6-propyl-2H-pyran-2-one | 5247-93-8

• 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-propyl-2H-pyran-2-one
• 英文别名: 2,4-octadien-5-olide；6-propyl-pyran-2-one；6-Propyl-α-pyron；6-propylpyran-2-one
• CAS: 5247-93-8
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: DIYWMJFAVIYCGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-氯吡喃-2H-酮 在 magnesium chloride hexahydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 mineral oil 为溶剂， 反应 2.5h， 生成 6-propyl-2H-pyran-2-one
  参考文献：
  名称：

  A flexible route to bioactive 6-alkyl-α-pyrones

  摘要：

  Both 6-chloro-alpha-pyrones and 3-chlorobenzopyran-l-ones react with malonates followed by a double decarboalkoxylation to give the corresponding alkyl and alkenyl products. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.01.063

文献信息

• 2<i>H</i>-Pyran-2-ones from<i>Trichoderma viride</i>and<i>Trichoderma asperellum</i>
  作者：Susanne M. Wickel、Christian A. Citron、Jeroen S. Dickschat

  DOI：10.1002/ejoc.201300049

  日期：2013.5

  Volatiles emitted by the soil fungi Trichoderma viride 272 and Trichoderma asperellum 328 were collected by using the closed loop stripping analysis (CLSA) headspace technique, and the obtained extracts were analysed by GC/MS. Several alkyl- and alkenyl-2H-pyran-2-ones, including known compounds 6-pentyl-2H-pyran-2-one and (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and the new derivatives (E)-6-(pent-

  土壤真菌绿色木霉 272 和木霉 328 释放的挥发物通过使用闭环汽提分析 (CLSA) 顶空技术收集，并通过 GC/MS 分析获得的提取物。几种烷基-和链烯基-2H-吡喃-2-酮，包括已知化合物 6-pentyl-2H-pyran-2-one 和 (E)-6-(pent-1-en-1-yl)-2H-pyran -2-one，以及新的衍生物 (E)-6-(pent-2-en-1-yl)-2H-pyran-2-one、6-丙基-2H-pyran-2-one 和 6-发现了庚基-2H-吡喃-2-one。还检测到烯基衍生物 (E)-6-(hept-1-en-1-yl)-2H-pyran-2-one，之前通过 MS 分析从海洋贵腐菌中初步鉴定出来。所有链烯基吡喃酮均通过使用报道的 Stille 偶联合成，然后进行内酯化，而烷基化吡喃酮是通过报道的合成方法通过 5-烷基戊-2-烯-5-内酯的自由基溴
• Synthesis of 2-Pyrones from Renewable Resources
  作者：Oliver Reiser、Daniel Dobler、Michael Leitner、Peter Kreitmeier

  DOI：10.1055/a-2085-4089

  日期：2023.8

  An atom-economic reaction sequence on a multigram scale for synthesizing 2-pyrone was developed starting from furfuryl alcohol, a renewable resource made from bran or bagasse, utilizing a large-scale thermal rearrangement of cyclopentadienone epoxide as the key step. Additionally, 6-substituted 2-pyrone natural product derivatives are readily accessible by this approach.

  从糠醇（一种由麸皮或甘蔗渣制成的可再生资源）开始，利用环戊二烯酮环氧化物的大规模热重排作为关键步骤，开发了用于合成 2-吡喃酮的多克级原子经济反应序列。此外，通过这种方法很容易获得 6-取代的 2-吡喃酮天然产物衍生物。
• Phosphine-Catalyzed Synthesis of 6-Substituted 2-Pyrones:  Manifestation of <i>E</i>/<i>Z</i>-Isomerism in the Zwitterionic Intermediate
  作者：Xue-Feng Zhu、Arnaud-Pierre Schaffner、Ronald C. Li、Ohyun Kwon

  DOI：10.1021/ol050946j

  日期：2005.7.1

  We report a one-step phosphine-catalyzed annulation between aldehydes and ethyl allenoate to form 6-substituted 2-pyrones. The mechanistic rationale for this reaction requires explicit discussion of the EIZ-isomerism of the zwitterionic intermediate formed by the addition of a phosphine to the allenoate. Sterically demanding trialkylphosphines facilitate the shift of equilibrium toward the E-isomeric zwitterion and lead to the formation of 6-substituted 2-pyrones. Various aromatic as well as aliphatic aldehydes undergo the transformation in moderate to excellent yield.
• Ogawa, Yoshimitsu; Maruno, Masao; Wakamatsu, Takeshi, Heterocycles, 1995, vol. 41, # 11, p. 2587 - 2599
  作者：Ogawa, Yoshimitsu、Maruno, Masao、Wakamatsu, Takeshi

  DOI：——

  日期：——
• PITTET A. O.; KLAIBER E. M., J. AGR. AND FOOD CHEM. <JAFC-AU>, 1975, 23, NO 6, 1189-1195
  作者：PITTET A. O.、 KLAIBER E. M.

  DOI：——

  日期：——