用于制备α-甲基和α-甲醛，α'-甲氧基-γ-吡喃酮和维替吡酮的短合成。
• Carboalumination/Ni-catalyzed couplings. A short synthesis of verticipyrone
  作者：Bruce H. Lipshutz、Benjamin Amorelli

  DOI：10.1016/j.tetlet.2009.02.167

  日期：2009.5

  Verticipyrone (1) has been synthesized in six overall steps from commercially available ethyl-2-methylacetoacetate. This represents the first successful application of a modified Negishi carboalumination nickel-catalyzed cross-coupling reaction to a chloromethylated pyrone. (C) 2009 Elsevier Ltd. All rights reserved.
• Total Synthesis and Biological Evaluation of Verticipyrone and Analogues
  作者：Hiroyuki Shimamura、Toshiaki Sunazuka、Takashi Izuhara、Tomoyasu Hirose、Kazuro Shiomi、Satoshi Ōmura

  DOI：10.1021/ol0626140

  日期：2007.1.1

  Total synthesis of verticipyrone, a novel NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach using novel "Reverse Julia olefination" method. During total synthetic studies, we also prepared and evaluated several synthetic verticipyrone analogues, some of which exhibited more potent antiparasitic activity than the natural verticipyrone.