6-[(E)-丁-2-烯-2-基]-4-甲氧基-3-甲基吡喃-2-酮 | 57685-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 6-[(E)-丁-2-烯-2-基]-4-甲氧基-3-甲基吡喃-2-酮
• 英文名称: 4-methoxy-3-methyl-6-[(1E)-1-methyl-1-propenyl]-2H-pyran-2-one
• 英文别名: (E)-6-(but-2-en-2-yl)-4-methoxy-3-methyl-2H-pyran-2-one；Nectriapyrone；4-Methoxy-3-methyl-6-(1-methyl-1-propenyl)-2-pyron；Nectriapyron；6-[(E)-but-2-en-2-yl]-4-methoxy-3-methylpyran-2-one
• CAS: 57685-79-7
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: NRLCQITWKJENAT-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 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

• 作为反应物：
  描述：

  6-[(E)-丁-2-烯-2-基]-4-甲氧基-3-甲基吡喃-2-酮 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以98%的产率得到6-but-2-yl-4-methoxy-3-methyl-2H-pyran-2-one
  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：

  2-Methyl-3-trimethylsiloxy-2-butensaeure-ethylester 在 N,N-二甲基丙烯基脲 、 正丁基锂 、 四氯化钛 、 potassium carbonate 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 10.67h， 生成 6-[(E)-丁-2-烯-2-基]-4-甲氧基-3-甲基吡喃-2-酮
  参考文献：
  名称：

  天然2-吡喃酮的合成与绝对构型

  摘要：

  合成4-羟基-2-吡喃酮的模块化方法可以在所有环位置引入烷基取代基，该方法被用于合成各种天然存在的2-吡喃酮，其中大多数是首次合成。对于手性化合物，对映选择性合成使我们能够确定天然产物的绝对构型。

  DOI：

  10.1002/ejoc.201800621

文献信息

• Induction of Nectriapyrone Biosynthesis in the Rice Blast Fungus <i>Pyricularia oryzae</i> by Disturbance of the Two-Component Signal Transduction System
  作者：Takayuki Motoyama、Toshihiko Nogawa、Toshiaki Hayashi、Hiroshi Hirota、Hiroyuki Osada

  DOI：10.1002/cbic.201800620

  日期：2019.3.1

  metabolism genes are poorly expressed under laboratory conditions. Nectriapyrones are known as secondary metabolites produced mainly by symbiotic fungi, including endophytes and plant pathogens. Herein, we show the induction of nectriapyrone production in the rice blast fungus Pyricularia oryzae. The two-component signal transduction system was disturbed by disrupting OSM1 and PoYPD1, which encoded a HOG

  大多数真菌次级代谢基因在实验室条件下表达不佳。Nectriapyrones被称为主要由共生真菌产生的次级代谢产物，包括内生菌和植物病原体。在本文中，我们显示了稻瘟病菌稻瘟病菌中产生吡喃酮的诱导。中断OSM1和PoYPD1干扰了两组分信号转导系统，后者分别编码HOG MAP激酶和含His的磷酸转移（HPt）蛋白。这诱导了两种聚酮化合物的产生：Nectriapyrone及其羟基类似物。Nectriapyrone生物合成基因簇由一个聚酮化合物合酶基因（NEC1）和一个O-甲基转移酶基因（NEC2）组成。这两个基因的过表达诱导了Nectriapyrone和5个Nectriapyrone类似物的过量生产，包括新的衍生产品。水稻感染不需要烟酰胺酮生产。Nectriapyrone的结构与链霉菌属菌种产生的杀菌素相似，Nectriapyrone抑制灰链霉菌的生长。
• 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.
• Synthesis and Absolute Configuration of Natural 2-Pyrones
  作者：Immo Burkhardt、Jeroen S. Dickschat

  DOI：10.1002/ejoc.201800621

  日期：2018.6.29

  in the synthesis of various naturally occurring 2‐pyrones, most of which were synthesized for the first time. For chiral compounds, an enantioselective synthesis allowed us to determine the absolute configurations of the natural products.

  合成4-羟基-2-吡喃酮的模块化方法可以在所有环位置引入烷基取代基，该方法被用于合成各种天然存在的2-吡喃酮，其中大多数是首次合成。对于手性化合物，对映选择性合成使我们能够确定天然产物的绝对构型。

表征谱图