chromone epoxide | 76182-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: chromone epoxide
• 英文别名: 1a,7a-Dihydrooxireno[2,3-b]chromen-7-one
• CAS: 76182-73-5
• 化学式: C₉H₆O₃
• 分子量: 162.145
• InChiKey: LSLXLBOHPHORHF-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C(Solv: hexane (110-54-3))
• 沸点：
  326.9±42.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  chromone epoxide 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 3-hydroxychromen-4-one
  参考文献：
  名称：

  基于 PdII 预组织色酮受体的水中钆 III 的选择性荧光探针

  摘要：

  报道了基于色酮的荧光 Pd II复合物的合成、溶液研究、光化学性质和 X 射线结构。配体包含两个作为侧臂连接到乙二胺部分的色酮单元；在 Pd II络合物中，金属离子预组织了两个羟基色酮单元，形成了一个刚性结构，带有由四个氧原子形成的带负电荷的口袋，能够与硬金属阳离子（如离子）相互作用，从而产生稳定的双金属配合物。与 La III和 Gd III相互作用尤其是，423 nm 处的发射强度分别增加了 2 倍和 8 倍，而其他稀土离子则淬灭了荧光。对真实基质的荧光分光光度法研究表明，可以使用该系统作为选择性荧光探针来检测和追踪环境水中钆的存在，作为 OFF-ON 化学传感器，LOD 为 0.4 ppm，LOQ 为 1.2 ppm。

  DOI：

  10.1039/d1dt01753e
• 作为产物：
  描述：

  色酮 在 sodium hydroxide 、 双氧水 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以0.1 g的产率得到chromone epoxide
  参考文献：
  名称：

  色酮环氧化物的化学研究

  摘要：

  碱性过氧化氢将色酮和异黄酮（而不是黄酮）环氧化。3-取代的色酮环氧化物比其他化合物稳定得多。一种异黄酮环氧化物被转化为氟代醇，另一种转化为1,2-二醇。后者是2-羟基苯并二氢吡喃酮，并且通过2′-苯甲酰氧基-2，2-二溴苯乙酮的环化获得类似结构的化合物。色酮环氧化物的酸催化开环发生区域选择性产生3-羟基色氨酸。碱催化的开环也选择性地在3-位发生。酸和碱催化的2-甲基-异黄酮环氧化物的水解导致两个杂环的裂解，分别产生1,3-和1,2-二酮。该环氧化物与硫酸形成环状硫酸盐。

  DOI：

  10.1016/s0040-4020(01)83137-9

文献信息

• Facile epoxidation of α,β-unsaturated ketones with cyclohexylidenebishydroperoxide
  作者：Kavitha Jakka、Jinyun Liu、Cong-Gui Zhao

  DOI：10.1016/j.tetlet.2006.12.104

  日期：2007.2

  Cyclohexylidenebishydroperoxide was successfully used as the oxygen source for the oxidation of α,β-unsaturated ketones for the first time. The corresponding epoxides were obtained in excellent yields under the Weitz–Scheffer reaction conditions.

  环己叉基双氢过氧化物首次成功地用作氧化α，β-不饱和酮的氧源。在Weitz-Scheffer反应条件下，以优异的收率获得了相应的环氧化物。
• Reaction of 2-silylmethylcyclopropyl ketones with in situ oxirane-derived aldehydes and formation of 2-hydroxymethyl tetrahydrofurans
  作者：Veejendra K. Yadav、Archana Gupta

  DOI：10.1016/j.tetlet.2009.05.107

  日期：2009.8

  The enolates formed from Lewis acid treatment of (2-trimethylsilylmethyl)cyclopropyl alkyl and aryl ketones reacted with aldehydes formed in situ from alkoxy-, aryl- and vinyl-substituted oxiranes to generate aldol products in good yields. Selected aldol products were conveniently transformed into highly substituted tetrahydrofurans under oxidative conditions.

