3-butyl-4-hydroxy-6-methyl-2-pyrone | 39849-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-butyl-4-hydroxy-6-methyl-2-pyrone
• 英文别名: 3-n-butyl-4-hydroxy-6-methyl-2-pyrone；3-butyl-4-hydroxy-6-methyl-pyran-2-one；3-butyl-4-hydroxy-6-methyl-2H-pyran-2-one；3-butyl-4-hydroxy-6-methylpyran-2-one
• CAS: 39849-74-6
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: KISDFPOOAUXVLU-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  290.7±40.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-butyl-4-hydroxy-6-methyl-2-pyrone 在 selenium(IV) oxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  A Synthetic Small Molecule F240B Decreases NLRP3 Inflammasome Activation by Autophagy Induction

  摘要：

  共轭聚烯烃是一类广泛存在的天然产物，具有各种生物功能。我们先前确定4-羟基奥克萨康胞素B（4-HAB）为一种抗炎剂，其IC₅₀约为20 µM。在这项研究中，我们合成了一种新的抗炎4-HAB类似物F240B，其IC₅₀小于1 µM。F240B剂量依赖性地通过增加自噬通量、LC3斑点形成和酸性囊泡器官形成诱导自噬。F240B通过诱导自噬抑制了NACHT、LRR和PYD结构域含蛋白3（NLRP3）炎症小体的激活。在一个机制研究中，F240B通过自噬抑制了白细胞介素（IL）-1β（IL-1β）前体的表达，促进了NLRP3和IL-1β的降解，并以自噬依赖的方式减少了线粒体膜完整性的丧失。此外，F240B抑制了与凋亡相关斑点样蛋白含有CARD（ASC）寡聚体化和斑点形成，而不影响NLRP3与ASC或NIMA相关激酶7（NEK7）和双链RNA依赖激酶（PKR）之间的相互作用。此外，F240B通过减少中性粒细胞的腹腔内流入和腹腔灌洗液中IL-1β、活性半胱氨酸蛋白酶-1、IL-6和单核细胞趋化蛋白-1（MCP-1）的水平，在尿酸晶体诱导的腹膜炎小鼠模型中表现出体内抗炎活性。总之，F240B通过诱导自噬减轻了NLRP3炎症小体的作用，并可能成为未来的抗炎剂。

  DOI：

  10.3389/fimmu.2020.607564
• 作为产物：
  描述：

  3-(2-buten-1-yl)-4-hydroxy-6-methyl-2-pyrone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以99%的产率得到3-butyl-4-hydroxy-6-methyl-2-pyrone
  参考文献：
  名称：

  Palladium-catalyzed C-alkylations of the highly acidic and enolic triacetic acid lactone. Mechanism and stereochemistry

  摘要：

  DOI：

  10.1021/jo00257a023

文献信息

• Copper and cobalt mediated regioselective alkylation of polyketide models: methyl 3,5-dioxohexanoate and triacetic acid lactone
  作者：Jordi Cervello、Jorge Marquet、Marcial Moreno-Mañas

  DOI：10.1016/s0040-4020(01)89770-2

  日期：1990.1

  Regioselective C-alkylations at the intercarbonyl positions C-4 and C-2 of the polyketide model methyl 3,5-dioxohexanoate, 1, have been acomplished through reactions of its cobalt(II), 4a, and copper(II), 4b, complexes respectively. Some examples of double alkylations at both positions are presented. Cyclizations of the regioselectively substituted diketoesters so prepared gave triacetic acid lactone

  通过其钴（II），4a和铜（II）4b的反应，完成了聚酮化合物模型3,5-二氧己酸甲酯1的羰基间位置C-4和C-2处的区域选择性C-烷基化，复杂。给出了两个位置上双烷基化的一些实例。如此制备的区域选择性取代的二酮酸酯的环化得到在C-5和C-3区域选择性烷基化的三乙酸内酯衍生物。
• Copper complex protection in the regioselective alkylation of methyl 3,5-dioxohexanoate. Preparation of 3-alkyl derivatives of 4-hydroxy-6-methyl-2-pyrone
  作者：Jordi Cervello、Jorge Marquet、Marcial Moreno-Mañas

  DOI：10.1016/s0040-4039(00)96365-2

  日期：1987.1

  Protection of the diketone moiety of the polyketide model methyl 3,5-dioxohexanoate by copper(II) complex formation followed by alkylation of the free C-2 position results in overall regioselective alkylation of the diketoester to afford methyl 2-alkyl-3,5-dioxohexanoates, which under cyclization afford 3-alkyl derivatives of triacetic acid lactone.

  通过铜（II）配合物的形成保护聚酮模型3,5-二氧己酸甲酯的二酮部分，然后将游离的C-2位置烷基化，将使二酮酸酯的整体区域选择性烷基化，从而得到2-烷基-3,5甲基-二氧己酸酯，在环化作用下得到三乙酸内酯的3-烷基衍生物。
• March, P. de; Moreno-Manas, M.; Pleixats, R., Heterocycles, 1984, vol. 21, # 2, p. 766
  作者：March, P. de、Moreno-Manas, M.、Pleixats, R.、Ripoll, I.

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of Polyenylpyrrole Derivatives as Anticancer Agents Acting through Caspases-Dependent Apoptosis
  作者：Zhanxiong Fang、Pei-Chun Liao、Yu-Liang Yang、Feng-Ling Yang、Yi-Lin Chen、Yulin Lam、Kuo-Feng Hua、Shih-Hsiung Wu

  DOI：10.1021/jm100619x

  日期：2010.11.25

  A class of polyenylpyrroles and their analogues were designed from a hit compound identified in a fungus. The compounds synthesized were evaluated for their cell cytotoxicity against human non-small-cell lung carcinoma cell lines A549. Two compounds were found to exhibit high cytotoxicity against A549 cells with IC50 of 0.6 and 0.01 mu M, respectively. The underlying mechanisms for the anticancer activity were demonstrated as caspases activation dependent apoptosis induction through loss of mitochondrial membrane potential, release of cytochrome c, increase in B-cell lymphoma-2-associated X protein (Bax) level, and decrease in B-cell lymphoma-2 (Bcl-2) level. The two compounds were nontoxic to normal human lung Beas-2b cells (IC50 > 80 mu M), indicating that they are highly selective in their cytotoxicity activities. Furthermore, one compound showed in vivo anticancer activity in human-lung-cancer-cell-bearing mice. These results open promising insights on how these conjugated polyenes mediate cytotoxicity and may provide a molecular rationale for future therapeutic interventions in carcinogenesis.
• A Method for the Alkylation at C-3 of 4-Hydroxy-6-methyl-2-pyrone (Triacetic Acid Lactone)
  作者：Marcial Moreno-Mañas、Roser Pleixats

  DOI：10.1055/s-1984-30864

  日期：——