1-(4-氯苯基)-2-(4-甲氧基苯基)乙烷-1,2-二酮 | 54945-17-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(4-氯苯基)-2-(4-甲氧基苯基)乙烷-1,2-二酮
• 英文名称: 1-(4-chlorophenyl)-2-(4-methoxyphenyl)ethane-1,2-dione
• CAS: 54945-17-4
• 化学式: C₁₅H₁₁ClO₃
• 分子量: 274.704
• InChiKey: UQWNRZSOZUMIIT-UHFFFAOYSA-N

物化性质

• 熔点：
  129.5 °C
• 沸点：
  437.0±30.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-2-(4-甲氧基苯基)乙烷-1,2-二酮 在 硫酸 、 sulfur 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.0h， 生成 2-(4-chlorophenyl)-3-(4-methoxyphenyl)pyrazine
  参考文献：
  名称：

  One-pot synthesis of unsymmetrical benzils and N-heteroarenes through nucleophilic aroylation catalyzed by N-heterocyclic carbene

  摘要：

  An efficient one-pot synthesis of various unsymmetrical benzils via N-heterocyclic carbene (NHC)-catalyzed aroylation of N-phenylimidoyl chlorides with aromatic aldehydes followed by acidic hydrolysis has been developed. The one-pot procedure was extended to synthesis of quinoxalines and pyrazines by condensation/annulation of unsymmetrical benzils generated in situ with diamines. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.039
• 作为产物：
  描述：

  1-(4-methoxyphenyl)-2-(4-chlorophenyl)acetylene 在 氧气 、 copper dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 14.0h， 以78%的产率得到1-(4-氯苯基)-2-(4-甲氧基苯基)乙烷-1,2-二酮
  参考文献：
  名称：

  铜-超氧在室温下可见光诱导的二芳基炔烃需氧氧化为α-二酮

  摘要：

  我们已经开发了在室温下可见光诱导的简单的铜（II）氯化铜催化分子氧将二芳基乙炔氧化为α-二酮的方法。该原位生成的铜（II）-superoxo配合物是一种吸光物质，可将惰性的二芳基乙炔氧化为α-二酮。与报道的光化学过程相反，当前的氧化方案不需要任何外源的光催化剂或自由基引发剂。绿色化学指标评估表明，当前氧化过程的E因子比报道的光化学过程的E因子高约2.3倍。当前反应在0-100的EcoScale上得分为63，表明合成过程适当。因此，整个氧化过程简单，对环境无害且在经济上可行。

  DOI：

  10.1039/d0gc00975j

文献信息

• Copper-Catalyzed Oxidation of Deoxybenzoins to Benzils under Aerobic Conditions
  作者：Antonella Goggiamani、Sandro Cacchi、Giancarlo Fabrizi、Antonia Iazzetti、Rosanna Verdiglione

  DOI：10.1055/s-0033-1338451

  日期：——

  Abstract A novel copper-catalyzed approach to benzils from readily available deoxybenzoins under neutral conditions using air as the oxidant has been developed. The reaction tolerates a variety of useful substituents including chloro, bromo, iodo, keto, ester, and cyano groups. A novel copper-catalyzed approach to benzils from readily available deoxybenzoins under neutral conditions using air as the

  摘要 已经开发出一种新颖的铜催化方法，该方法是在中性条件下使用空气作为氧化剂，从容易获得的脱氧安息香素制取苯甲醚。该反应可耐受多种有用的取代基，包括氯，溴，碘，酮，酯和氰基。 已经开发出一种新颖的铜催化方法，该方法是在中性条件下使用空气作为氧化剂，从容易获得的脱氧安息香素制取苯甲醚。该反应可耐受多种有用的取代基，包括氯，溴，碘，酮，酯和氰基。
• Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature
  作者：Vaibhav Pramod Charpe、Arunachalam Sagadevan、Kuo Chu Hwang

  DOI：10.1039/d0gc00975j

  日期：——

  the visible light induced simple copper(II) chloride catalyzed oxidation of diarylacetylenes to α-diketones by molecular oxygen at room temperature. The in situ generated copper(II)-superoxo complex is a light-absorbing species that oxidizes inert diarylacetylenes to α-diketones. In contrast to reported photochemical processes, the current oxidation protocol does not require any exogenous photocatalyst

