[3-(3,4,5-trimethoxyphenyl)oxiran-2-yl]phenylmethanone | 750604-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-(3,4,5-trimethoxyphenyl)oxiran-2-yl]phenylmethanone
• 英文别名: Phenyl[3-(3,4,5-trimethoxyphenyl)oxiran-2-yl]methanone；phenyl-[3-(3,4,5-trimethoxyphenyl)oxiran-2-yl]methanone
• CAS: 750604-73-0
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: UMOUAQVZPNWHEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-萘甲醚 、 [3-(3,4,5-trimethoxyphenyl)oxiran-2-yl]phenylmethanone 在 tris-(4-bromophenyl)aminium hexachloroantimonate 、 氧气 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium nitrite 作用下， 以 氯仿 为溶剂， 以63%的产率得到phenyl(1-(3,4,5-trimethoxyphenyl)naphtho[2,1-b]furan-2-yl)methanone
  参考文献：
  名称：

  查尔酮环氧化合物与2-萘醚之间的串联反应以构建复杂的萘并[2,1- b ]呋喃

  摘要：

  查尔酮环氧化物与2-萘醚的反应可以通过稳定的三芳基ami盐引发。然后在一个锅中进行好氧氧化芳构化后，输送了一系列多取代的萘​​并[2,1- b ]呋喃。

  DOI：

  10.1016/j.tetlet.2012.12.078
• 作为产物：
  描述：

  3,4,5-trimethoxychalcone 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以90%的产率得到[3-(3,4,5-trimethoxyphenyl)oxiran-2-yl]phenylmethanone
  参考文献：
  名称：

  Electrochemically Induced Ring-Opening/Friedel–Crafts Arylation of Chalcone Epoxides Catalyzed by a Triarylimidazole Redox Mediator

  摘要：

  The indirect anodic oxidation of chalcone epoxides in the presence of electron-rich heteroarenes mediated by a triarylimidazole (Med) was investigated by cyclic voltammetry (CV) and controlled potential electrolysis. The CV results indicate that a homogeneous electron transfer between Med(center dot+) and chalcone epoxides is facilitated by an electron-rich heteroarene that serves as an arylation reagent. The preparative scale electrolysis generated epoxide-ring-opened/Friedel-Crafts arylation products in moderate to good yields. The fact that only a catalytic amount of charge was required suggests that Med(center dot+) initiates a chain reaction. In addition, overoxidation of the products is avoided even though their oxidation potential is less than that of the starting chalcone epoxides.

  DOI：

  10.1021/jo5022184

文献信息

• Polymeric Ionic Liquid and Carbon Black Composite as a Reusable Supporting Electrolyte: Modification of the Electrode Surface
  作者：Seung Joon Yoo、Long-Ji Li、Cheng-Chu Zeng、R. Daniel Little

  DOI：10.1002/anie.201410207

  日期：2015.3.16

  of a supporting electrolyte to ensure the passage of charge. Frequently this causes separation and waste problems. To address these issues, a polymeric ionic liquid–Super P carbon black composite has been formulated. The system enables electrolyses to be performed without adding an additional supporting electrolyte, and its efficient recovery and reuse. In addition, the ability of the composite to modify

  使用电有机合成的主要障碍之一是需要大量的支持电解质以确保电荷通过。通常，这会导致分离和浪费问题。为了解决这些问题，已配制了一种聚合物离子液体-Super P炭黑复合材料。该系统无需添加额外的支持电解质即可进行电解，并实现了有效的回收和再利用。另外，复合材料原位修饰电极表面的能力导致改善的动力学。一个实际的结果是，可以在不牺牲效率的情况下降低催化剂的负载量。
• Friedel–Crafts alkylation between chalcone epoxides and heteroarenes induced by triarylaminium salt
  作者：Congde Huo、Xiaolan Xu、Xiaodong Jia、Xicun Wang、Jinzhu An、Chougu Sun

