4-hydroxy-6-methyl-3-((2E,4E)-5-phenylpenta-2,4-dienoyl)-2H-pyran-2-one | 76678-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxy-6-methyl-3-((2E,4E)-5-phenylpenta-2,4-dienoyl)-2H-pyran-2-one
• 英文别名: 4-hydroxy-6-methyl-3-[(2E,4E)-5-phenyl-2,4-pentadienoyl]-2H-pyran-2-one；4-hydroxy-6-methyl-3-[(2E,4E)-5-phenylpenta-2,4-dienoyl]pyran-2-one
• CAS: 76678-65-4
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: IYNSQXHOISQFEH-NXZHAISVSA-N

物化性质

• 沸点：
  447.3±45.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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-((2E,4E)-5-phenylpenta-2,4-dienoyl)-2H-pyran-2-one 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 以91%的产率得到2-methyl-6-(4-phenyl-1,3-butadienyl)-4H-4-pyranone
  参考文献：
  名称：

  通过[6-（（E）-2-芳基乙烯基] -4-H-吡喃-4-酮和-[[E] -2-芳基乙烯基] -4-H-吡喃-4-酮的光氧化环化反应合成苯并[f]铬n-1-酮和苯基-4H-铬n-4-酮的新颖高效方法6 ‐ [（（1E，3E）‐4‐苯基丁a‐1,3‐dien‐1‐yl] ‐4H‐吡喃‐4‐1

  摘要：

  据报道，微波辅助快速有效地将2吡喃酮转化为4吡喃酮。然后，对6-[（（E）-2-芳基乙烯基] -2-甲基-4 H-吡喃-4-酮和2-甲基-6-[（1 E，3 E）-4- ]进行新的光催化氧化环化描述了在催化量的CuAlO 2的存在下，用紫外线在苯基丁1，3，dien-1，1基] -4 H，吡喃-4-1 。我们获得了新的3-甲基-1 H-苯并[ f ]铬n-1-酮和2-甲基-5-苯基-4 H-铬n-4-酮，它们已通过光谱技术进行了充分表征。

  DOI：

  10.1002/jhet.1694
• 作为产物：
  描述：

  反式肉桂醛 、 去氢乙酸 在 哌啶 、 吡啶 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以92%的产率得到4-hydroxy-6-methyl-3-((2E,4E)-5-phenylpenta-2,4-dienoyl)-2H-pyran-2-one
  参考文献：
  名称：

  4-羟基-6-甲基-3-（5-苯基-2 E，4 E-戊二烯-1-酰基）-2 H-吡喃-2-酮：胺的合成与反应性

  摘要：

  报道了4-羟基-6-甲基-3-（5-苯基-2 E，4 E-戊二烯-1-基）-2 H-吡喃-2-酮2与亲核试剂的合成和反应性研究。2与肼衍生物的反应生成新的吡唑型化合物，而与邻苯二胺的反应生成1,5-苯并二氮杂ze。2与乙胺的反应表示2 H -pyran-2-one开环并形成了强共轭化合物3。

  DOI：

  10.1002/jhet.5570410417

文献信息

• β-ketoenole dyes: Synthesis and study as fluorescent sensors for protein amyloid aggregates
  作者：Vladyslava Kovalska、Svitlana Chernii、Mykhaylo Losytskyy、Yan Dovbii、Iryna Tretyakova、Rafal Czerwieniec、Victor Chernii、Sergiy Yarmoluk、Sergiy Volkov

  DOI：10.1016/j.dyepig.2016.04.053

  日期：2016.9

  structure of the alkylamino group, the dyes could increase their fluorescence intensity in the dozens of times in the presence of insulin fibrils. The compound with a 2-hydroxyethylamino substituent demonstrates the highest fluorescence response (up to 60 times) and good range of insulin fibril detection (1–50 μg/ml). In complexes with fibrils, the dyes possess fluorescence quantum yield values up to 15% and

  β-酮烯酮（2 E，5 Z，7 E，9 E）-2-（烷基氨基）-6-羟基-10-苯基癸基-2,5,7,9-四烯基-4-酮的序列合成了烷基氨基尾基的一部分，并作为潜在的探针用于检测蛋白质不溶性聚集体-淀粉样原纤维。根据烷基氨基的结构，在存在胰岛素原纤维的情况下，染料可以将其荧光强度提高数十倍。具有2-羟乙基氨基取代基的化合物显示出最高的荧光响应（高达60倍）和良好的胰岛素原纤维检测范围（1–50μg/ ml）。在与原纤维的复合物中，染料的荧光量子产率值高达15％，结合常数约为2×105  M -1。β-酮烯酮的激发和发射最大值分别位于407–427 nm和500–554 nm范围内。这些化合物在游离时发出微弱的荧光，并且对天然蛋白质胰岛素和牛血清白蛋白稍微敏感。因此，β-酮烯醛被认为是荧光检测蛋白质淀粉样蛋白聚集体的预期分子。
• Drug design based on pentaerythritol tetranitrate reductase: synthesis and antibacterial activity of Pogostone derivatives
  作者：Biao Wang、Wei Huang、Jin Zhou、Xue Tang、Yang Chen、Cheng Peng、Bo Han

