4-methoxy-3,6-dimethyl-2H-pyran-2-one | 34818-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-methoxy-3,6-dimethyl-2H-pyran-2-one
• 英文别名: 4-Methoxy-3,6-dimethylpyran-2-one
• CAS: 34818-18-3
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: YWHWJTHKPHHCKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  4-methoxy-3,6-dimethyl-2H-pyran-2-one 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以65%的产率得到4-methoxy-5-methyl-6-oxo-6H-pyran-2-carbaldehyde
  参考文献：
  名称：

  Total Synthesis of Gymnoconjugatins A and B

  摘要：

  Convergent and efficient syntheses of the microbial natural products gymnoconjugatin A and B are reported and were based on a linchpin coupling strategy using a boron/tin hetero-bis-metallated butadiene system.

  DOI：

  10.1021/jo061755c
• 作为产物：
  描述：

  3,6-二甲基-4-羟基-2-吡喃酮 生成 4-methoxy-3,6-dimethyl-2H-pyran-2-one
  参考文献：
  名称：

  J. Med. Chem. 2010, 53, 7967-7978

  摘要：

  DOI：

文献信息

• Synthesis of novel 5,6-dehydrokawain analogs as osteogenic inducers and their action mechanisms
  作者：Momochika Kumagai、Keisuke Nishikawa、Takashi Mishima、Izumi Yoshida、Masahiro Ide、Keiko Koizumi、Munetomo Nakamura、Yoshiki Morimoto

  DOI：10.1016/j.bmcl.2017.04.016

  日期：2017.6

  protein (BMP) and activation of p38 MAPK signaling pathways. Compounds 14 and 21 also inhibited RANKL-induced osteoclast differentiation of RAW264 cells. These results indicated that novel 5,6-dehydrokawain analogs not only increase osteogenic activity but also inhibit osteoclast differentiation, and could be potential lead compounds for the development of anti-osteoporosis agents.

  破骨细胞的骨吸收和成骨细胞的骨形成之间的不平衡会导致骨丢失和骨相关疾病。在之前对增加成骨活性的天然产品的搜索中，我们发现来自 Alpinia zerumbet 的 5,6-dehydrokawain (1) 可促进成骨细胞生成。在这项研究中，我们合成并评估了一系列 5,6-dehydrokawain 类似物。我们的构效关系表明，1 芳环的对位或间位烷基化促进了成骨活性。在我们合成的潜在类似物中，(E)-6-(4-Ethylstyryl)-4-methoxy-2H-pyran-2-one (14) 和 (E)-6-(4-Butylstyryl)-4-methoxy- 2H-pyran-2-one (21) 在 10µM 时均显着上调 Runx2 和 Osterix mRNA 表达。这些成骨活性可能由骨形态发生蛋白 (BMP) 和 p38 MAPK 信号通路的激活介导。化合物 14 和 21 还抑制
• Regioselective functionalization of pyrones: Facile synthesis of 6-styrylpyrones via KHMDS-mediated aldol condensation
  作者：Ramakrishna Samala、Manas K. Basu、K. Mukkanti

  DOI：10.1016/j.tetlet.2021.153574

  日期：2022.1

  Herein, we disclose our efforts directed toward the synthesis of the kavalactone-based natural product penstyrylpyrone and other related 4-OMe-2-pyrones possessing diverse substituents at the 3-, 5-, and 7-positions. Further, a facile approach to access 6-styrylpyrones via the KHMDS-mediated regioselective aldol condensation of 2-pyrones is described with moderate substrate scope and good to high yields

  在此，我们公开了我们致力于合成基于 kavalactone 的天然产物 penstyrypyrone 和其他相关的 4-OMe-2-pyrones，这些 4-OMe-2-pyrones 在 3-、5-和 7-位具有不同的取代基。此外，描述了一种通过KHMDS 介导的 2-吡喃酮的区域选择性羟醛缩合获得 6-苯乙烯基吡喃酮的简便方法，具有中等底物范围和良好到高产率（58-80%）。这种方法的效用通过去甲氧基仰光素、asnipyrone A 和 asnipyrone B 的立体选择性构建得到了例证。
• Isolation of a 2-Pyrone Compound as an Antioxidant from a Fungus and Its New Reaction Product with 1,1-Diphenyl-2-picrylhydrazyl Radical
  作者：Akira HIROTA、Aya NEMOTO、Yukiko TSUCHIYA、Hiroshi HOJO、Naoki ABE

  DOI：10.1271/bbb.63.418

  日期：1999.1

  The indophenol-reducing compound, 4-hydroxy-3,6-dimethyl-2H-pyrane-2-one (I), was isolated from the culture filtrate of an unidentified fungus. I also reacted with the DPPH radical to form a reaction product IV which was determined to be 1-[4-(3,4-dihydro-3,6-dimethyl-2,4-dioxo- 2H-pyran-3-yl)phenyl]-1-phenyl-2-picrylhydrazine. This is the first report describing the formation of an adduct of the DPPH

  从未鉴定的真菌的培养滤液中分离出还原吲哚酚的化合物4-羟基-3,6-二甲基-2H-吡喃-2-酮（I）。我还与DPPH基团反应形成反应产物IV，该产物IV被确定为1- [4-（3,4-二氢-3,6-二甲基-2,4-二氧代-2H-吡喃-3-基）苯基] -1-苯基-2-吡啶甲基肼。这是第一份描述DPPH自由基及其清除剂加合物形成的报告。
• 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.
• An improved aldol protocol for the preparation of 6-styrenylpyrones
  作者：George A. Kraus、Umayangani K. Wanninayake

  DOI：10.1016/j.tetlet.2015.11.021

  日期：2015.12

  An improved aldol protocol for the synthesis of 6-styrenylpyrones is reported. The first synthesis of PTP1B inhibitor 1 and 4 has been described. (C) 2015 Elsevier Ltd. All rights reserved.