4-羟基-6-(1-丙烯基)-吡喃-2-酮 | 21534-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4-羟基-6-(1-丙烯基)-吡喃-2-酮
• 英文名称: (E)-4-hydroxy-6-(prop-1-en-1-yl)-2H-pyran-2-one
• 英文别名: 4-hydroxy-6-[(E)-prop-1-enyl]pyran-2-one
• CAS: 21534-03-2
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: LAZYRSUGAIOZQO-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-羟基-6-(1-丙烯基)-吡喃-2-酮 在 碘苯二乙酸 、 三氟乙酸 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 3-epi-radicinin
  参考文献：
  名称：

  Synthesis of Deoxyradicinin, an Inhibitor of Xylella fastidiosa and Liberibacter crescens, a Culturable Surrogate for Candidatus Liberibacter asiaticus

  摘要：

  Pierce's disease of grapevine and citrus huanglongbing are caused by the bacterial pathogens Xylella fastidiosa and Candidatus Liberibacter asiaticus (CLas), respectively. Both pathogens reside within the plant vascular system, occluding water and nutrient transport, leading to a decrease in productivity and fruit marketability and ultimately death of their hosts. Field observations of apparently healthy plants in disease-affected vineyards and groves led to the hypothesis that natural products from endophytes may inhibit these bacterial pathogens. Previously, we showed that the natural product radicinin from Cochliobolus sp. inhibits X. fastidiosa. Herein we describe a chemical synthesis of deoxyradicinin and establish it as an inhibitor of both X. fastidiosa and Liberibacter crescens, a culturable surrogate for CLas. The key to this three-step route is a zinc-mediated enolate C-acylation, which allows for direct introduction of the propenyl side chain without extraneous redox manipulations.

  DOI：

  10.1021/acs.jnatprod.9b01207
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 在 正丁基锂 、 四氯化钛 、 戴斯-马丁氧化剂 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.5h， 生成 4-羟基-6-(1-丙烯基)-吡喃-2-酮
  参考文献：
  名称：

  Synthesis and Herbicidal Activity Against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin

  摘要：

  报告了一种新的合成策略，用于获得（±）-3-去氧根毒素（2）。这种合成方法比以前文献中报道的方法更高效，同时在C-7和C-2位置引入不同侧链的多功能性也更高。所得化合物（±）-2对草类杂草牛草具有植物毒性，与天然植物毒素根毒素（1）相当。因此，（±）-2可以作为比1更实用的合成替代品，用于牛草控制的生物除草剂。

  DOI：

  10.3390/molecules24173193

文献信息

• [EN] CITRUS HUANGLONGBING THERAPEUTIC COMPOUNDS<br/>[FR] COMPOSÉS THÉRAPEUTIQUES POUR LE HUANGLONGBING DES AGRUMES
  申请人：UNIV CALIFORNIA

  公开号：WO2021150951A1

  公开（公告）日：2021-07-29

  Certain embodiments of the invention provide a method of inhibiting Candidatus Liberibacter asiaticus (CLas) growth and/or treating a CLas infection (e.g., Huanglongbing) in a plant, comprising introducing to the plant at least one compound selected from the group consisting of: a cladosporol compound, a radicinin compound (e.g., a compound of formula (I)), and an epicoccamide compound, or a salt thereof. This present invention also provides methods of screening or identifying CLas inhibitory compounds.

  本发明的某些实施例提供了一种抑制亚洲型解脱假单胞菌（CLas）生长和/或治疗植物中CLas感染（例如黄龙病）的方法，包括向植物引入来自以下组合中至少一种化合物：一种克拉多斯孢醇化合物、一种雷地西宁化合物（例如，式（I）的化合物）和一种史高氏菌素化合物，或其盐。本发明还提供了筛选或识别CLas抑制化合物的方法。
• Synthesis of 6-Substituted 4-Hydroxy-2-pyrones from Aldehydes by Addition of an Acetoacetate Equivalent, Dess-Martin Oxidation and Subsequent Cyclization
  作者：Thorsten Bach、Stefan Kirsch

  DOI：10.1055/s-2001-18759

  日期：——

  A three step procedure for the synthesis of 6-substituted 4-hydroxy-2-pyrones 2 from aldehydes 1 is described. An acetoacetate equivalent 3 was added to the corresponding aldehyde (10 examples) in a vinylogous Mukaiyama aldol addition (72-99%). The intermediate alcohols 4 were oxidized to the ketones 5 using the Dess-Martin method (67%-quant.). A final thermal cyclization of compounds 5 yielded the title compounds 2 (61-92%; 40-85% overall).

