2.4-Dimethyl-3.5-dioxo-hexansaeureethylester | 50496-42-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2.4-Dimethyl-3.5-dioxo-hexansaeureethylester
• 英文别名: Ethyl 2,4-dimethyl-3,5-dioxohexanoate
• CAS: 50496-42-9
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: XMOJMXCIWLDVEL-UHFFFAOYSA-N

物化性质

• 沸点：
  263.9±15.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2.4-Dimethyl-3.5-dioxo-hexansaeureethylester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 calcium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 109.0h， 生成 2-(2-hydroxyundecyl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors

  摘要：

  Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase ( complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 structural analogues were prepared and analyzed for their effects on mitochondrial NADH oxidoreductase and NADH oxidase activities. Also measured were the abilities of several of the analogues to inhibit respiration as judged by a shift to glycolysis, and to inhibit the growth of several mammalian cell lines. The nature of the pyrone ring was shown to be important to potency of inhibition, as was the length and nature of substituents in the side chain of the analogues. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.070
• 作为产物：
  描述：

  丙酸乙酯 在 正丁基锂 、 potassium tert-butylate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 2.4-Dimethyl-3.5-dioxo-hexansaeureethylester
  参考文献：
  名称：

  Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors

  摘要：

  Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase ( complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 structural analogues were prepared and analyzed for their effects on mitochondrial NADH oxidoreductase and NADH oxidase activities. Also measured were the abilities of several of the analogues to inhibit respiration as judged by a shift to glycolysis, and to inhibit the growth of several mammalian cell lines. The nature of the pyrone ring was shown to be important to potency of inhibition, as was the length and nature of substituents in the side chain of the analogues. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.070

文献信息

• A convenient synthesis of alkylated 4-hydroxy-2-pyrones
  作者：Eiji Suzuki、Haruo Sekizaki、Shoji Inoue

  DOI：10.1039/c39730000568

  日期：——

  Various alkylated 4-hydroxy-2-pyrones were synthesized from the βδ-diketo-esters (11), (13), and (14), which were easily prepared from the γδ-acetylenic β-keto-esters(3), (4), and (7)via the corresponding enamino-β-keto-esters (8)–(10).

  各种烷基化的4-羟基-2-吡喃酮从合成的β δ二酮-酯（11），（13）和（14），它很容易从制备的γ δ炔属β酮酯（3） ，（4）和（7）经由相应的烯氨基-β-酮酸酯（8）–（10）。
• Carboalumination/Ni-catalyzed couplings. A short synthesis of verticipyrone
  作者：Bruce H. Lipshutz、Benjamin Amorelli

  DOI：10.1016/j.tetlet.2009.02.167

  日期：2009.5

  Verticipyrone (1) has been synthesized in six overall steps from commercially available ethyl-2-methylacetoacetate. This represents the first successful application of a modified Negishi carboalumination nickel-catalyzed cross-coupling reaction to a chloromethylated pyrone. (C) 2009 Elsevier Ltd. All rights reserved.
• SUZUKI E.; SEKIZAKI H.; INOUE S., J. CHEM. RES. SYNOP., 1977, NO 8, 200
  作者：SUZUKI E.、 SEKIZAKI H.、 INOUE S.

  DOI：——

  日期：——