4-hydroxy-6-methyl-3-propionyl-2H-pyran-2-one | 22073-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-6-methyl-3-propionyl-2H-pyran-2-one
• 英文别名: 4-hydroxy-6-methyl-3-propanoylpyran-2-one
• CAS: 22073-84-3
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: IBQXMRVEHHEJCW-UHFFFAOYSA-N

物化性质

• 熔点：
  93-94 °C(Solv: ethanol (64-17-5))
• 沸点：
  316.3±42.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-methyl-3-propionyl-2H-pyran-2-one 在 六甲基磷酰三胺 、 lithium hydroxide 、 四氯化钛 、 sodium hydride 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 88.75h， 生成
  参考文献：
  名称：

  Myxopyronin B analogs as inhibitors of RNA polymerase, synthesis and biological evaluation

  摘要：

  A series of myxopyronin B analogs has been prepared via a convergent synthetic route and were tested for in vitro inhibitory activity against DNA-dependent RNA polymerase and antibacterial activity against E. coli and S. aureus. The parent lead compound proved to be very sensitive to even small changes. Only the achiral desmethyl myxopyronin B (1a) provided enhanced potency. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.045
• 作为产物：
  描述：

  4-Hydroxy-6-methyl-3-[1-(phenyl-hydrazono)-propyl]-pyran-2-one 在 羟基甲苯磺酰碘苯 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到4-hydroxy-6-methyl-3-propionyl-2H-pyran-2-one
  参考文献：
  名称：

  Pundeer, Rashmi; Chaudhri, Vishwas; Kinger, Mayank, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 5, p. 834 - 837

  摘要：

  DOI：

文献信息

• Antibacterial agents: high-potency myxopyronin derivatives
  申请人：Ebright Richard H.

  公开号：US09133155B2

  公开（公告）日：2015-09-15

  The invention provides compounds of Formula (I) and pharmaceutically acceptable salts thereof, wherein Ya, Yb, R1, R2, and G are as described in the specification, as well as compositions comprising a compound of formula (I). The compounds are useful as inhibitors of bacterial RNA polymerase and as antibacterial agents.

  该发明提供了化合物的公式(I)及其药用盐，其中Ya、Yb、R1、R2和G如规范中所述，以及包含公式(I)化合物的组合物。这些化合物可用作细菌RNA聚合酶的抑制剂和抗菌剂。
• Synthetic studies of fluorine-containing compounds for household insecticides
  作者：Tatsuya Mori、Kazuya Ujihara、Osamu Matsumoto、Kazunori Yanagi、Noritada Matsuo

  DOI：10.1016/j.jfluchem.2007.07.016

  日期：2007.10

  insecticides in our laboratory are described, i.e. amidoflumet, a new trifluoromethanesulfonanilide with high miticidal activity against various house dust mites, Metofluthrin, a potent new fluorinated pyrethroid with extremely high knockdown activity against various mosquitoes, and a new α-pyrone compound, 3-[1R-trans-(2-trifluoromethyl)cyclopropanecarbonyl]-4-hydroxy-6-methyl-2-pyrone with outstanding insecticidal

  描述了我们实验室中三种含氟杀虫剂的发现故事，即amidoflumet，一种对各种室内尘螨具有高杀螨活性的新型三氟甲烷磺酰苯胺，Metofluthrin，一种对各种蚊子具有极高击倒活性的强效新型氟化拟除虫菊酯，以及一种新的α吡喃酮化合物，3- [1 - [R -反式- （2-三氟甲基）环丙烷羰基] -4-羟基-6-甲基-2-吡喃酮与抗出色的杀虫活性德国小蠊。
• Substituted 2-pyrones, 2-pyridones, and other congeners of elasnin as potential agents for the treatment of chronic obstructive lung diseases
  作者：William C. Groutas、Michael A. Stanga、Michael J. Brubaker、Tien L. Huang、Min K. Moi、Robert T. Carroll

  DOI：10.1021/jm00146a023

  日期：1985.8

  Several congeners of elasnin (I) have been synthesized and shown to inhibit human leukocyte elastase (HLE). The C-3 alkyl substituted 2-pyrones 11 and 12 were found to be the most effective inhibitors of the enzyme. These compounds are highly specific in their inhibitory activity.

  已经合成了几种弹性蛋白（I）的同源物，并显示出它们抑制人白细胞弹性蛋白酶（HLE）。发现C-3烷基取代的2-吡喃酮11和12是该酶的最有效抑制剂。这些化合物在抑制活性方面具有高度特异性。
• Lithium Hydroxide Assisted <i>Endo</i> ‐Selective [4+4]‐Photocycloaddition of Pyran‐2‐ones
  作者：Lei Li、William L. Turnbull、Robert McDonald、F. G. West

  DOI：10.1002/ejoc.202100122

  日期：2021.4.26

  Readily accessible 3‐acyl‐4‐hydroxypyran‐2‐ones with pendent furans undergo [4+4]‐photocycloaddition reactions in the presence of lithium ion to afford lactone‐bridged cyclooctenones with complete selectivity for the endo cycloadducts.

  容易获得3-酰基-4- hydroxypyran -2-酮具有侧呋喃经历[4 + 4]在锂离子的存在下，得到内酯桥接cyclooctenones与用于完全选择性-photocycloaddition反应内切cycloadducts。
• Synthesis of new bi(pyrazolo[1,5-a]pyrimidinyl)-7-one derivatives from dehydroacetic acid and its analogues as antibacterial agents
  作者：Ranjana Aggarwal、Chinu Rani、Rajiv Kumar、Gaurav Garg、Jitender Sharma

  DOI：10.3998/ark.5550190.p008.089

  日期：——

  Synthesis of some new bi(pyrazolo[1,5-a]pyrimidinyl)-7-ones 3 was accomplished by the reaction of 3and/or 4-substituted 5-aminopyrazoles 2 with 3-acetyl-4-hydroxy-6-methyl2H-pyran-2-one (dehydroacetic acid, DHAA) 1a and its analogues 1b-c in refluxing ethanol. A tentative mechanism for the formation of 3 is proposed. These compounds were evaluated for their antibacterial activity against two Gram positive

  一些新的双(吡唑并[1,5-a]嘧啶基)-7-酮3的合成是通过3和/或4-取代的5-氨基吡唑2与3-乙酰基-4-羟基-6-甲基2H-反应完成的pyran-2-one（脱氢乙酸，DHAA）1a 及其类似物 1b-c 在回流乙醇中。提出了形成 3 的暂定机制。使用琼脂井评估了这些化合物对两种革兰氏阳性菌（即枯草芽孢杆菌 (MTCC 8509) 和嗜热脂肪芽孢杆菌 (MTCC 8505) 以及两种革兰氏阴性菌，即大肠杆菌（MTCC 119）和铜绿假单胞菌（MTCC 741））的抗菌活性扩散分析技术和最低抑菌浓度（MIC）方法。其中一种化合物 3d 显示出显着的抗菌活性。