  DOI：10.1039/c7ob01429e

  日期：——

  Pogostone with potent antibacterial activity, we performed molecular docking studies of Pogostone with PETNR and analyzed structure–activity relationships, which guided the structure design and the subsequent facile organocatalytic synthesis of Pogostone derivatives under mild reaction conditions. Several of the synthesized compounds showed antibacterial activity in vitro, including one compound (3h)

  我们以前的工作表明，Pogostone通过靶向季戊四醇四硝酸酯还原酶（PETNR）发挥抗菌作用。为了开发具有强抗菌活性的Pogostone衍生物，我们进行了PETGO与Pogostone的分子对接研究，并分析了结构与活性之间的关系，这指导了结构设计以及随后在温和的反应条件下轻松进行有机催化合成Pogostone衍生物的工作。几种合成的化合物在体外均显示出抗菌活性，其中一种化合物（3h）对耐甲氧西林的金黄色葡萄球菌非常有效。这些结果表明，在侧链上带有官能团的Pogostone衍生物可能是抗菌药物开发的良好线索。
• Solvation of acylium fragment ions in electrospray ionization quadrupole ion trap and Fourier transform ion cyclotron resonance mass spectrometry
  作者：Ziqiang Guan、Jerrold M. Liesch

  DOI：10.1002/jms.124

  日期：2001.3

  In electrospray ionization (ESI) quadrupole ion trap and Fourier transform ion cyclotron resonance mass spectrometry, certain fragment ions (e.g. acylium ions) generated either during the ion transportation process (in the source interface region) or in the ion trap are found to undergo ion–molecule reactions with ESI solvent molecules (water, acetonitrile and aliphatic alcohols) to form adduct species. These unexpected solvated fragment ions severely complicate the interpretation of mass spectrometic data. High-resolution accurate mass measurements are important in establishing the elemental compositions of these adduct species and preventing erroneous data interpretation. Copyright © 2001 John Wiley & Sons, Ltd.

  在电喷雾电离（ESI）四极离子阱和傅立叶变换离子回旋共振质谱中，发现某些在离子传输过程（源接口区域）或离子阱中产生的碎片离子（如酰离子）与ESI溶剂分子（水、乙腈和脂肪醇）发生离子-分子反应，形成加合物。这些意外的溶剂化碎片离子使质谱数据的解释变得异常复杂。高分辨率精确质量测量对于确定这些加合物的元素组成并防止错误的数据解释非常重要。版权 © 2001 John Wiley & Sons, Ltd.
• Takeuchi, Naoki; Tobinaga, Seisho, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3007 - 3012
  作者：Takeuchi, Naoki、Tobinaga, Seisho

  DOI：——

  日期：——
• Cytotoxic and antibacterial activities of the analogues of pogostone
  作者：Zheng-wei Tang、Cheng Peng、Min Dai、Bo Han

  DOI：10.1016/j.fitote.2015.08.003

  日期：2015.10

  Six new (A5-A6, A8-A11) and six known (A1-A4, A7, PO) et-pyrone compounds were synthesized with dehydroacetate and aldehydes in tetrahydrofuran at room temperature. And their structures were determined by H-1-NMR, C-13-NMR and mass spectroscopy. In the bioscreening experiments, ten compounds (A1-A5, PO, A7-A10) exhibited antibacterial activities against Staphylococcus aureus ATCC 25923 with minimum inhibitory concentration (MIC) values of 4-512 mg/L, and nine compounds (Al-AS, PO, A7-A8, A10) exhibited antibacterial activities against Methicillin-resistant S. aureus (MRSA) ATCC 43300 with MIC values of 4-256 mg/L. Moreover, compound A10 showed the highest antibacterial activity against S. aureus ATCC 25923 and MRSA with MIC values of 4 mg/L, while the MIC values of Amoxicillin were 8 mg/I. and >256 mg/L, respectively. Two compounds (A8 and PO) exhibited antibacterial activities against Escherichia coli ATCC 25922 with MIC values of 32-512 mg/L However, only one compound (A8) exhibited significant antibacterial activity against Pseudomonas aeruginosa CVCC 3360 with MIC value of 256 mg/L. Moreover, A10 exhibited significant inhibition of proliferation in the four cell lines MCF-10, A549, A2780 and MFC, and showed stronger inhibitive activity of these four selected cell lines than cisplatin in the cytotoxic assay. Thus, this study suggests that pogostone analogues, especially A10, represented a kind of promising antibacterial and antineoplastic agents. (C) 2015 Elsevier B.V. All rights reserved.