phomapyrone A | 144938-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: phomapyrone A
• 英文别名: Shjhziupbjkxfy-kzzdlznxsa-；4-methoxy-3-methyl-6-[(2E,4E)-4-methylhexa-2,4-dien-2-yl]pyran-2-one
• CAS: 144938-31-8
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: SHJHZIUPBJKXFY-KZZDLZNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  alkaline earth salt of/the/ methylsulfuric acid 在 [3-3H₃]propanoic acid 、 minimal essential medium 作用下， 反应 144.0h， 生成 phomapyrone A
  参考文献：
  名称：

  引起植物病原真菌的黑腿病菌 Phomapyrones：分离、结构测定、生物合成和生物活性

  摘要：

  从一组真菌病原体 Leptosphaeria maculans (Desm.) Ces 的分离物中分离出 phomapyrones DG、三个 2-pyrones 和一个香豆素并确定其结构。报道了无性阶段 Phoma lingam (Tode ex Fr.) Desm。此外，还首次从这些分离物中获得了 phomenin B、infectopyrone 和 polanrazines B 和 C。此外，基于 13C 标记的乙酸盐和丙二酸以及氘代甲硫氨酸的掺入结果，提出了用于 phomapyrones 生物合成的聚酮化合物途径。

  DOI：

  10.1016/j.phytochem.2004.10.011

文献信息

• 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.
• Phomapyrones from blackleg causing phytopathogenic fungi: isolation, structure determination, biosyntheses and biological activity
  作者：M CPEDRAS、P CHUMALA

  DOI：10.1016/j.phytochem.2004.10.011

  日期：2005.1

  The isolation and structure determination of phomapyrones D-G, three 2-pyrones and a coumarin, from a group of isolates of the fungal pathogen Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode ex Fr.) Desm, is reported. As well, phomenin B, infectopyrone, and polanrazines B and C were also obtained for the first time from these isolates. In addition, based on results

  从一组真菌病原体 Leptosphaeria maculans (Desm.) Ces 的分离物中分离出 phomapyrones DG、三个 2-pyrones 和一个香豆素并确定其结构。报道了无性阶段 Phoma lingam (Tode ex Fr.) Desm。此外，还首次从这些分离物中获得了 phomenin B、infectopyrone 和 polanrazines B 和 C。此外，基于 13C 标记的乙酸盐和丙二酸以及氘代甲硫氨酸的掺入结果，提出了用于 phomapyrones 生物合成的聚酮化合物途径。

表征谱图