6-ethyl-4-methoxy-3-methyl-2H-pyran-2-one | 164531-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-ethyl-4-methoxy-3-methyl-2H-pyran-2-one
• 英文别名: 6-Ethyl-4-methoxy-3-methylpyran-2-one
• CAS: 164531-45-7
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: HNMQDFMUEKXHGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  6-ethyl-4-methoxy-3-methyl-2H-pyran-2-one 在 manganese(IV) oxide 、 selenium(IV) oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 环己烷 、 苯 为溶剂， 反应 72.5h， 生成 (E,E)-tert-butyl 5-(4-methoxy-3-methyl-2-oxo-2H-pyran-6-yl)-3-methylhexa-2,4-dienoate
  参考文献：
  名称：

  Total synthesis of infectopyrone, aplysiopsenes A–C, ent-aplysiopsene D, phomapyrones A and D, 8,9-dehydroxylarone, and nectriapyrone

  摘要：

  The total synthesis of the 2-pyrone natural products nectriapyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, and of 8,9-dehydroxylarone were achieved by Wittig olefination starting with vermopyrone. Infectopyrone was synthesized by Horner-Wadsworth-Emmons reaction starting with phomapyrone D. Racemic phomapyrone C methyl ether was obtained by hydrogenation of nectriapyrone. The total syntheses were achieved starting from commercially available 3,5-heptanedione and led to the desired natural products in 18-46% over 5-6 steps, whereupon all five-step syntheses were carried out with a single chromatographic workup. The total synthesis of infectopyrone, aplysiopsenes A-D, of phomapyrones A and D, and of 8,9-dehydroxylarone were achieved for the first time, giving unambiguous proof for the proposed structures of these natural products. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.104
• 作为产物：
  描述：

  sodium enolate of ethyl 2-methyl-3-oxobutanoate 在 正丁基锂 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 5.16h， 生成 6-ethyl-4-methoxy-3-methyl-2H-pyran-2-one
  参考文献：
  名称：

  吡喃酮的区域选择性功能化：通过 KHMDS 介导的羟醛缩合轻松合成 6-苯乙烯基吡喃酮

  摘要：

  在此，我们公开了我们致力于合成基于 kavalactone 的天然产物 penstyrypyrone 和其他相关的 4-OMe-2-pyrones，这些 4-OMe-2-pyrones 在 3-、5-和 7-位具有不同的取代基。此外，描述了一种通过KHMDS 介导的 2-吡喃酮的区域选择性羟醛缩合获得 6-苯乙烯基吡喃酮的简便方法，具有中等底物范围和良好到高产率（58-80%）。这种方法的效用通过去甲氧基仰光素、asnipyrone A 和 asnipyrone B 的立体选择性构建得到了例证。

  DOI：

  10.1016/j.tetlet.2021.153574

文献信息

• Convergent syntheses of luteoreticulin and didemethylluteoreticulin
  作者：John W. Lyga

  DOI：10.1002/jhet.5570320223

  日期：1995.3

  Convergent syntheses of luteoreticulin (1a) and didemethylluteoreticulin (1c) are described which are ammenable to structural variation in both the pyran and phenyl rings.

  描述了木犀草素（1a）和双二甲基木犀草素（1c）的收敛合成，它们可以在吡喃和苯环上进行结构变化。
• Total Synthesis of Gymnoconjugatins A and B
  作者：Robert S. Coleman、Matthew C. Walczak

  DOI：10.1021/jo061755c

  日期：2006.12.1

  Convergent and efficient syntheses of the microbial natural products gymnoconjugatin A and B are reported and were based on a linchpin coupling strategy using a boron/tin hetero-bis-metallated butadiene system.
• Total synthesis of infectopyrone, aplysiopsenes A–C, ent-aplysiopsene D, phomapyrones A and D, 8,9-dehydroxylarone, and nectriapyrone
  作者：Oliver Geiseler、Joachim Podlech

  DOI：10.1016/j.tet.2012.06.104

  日期：2012.9

  The total synthesis of the 2-pyrone natural products nectriapyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, and of 8,9-dehydroxylarone were achieved by Wittig olefination starting with vermopyrone. Infectopyrone was synthesized by Horner-Wadsworth-Emmons reaction starting with phomapyrone D. Racemic phomapyrone C methyl ether was obtained by hydrogenation of nectriapyrone. The total syntheses were achieved starting from commercially available 3,5-heptanedione and led to the desired natural products in 18-46% over 5-6 steps, whereupon all five-step syntheses were carried out with a single chromatographic workup. The total synthesis of infectopyrone, aplysiopsenes A-D, of phomapyrones A and D, and of 8,9-dehydroxylarone were achieved for the first time, giving unambiguous proof for the proposed structures of these natural products. (C) 2012 Elsevier Ltd. All rights reserved.
• Regioselective functionalization of pyrones: Facile synthesis of 6-styrylpyrones via KHMDS-mediated aldol condensation
  作者：Ramakrishna Samala、Manas K. Basu、K. Mukkanti

  DOI：10.1016/j.tetlet.2021.153574

  日期：2022.1

  Herein, we disclose our efforts directed toward the synthesis of the kavalactone-based natural product penstyrylpyrone and other related 4-OMe-2-pyrones possessing diverse substituents at the 3-, 5-, and 7-positions. Further, a facile approach to access 6-styrylpyrones via the KHMDS-mediated regioselective aldol condensation of 2-pyrones is described with moderate substrate scope and good to high yields

  在此，我们公开了我们致力于合成基于 kavalactone 的天然产物 penstyrypyrone 和其他相关的 4-OMe-2-pyrones，这些 4-OMe-2-pyrones 在 3-、5-和 7-位具有不同的取代基。此外，描述了一种通过KHMDS 介导的 2-吡喃酮的区域选择性羟醛缩合获得 6-苯乙烯基吡喃酮的简便方法，具有中等底物范围和良好到高产率（58-80%）。这种方法的效用通过去甲氧基仰光素、asnipyrone A 和 asnipyrone B 的立体选择性构建得到了例证。