6-(4-methoxyphenyl)dihydro-2H-pyran-2,4(3H)-dione | 133286-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(4-methoxyphenyl)dihydro-2H-pyran-2,4(3H)-dione
• 英文别名: 6-(4-Methoxyphenyl)oxane-2,4-dione
• CAS: 133286-42-7
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: YULYIIRCCHCLFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-methoxyphenyl)dihydro-2H-pyran-2,4(3H)-dione 在 乙醇 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 7.25h， 生成 (3E)-1-(1,3-dithiolan-2-ylidene)-4-(4-methoxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  A Novel Route to Alkenoyl- and Cinnamoylketene Dithioacetals

  摘要：

  2-乙酰基(乙氧羰基)亚甲基-1,3-二硫杂环戊烷和-二硫杂环己烷（1）与各种醛或酮缩合，以高产率得到相应的取代的2-(1-羧基-2-氧代-3-丁烯亚基)-1,3-二硫杂环戊烷和-二硫杂环己烷4，这些化合物在加热下顺利脱羧，以高产率得到标题化合物。

  DOI：

  10.1055/s-1991-26366
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 乙酰乙酸甲酯 生成 6-(4-methoxyphenyl)dihydro-2H-pyran-2,4(3H)-dione
  参考文献：
  名称：

  Ring Opening/Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols

  摘要：

  Ring-opening/C-C bond cleavage reactions induced by nucleophilic addition of methyl Grignard to 5,6-dihydro-2-pyrone (DHP) triflates 1 furnish homopropargyl alcohols (1 --> 2) stereospecifically with respect to the stereochemistry of 1. Carbonyl extrusion from DHP triflates provides a unified and operationally simple strategy for preparing chiral homopropargyl alcohols.

  DOI：

  10.1021/ja801018r

文献信息

• Annulation of 2<i>H</i>-Pyran onto 1-Oxa- or 1-Azacyclohexane-2,4-diones and Their Analogues via Sequential Condensation with α-Substituted Enals and 6π-Electrocyclization
  作者：Md. Imran Hossain、Elkhabiry Shaban、Taku Ikemi、Wei Peng、Hiroyuki Kawafuchi、Tsutomu Inokuchi

  DOI：10.1246/bcsj.20130069

  日期：2013.7.15

  2H-Pyrans are constructed on a 1-oxa- or 1-azacyclohexane-2,4-dione core via Knoevenagel condensation with enals followed by 6π-electrocyclization, which are readily catalyzed with ethylenediammonium diacetate. This formal [3 + 3] strategy constitutes C–O and C–C bond making and the diastereomer formation is circumvented using 6,6-disubstitution with the same aryl group in the 1-oxacyclohexane-2,4-diones. This facile methodology significantly advances the access to polysubstituted bicyclic 2H-pyrans with a versatile substrate choice and improved stability of the product.

  通过Knoevenagel缩合反应与烯醛反应，随后进行6π-电环化反应，以1-氧杂-或1-氮杂环己烷-2,4-二酮为核心构建了2H-吡喃衍生物，这些反应易于用乙二胺二乙酸盐催化。这种形式上的[3 + 3]策略构成了C–O和C–C键的形成，并通过在1-氧杂环己烷-2,4-二酮中使用相同的芳基进行6,6-二取代来避免立体异构体的形成。这种简便的方法学极大地促进了多取代双环2H-吡喃的合成，具有多样化的底物选择和产品稳定性的提高。
• ——
  作者：I. P. Lokot'、F. S. Pashkovskii、F. A. Lakhvich

  DOI：10.1023/a:1011913328785

  日期：——
• Synthesis and evaluation of the molluscicidal activity of the 5,6-dimethyl-dihydro-pyran-2,4-dione and 6-substituted analogous
  作者：Laura Cristiane de Souza、Aldenir Feitosa dos Santos、Antônio Euzébio Goulart Sant'Ana、Dennis de Oliveira Imbroisi

  DOI：10.1016/j.bmc.2004.01.001

  日期：2004.3

  Five dihydro-piran-2,4-diones, including 5,6-dimethyl-dihydro-piran-2,4-dione one of the intermediates of the synthesis of caloverticilic acid, were synthesized and submitted to molluscicidal bioassay. The compound's yields varied from moderate to good (42%- 80%) and were achieved through the preparation of the dianion of ethyl acetoacetate, reaction with and aldehyde followed by hydrolysis of the ester (NaOH, H2O, 2 h, T.A.) and lactonization in acidic medium (HCl, 0degreesC). The 5,6-dimethyl-dihydro-piran-2,4-dione and three analogous dihydro-piran-2,4-diones 6-substituted,-phenyl, (4-methoxy-phenyl), and -propenyl, showed significant activities against the Biomphalaria glabrata egg masses, while the analogous 6-(3,4-dimethoxy-phenyl) was inactive as molluscicide. This activity is reported for the first time, extending the range of biological activities of this group. (C) 2004 Elsevier Ltd. All rights reserved.
• Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures
  作者：Md. Imran Hossain、Marta Świtalska、Wei Peng、Mariko Takashima、Ning Wang、Marcel Kaiser、Joanna Wietrzyk、Shingo Dan、Takao Yamori、Tsutomu Inokuchi

  DOI：10.1016/j.ejmech.2013.08.008

  日期：2013.11

  A novel series of 1,2,4-trioxanes were synthesized from 2H-pyrans via photooxidation, and their antiproliferative and growth factor inhibitory activity has been investigated across a variety of human cancer cell lines. Compounds 5k, 51, 5s, 7a and 7c exhibited the highest activity and selectivity against a human leukemia (MV4-11) cell line (IC50 = 0.5 mu M). Compound 5o showed the highest growth factor inhibitory activity against a melanoma (LOX-IMVI) cancer cell line (GI(50) = 1.0 mu M). A SAR study has confirmed the importance of the 1,2,4-trioxane unit as a pharmacophore for anticancer activity. The computer-assisted database analysis, COMPARE, has suggested that the compounds have unique mechanisms of actions that were different from those of known anticancer drugs. Some of the selected trioxanes were tested against the NF54 strain, albeit showing weak antiplasmodial activity. The molecular docking of trioxanes and hemin reveals that a short distance (130 angstrom) leads to their physical contact. The UV-vis spectroscopic analysis ensured the definite complexation between 1,2,4-trioxanes and hemin. The role of hemin-trioxane interaction in the hemin-induced oxidative damage has been studied using methylene blue as a substrate by UV-vis spectroscopy. (C) 2013 Elsevier Masson SAS. All rights reserved.
• A Novel Route to Alkenoyl- and Cinnamoylketene Dithioacetals
  作者：Eun Bok Choi、In Kwon Youn、Chwang Siek Pak

  DOI：10.1055/s-1991-26366

  日期：——

  2-Acetyl(ethoxycarbonyl)methylene-1,3-dithietane and -dithiane (1) were condensed with various aldehydes or ketones to afford high yields of the corresponding substituted 2-(1-carboxy-2-oxo-3-butenylidene)-1,3-dithietanes and -dithianes 4, which upon heating decarboxylated smoothly to give the title compounds in high yield.

  2-乙酰基(乙氧羰基)亚甲基-1,3-二硫杂环戊烷和-二硫杂环己烷（1）与各种醛或酮缩合，以高产率得到相应的取代的2-(1-羧基-2-氧代-3-丁烯亚基)-1,3-二硫杂环戊烷和-二硫杂环己烷4，这些化合物在加热下顺利脱羧，以高产率得到标题化合物。