  DOI：10.1016/j.tet.2011.10.062

  日期：2012.1

  Triarylaminium salt was disclosed as a highly efficient nonmetallic initiator for the Friedel–Crafts reaction between chalcone epoxides and heteroarenes to construct a series of complex β-heteroaryl α-ketols in mild conditions and with good yields. Chalcone epoxides were presented as valuable halogen-free pre-electrophile in Friedel–Crafts alkylation through the formation of the stabilized benzylic

  三芳基ami盐是一种高效的非金属引发剂，可用于查尔酮环氧化物与杂芳烃之间的Friedel-Crafts反应，在温和条件下以高收率构建一系列复杂的β-杂芳基α-酮醇。查尔酮环氧化合物通过形成稳定的苄基阳离子中间体，在弗瑞德-克拉夫茨（Friedel-Crafts）烷基化反应中作为有价值的不含卤素的亲电子试剂出现。还提出了一个合理的自由基阳离子链机理。
• Approach to Construct Polysubstituted 1,2-Dihydronaphtho[2,1-<i>b</i>]furans and Their Aerobic Oxidative Aromatization
  作者：Congde Huo、Xiaolan Xu、Jinzhu An、Xiaodong Jia、Xicun Wang、Cheng Wang

  DOI：10.1021/jo300827s

  日期：2012.9.21

  2-naphthols to construct polysubstituted 1,2-dihydronaphtho[2,1-b]furans. The DDQ/NaNO2/O2 catalytic system was first applied to the aerobic oxidative aromatization of heterocycles, and a simple and efficient one-pot tandem FC alkylation/annulation/aerobic oxidative aromatization procedure was also developed for the synthesis of complex naphtho[2,1-b]furans.

  公开了三芳基ami盐作为查尔酮环氧化物和2-萘酚之间新型Friedel-Crafts烷基化/环状级联反应以构建多取代的1,2-二氢萘并[2,1- b ]呋喃的有效引发剂。DDQ / NaNO 2 / O 2催化系统首先用于杂环的好氧氧化芳构化，还开发了一种简单高效的一锅串联FC烷基化/环化/好氧氧化芳构化方法来合成复杂的萘[2]。 ，1- b ]呋喃。
• Tandem reaction between chalcone epoxides and 2-naphthyl ethers to construct complex naphtho[2,1-b]furans
  作者：Congde Huo、Jinzhu An、Xiaolan Xu、Xiaodong Jia、Xicun Wang、Lisheng Kang

  DOI：10.1016/j.tetlet.2012.12.078

  日期：2013.2

  The reaction of chalcone epoxides with 2-naphthyl ethers can be initiated by stable triarylaminium salt. And after subsequent aerobic oxidative aromatization in one pot, a series of polysubstituted naphtho[2,1-b]furans were delivered.

  查尔酮环氧化物与2-萘醚的反应可以通过稳定的三芳基ami盐引发。然后在一个锅中进行好氧氧化芳构化后，输送了一系列多取代的萘​​并[2,1- b ]呋喃。
• Electrochemically Induced Ring-Opening/Friedel–Crafts Arylation of Chalcone Epoxides Catalyzed by a Triarylimidazole Redox Mediator
  作者：Nan-ning Lu、Ni-tao Zhang、Cheng-Chu Zeng、Li-Ming Hu、Seung Joon Yoo、R. Daniel Little

  DOI：10.1021/jo5022184

  日期：2015.1.16

  The indirect anodic oxidation of chalcone epoxides in the presence of electron-rich heteroarenes mediated by a triarylimidazole (Med) was investigated by cyclic voltammetry (CV) and controlled potential electrolysis. The CV results indicate that a homogeneous electron transfer between Med(center dot+) and chalcone epoxides is facilitated by an electron-rich heteroarene that serves as an arylation reagent. The preparative scale electrolysis generated epoxide-ring-opened/Friedel-Crafts arylation products in moderate to good yields. The fact that only a catalytic amount of charge was required suggests that Med(center dot+) initiates a chain reaction. In addition, overoxidation of the products is avoided even though their oxidation potential is less than that of the starting chalcone epoxides.