  描述了一种从醛1合成6-取代的4-羟基-2-吡喃酮2的三步程序。向相应的醛中加入了一种乙酰乙酸酯等效物3（10个例子）进行维尼洛戈斯Mukaiyama aldol加成（72-99%）。中间醇4通过Dess-Martin方法被氧化为酮5（67%-量）。最后对化合物5进行热环化反应，得到了目标化合物2（61-92%；整体转换率为40-85%）。
• Production of Octaketide Polyenes by the Calicheamicin Polyketide Synthase CalE8: Implications for the Biosynthesis of Enediyne Core Structures
  作者：Katherine Belecki、Jason M. Crawford、Craig A. Townsend

  DOI：10.1021/ja904391r

  日期：2009.9.9

  Enediyne antibiotics are categorized according to the presence of either a 9- or 10-membered ring within their polyketide-derived core structures. Recent literature reports have favored the notion that biosynthetic divergence of the two structural families is determined by the enediyne polyketide synthases (PKSs) alone. We now disclose the simultaneous in vitro production of three octaketide polyenes by biosynthetic enzymes for the 10-membered enediyne calicheamicin Y-1(1), including the elusive beta-keto acid precursor to a previously described C15 methyl hexaenone. Alongside these two polyene products, we have additionally detected a hydrocarbon heptaene previously isolated only from 9-membered enediyne systems. The discovery of the heptaene in the calicheamicin system promotes a more convergent model for the early steps of enediyne biosynthesis. Furthermore, the synthesis of this set of octaketides by the enediyne PKS CalE8 and thioesterase CalE7 suggests, in contrast to recent biosynthetic proposals, that accessory enzymes may be necessary to initiate differentiation to 9- or 10-membered enediyne precursors,;1 either by modulation of enediyne PKS activity or by interception and modification of polyketide chain-extension intermediates.
• Synthesis of Deoxyradicinin, an Inhibitor of <i>Xylella fastidiosa</i> and <i>Liberibacter crescens</i>, a Culturable Surrogate for <i>Candidatus</i> Liberibacter asiaticus
  作者：Connor A. Brandenburg、Claudia A. Castro、Alex A. Blacutt、Elizabeth A. Costa、Kyler C. Brinton、Diana W. Corral、Christopher L. Drozd、M. Caroline Roper、Philippe E. Rolshausen、Katherine N. Maloney、Jonathan W. Lockner

  DOI：10.1021/acs.jnatprod.9b01207

  日期：2020.6.26

  Pierce's disease of grapevine and citrus huanglongbing are caused by the bacterial pathogens Xylella fastidiosa and Candidatus Liberibacter asiaticus (CLas), respectively. Both pathogens reside within the plant vascular system, occluding water and nutrient transport, leading to a decrease in productivity and fruit marketability and ultimately death of their hosts. Field observations of apparently healthy plants in disease-affected vineyards and groves led to the hypothesis that natural products from endophytes may inhibit these bacterial pathogens. Previously, we showed that the natural product radicinin from Cochliobolus sp. inhibits X. fastidiosa. Herein we describe a chemical synthesis of deoxyradicinin and establish it as an inhibitor of both X. fastidiosa and Liberibacter crescens, a culturable surrogate for CLas. The key to this three-step route is a zinc-mediated enolate C-acylation, which allows for direct introduction of the propenyl side chain without extraneous redox manipulations.
• Synthesis and Herbicidal Activity Against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin
  作者：Giulia Marsico、Maria Sabrina Ciccone、Marco Masi、Fabrizio Freda、Massimo Cristofaro、Antonio Evidente、Stefano Superchi、Patrizia Scafato

  DOI：10.3390/molecules24173193

  日期：——

  A novel synthetic strategy for obtainment of (±)-3-deoxyradicinin (2) is reported. This synthetic methodology is more efficient than those previously reported in the literature and also shows higher versatility towards the introduction of different side-chains at both C-7 and C-2. The obtained compound (±)-2 shows phytotoxicity against the grass-weed buffelgrass comparable to that of the natural phytotoxin radicinin (1). Therefore, (±)-2 can constitute a more practical synthetic alternative to 1 as bioherbicide for buffelgrass control.

  报告了一种新的合成策略，用于获得（±）-3-去氧根毒素（2）。这种合成方法比以前文献中报道的方法更高效，同时在C-7和C-2位置引入不同侧链的多功能性也更高。所得化合物（±）-2对草类杂草牛草具有植物毒性，与天然植物毒素根毒素（1）相当。因此，（±）-2可以作为比1更实用的合成替代品，用于牛草控制的生物除草剂。