  由（2-三甲基甲硅烷基甲基）环丙基烷基和芳基酮的路易斯酸处理形成的烯醇化物与由烷氧基，芳基和乙烯基取代的环氧乙烷原位形成的醛反应，以高收率产生醛醇产物。在氧化条件下，将选定的羟醛产物方便地转化为高度取代的四氢呋喃。
• Epoxidation of chromones and flavonoids in ionic liquids
  作者：Roberta Bernini、Enrico Mincione、Antonietta Coratti、Giancarlo Fabrizi、Gianfranco Battistuzzi

  DOI：10.1016/j.tet.2003.11.032

  日期：2004.1

  A convenient and efficient procedure for the epoxidation of chromone, isoflavone, and chalcone derivatives using 1-butyl-3-methyl imidazolium tetrafluoroborate [bmim]BF4 as solvent and alkaline hydrogen peroxide as oxidant is described. All reactions proceed in good yields and faster than in conventional solvents. No evidence of formation of compounds derived from the opening of the epoxide ring was

  描述了使用1-丁基-3-甲基咪唑四氟硼酸酯[bmim] BF 4作为溶剂和碱性过氧化氢作为氧化剂对色酮，异黄酮和查尔酮衍生物进行环氧化的便捷有效方法。与常规溶剂相比，所有反应均以良好的收率和更快的速度进行。没有获得形成自环氧化物环的衍生化合物的证据。
• Efficient Synthesis of Ratiometric Fluorescent Nucleosides Featuring 3-Hydroxychromone Nucleobases
  作者：Marie Spadafora、Victoria Y. Postupalenko、Volodymyr V. Shvadchak、Andrey S. Klymchenko、Yves Mély、Alain Burger、Rachid Benhida

  DOI：10.1016/j.tet.2009.07.021

  日期：2009.9

  The synthesis of a novel class of fluorescent nucleosides featuring 2-aryl-3-hydroxychromones (3-HC) as base analogues is described. Nucleoside la bearing the 2-thienyl-3-HC nucleobase was prepared using sequential aryl-aldol condensation/cycloetherification or a Friedel-Crafts glycosylation as key steps. The synthesis of the triazolyl derivative 1b was achieved using a convergent 1,3-dipolar cycloaddition strategy. Fluorescence studies show that 3-HC-thienyl-nucleoside la displays high sensitivity of its dual emission to polarity changes and therefore is highly promising for nucleic acid labelling. (C) 2009 Elsevier Ltd. All rights reserved.
• Syntheses and Evaluation of 2- or 3-(<i>N</i>-Cyclicamino)chromone Derivatives as Monoamine Oxidase Inhibitors
  作者：Koichi Takao、Tsukasa Sakatsume、Hitoshi Kamauchi、Yoshiaki Sugita

  DOI：10.1248/cpb.c20-00579

  日期：2020.11.1

  A series of 2-(N-cyclicamino)chromone derivatives (1a-4c) and 3-(N-cyclicamino)chromone derivatives (5a-8c) were synthesized, and their monoamine oxidase (MAO) A and B inhibitory activities were studied as part of a structure-activity relationship investigation. Compounds 1a-4c showed no remarkable inhibition for MAO-A or MAO-B, whereas compounds 5a-8c (with a few exceptions) showed significant and selective inhibition of MAO-B. Of these compounds, 7c,7-methoxy-3-(4-phenyl-1-piperazinyl)-4H-1-benzopyran-4-one inhibited MAO-B the most potently and selectively, having IC50 of 15 nM and an MAO-B selectivity index of more than 6700; c.f, 50 nM and 2000, respectively, for safinamide. The mode of inhibition of 7c to MAO-B was competitive and reversible. Considering the IC50 values and selectivity indices of the other synthetic compounds, the presence of the methoxy group on the chromone ring (R-2) of 7c seemed to increase MAO-B inhibition. Molecular docking analysis also supports this hypothesis. Our results suggest that 3-(N-cyclicamino)chromones are useful lead compounds for the development of MAO-B inhibitors.