2,3-epoxy-3-(2-metoxyphenyl)-1-phenylpropan-1-one | 68235-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-epoxy-3-(2-metoxyphenyl)-1-phenylpropan-1-one
• 英文别名: 2-methoxychalcone epoxide；Methanone, [3-(2-methoxyphenyl)oxiranyl]phenyl-；[3-(2-methoxyphenyl)oxiran-2-yl]-phenylmethanone
• CAS: 68235-45-0
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: GDSJIKXMXQGWCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2,3-epoxy-3-(2-metoxyphenyl)-1-phenylpropan-1-one 在 三氟化硼乙醚 、 氢溴酸 、 乙二胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 6.08h， 生成 2-苯基-1-苯并呋喃
  参考文献：
  名称：

  由2-甲氧基查耳酮环氧化物构建2-芳基苯并[ b ]呋喃的有效方法

  摘要：

  已经报道了由2-甲氧基查耳酮环氧化物构造2-芳基苯并[ b ]呋喃的有效方法。2-甲氧基查尔酮环氧化物在2 mol％的BF 3 ·Et 2 O催化下进行Meerwein重排，然后在一锅中进行甲酰化反应，成功制得2-甲氧基脱氧安息香素。之后，通过2-甲氧基脱氧安息香与48％HBr的分子间环脱水，获得了高收率（87％–100％）的2-芳基苯并[ b ]呋喃。利用这种方法，可以方便地合成天然产物呋喃喃甲酸酯A和类花生四烯酸类化合物6的关键中间体。

  DOI：

  10.1016/j.tet.2013.12.050
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 6.0h， 生成 2,3-epoxy-3-(2-metoxyphenyl)-1-phenylpropan-1-one
  参考文献：
  名称：

  Biomimetic hydrogenation: a reusable NADH co-enzyme model for hydrogenation of α,β-epoxy ketones and 1,2-diketones

  摘要：

  A biomimetic method has been developed to transform alpha,beta-epoxy ketones or 1,2-diketones into corresponding beta-hydroxy ketones or alpha-hydroxy ketones using a catalytic amount of BNAH or BNA(+)Br(-). The regeneration of BNAH or BNA(+)Br(-) is achieved by a mixture of HCOOH/Et3N. A radical mechanism is proposed to explain these observations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.047

文献信息

• Practical Approach for Preparation of Unsymmetric Benzils from β-Ketoaldehydes
  作者：Libo Ruan、Min Shi、Nian Li、Xu Ding、Fan Yang、Jie Tang

  DOI：10.1021/ol403762e

  日期：2014.2.7

  An efficient and practical method for the synthesis of unsymmetric benzils from readily available β-ketoaldehydes has been developed. Various unsymmetric 1,2-diaryldiketones bearing functional groups have been obtained in good to excellent yields under mild reaction conditions. A plausible mechanism was proposed, and α,α-dichloroketone was considered as the key intermediate. The generation of α,α-dichloroketones

  已经开发了一种从容易获得的β-酮醛合成不对称苯的有效且实用的方法。在温和的反应条件下，已经获得了各种具有官能团的不对称的1,2-二芳基二酮，其收率很好。提出了一个合理的机制，并认为α，α-二氯酮是关键中间体。由β-酮醛生成α，α-二氯酮可经历以下步骤：（1）由次氯酸钠氧化，（2）脱羧，和（3）由次氯酸钠生成的Cl 2氯化。
• Solvent-Free Synthesis of 1,3-Diphenyl-5-arylpyrazole Derivatives
  作者：Ji-Tai Li、Ying Yin、Xian-Tao Meng

  DOI：10.2174/157017809788681383

  日期：2009.7.1

  The synthesis of 1,3-diphenyl-5-arylpyrazoles via the reactions of 2,3-epoxy-1-phenyl-3-aryl-1-propanones with phenylhydrazine was carried out in 48-84% yields at 230 °C under solvent-free condition within 1.5 h. This method provides several advantages such as operational simplicity, higher yield and solvent-free.

  该方法通过 2,3-环氧-1-苯基-3-芳基-1-丙酮与苯肼的反应合成 1,3-二苯基-5-芳基吡唑，在 230 °C 无溶剂条件下 1.5 小时内产率达到 48-84%。
• Efficient Synthesis of 5-Arylmethyl-5-phenylimidazolidine-2,4-dione (or 5-Arylmethyl-5-phenyl-2-thioxoimidazolidin-4-one) from Chalcone Oxides Under Ultrasound Irradiation
  作者：Ji-Tai Li、Xiao-Ya Xu、Ying Yin

  DOI：10.2174/157017811795038403

  日期：2011.3.1

  Synthesis of 5-arylmethyl-5-phenylimidazolidine-2,4-dione (or 5-arylmethyl-5-phenyl-2-thioxoimidazolidin-4- one) via the reaction of 3-aryl-2,3-epoxyl-1-phenyl-1-propanone and urea (or thiourea) was carried out in 57-98% yields at 50 °C in EtOH in the presence of KOH under ultrasound irradiation. The procedure has the advantages of mild conditions, short reaction time and high yield.

  通过 3-芳基-2,3-环氧基-1-苯基-1-丙酮与尿素（或硫脲）反应合成 5-芳基甲基-5-苯基咪唑烷-2,4-二酮（或 5-芳基甲基-5-苯基-2-硫酮咪唑烷-4-酮），在超声辐照下，于 50 °C，在 KOH 存在下，在 EtOH 中进行，收率为 57-98%。该方法具有条件温和、反应时间短和收率高等优点。
• Magnetic Nano-Fe₃O₄-Supported 1-Benzyl-1,4-dihydronicotinamide (BNAH): Synthesis and Application in the Catalytic Reduction of α,β-Epoxy Ketones
  作者：Hua-Jian Xu、Xin Wan、Yong-Ya Shen、Song Xu、Yi-Si Feng

  DOI：10.1021/ol203423u

  日期：2012.3.2

  A novel magnetically recoverable organic hydride compound was successfully constructed by using silica-coated magnetic nanoparticles as a support. An as-prepared magnetic organic hydride compound, BNAH (1-benzyl-1,4-dihydronicotinamide), showed efficient activity in the catalytic reduction of α,β-epoxy ketones. After reaction, the magnetic nanoparticle-supported BNAH can be separated by simple magnetic

  以二氧化硅包覆的磁性纳米粒子为载体，成功构建了新型的磁性可回收有机氢化物。制备的磁性有机氢化物化合物BNAH（1-苄基-1,4-二氢烟酰胺）在催化还原α，β-环氧酮中显示出有效的活性。反应后，可以通过简单的磁性分离来分离磁性纳米粒子负载的BNAH，这使得产物的分离更容易。
• PAA-supported Hantzsch 1,4-dihydropyridine ester: an efficient catalyst for the hydrogenation of α,β-epoxy ketones
  作者：Xin-Feng Zhou、Peng-Fei Wang、Ye Geng、Hua-Jian Xu

  DOI：10.1016/j.tetlet.2013.07.112

  日期：2013.9

  A new type of water-soluble polymer-supported NADH co-enzyme model-FAA (polyacrylic acid)-supported Hantzsch 1,4-dihydropyridine ester (PM-HEH) was designed and synthesized. Catalytic amount of the supported reagent was used in the hydrogenation of alpha,beta-epoxy ketones to the corresponding beta-hydroxy ketones and showed great catalytic efficiency in the reduction reaction. This PAA-HEH was an optimal potential for recycling use. (C) 2013 Elsevier Ltd. All rights reserved.