  我们已经开发了在室温下可见光诱导的简单的铜（II）氯化铜催化分子氧将二芳基乙炔氧化为α-二酮的方法。该原位生成的铜（II）-superoxo配合物是一种吸光物质，可将惰性的二芳基乙炔氧化为α-二酮。与报道的光化学过程相反，当前的氧化方案不需要任何外源的光催化剂或自由基引发剂。绿色化学指标评估表明，当前氧化过程的E因子比报道的光化学过程的E因子高约2.3倍。当前反应在0-100的EcoScale上得分为63，表明合成过程适当。因此，整个氧化过程简单，对环境无害且在经济上可行。
• Dimethylzinc-mediated enantioselective addition of terminal alkynes to 1,2-diketones using perhydro-1,3-benzoxazines as ligands
  作者：Elena Prieto、Rebeca Infante、Javier Nieto、Celia Andrés

  DOI：10.1039/d1ob00249j

  日期：——

  dimethylzinc-mediated enantioselective monoaddition of aromatic and aliphatic terminal alkynes to 1,2-diketones. The corresponding α-hydroxyketones were obtained in good yields with high enantioselectivities starting from both aromatic and aliphatic 1,2-diketones. The alkynylation of unsymmetrical 1,2-diketones with electronically different substituents also proceeds with high regio- and enantioselectivity. This reaction

  衍生自 (-)-8-氨基薄荷醇的构象受限的全氢-1,3-苯并恶嗪在二甲基锌介导的芳香族和脂肪族末端炔烃与 1,2-二酮的对映选择性单加成反应中充当良好的手性配体。从芳香族和脂肪族 1,2-二酮开始，以高对映选择性获得相应的 α-羟基酮。具有不同电子取代基的不对称 1,2-二酮的炔基化也以高区域和对映选择性进行。该反应为合成带有手性叔炔丙醇的酮提供了一种实用的方法。
• Aryliminodimagnesium Reagents. VI. The Reactions with Conjugated Carbonyl Compounds. The Initial Coordination and the Electron-transfer in the Reactions of Organomagnesium Reagents
  作者：Masao Okubo、Masatoshi Yoshida、Kotomi Horinouchi、Hiroshi Nishida、Yoshinori Fukuyama

  DOI：10.1246/bcsj.56.1196

  日期：1983.4

  The reactions of aryliminodimagnesium reagents (ArN(MgBr)2) with benzylideneacetophenones, quinones, and benzils were examined. Among the product-distributions in the reactions with the enones and the α-diketones, some examples in which p-MeO-substituted substrates gave higher yields of condensation products were obtained. The results are in contrast with the product-distributions in the reaction of ArMgBr with Ar1COAr2 and that of ArN(MgBr)2 with Ar1NO2: p-Cl-Substituted substrates are advantageous for the formation of addition and/or condensation products. These reactions of the two organomagnesium reagents were classified into “coordination controlled” and “electron-transfer controlled” ones on the basis of the combination of electron-donating ability of reagents with the electron-accepting ability of substrates. The classification was illustrated also on the basis of the relative difference of the energy levels of HOMO’s and LUMO’s of the reactants.

  对芳基亚胺二溴化镁试剂（ArN(MgBr)2）与苄叉基乙酰苯、醌和苯基硫醇的反应进行了研究。在和烯酮及α-二酮反应产物的分布中，得到了一些实例，其中对甲氧基取代的底物给出了较高产率的缩合产物。这些结果与ArMgBr与Ar1COAr2以及ArN(MgBr)2与Ar1NO2反应产物的分布形成对比：对于加成和/或缩合产物的形成，对氯取代的底物具有优势。基于试剂的电子供体能力和底物的电子受体能力的结合，将这两种有机镁试剂的反应分类为“配位控制”和“电子转移控制”反应。这种分类也基于反应物HOMO和LUMO能级之间的相对差异进行了说明。
• Copper-mediated aerobic oxidative cleavage of α,β-unsaturated ketones to 1,2-diketones
  作者：Zheng Li、Junjun Yin、Gong Wen、Tianpeng Li、Xiaoli Shen

  DOI：10.1039/c4ra05307a

  日期：——

  The copper-mediated aerobic oxidative cleavage of α,β-unsaturated ketones to synthesize 1,2-diketones by using potassium acetate as a catalyst and sodium iodide as a promoter in acetic acid is described. The protocol has the advantages of using inexpensive and non-toxic raw materials, high yield and simple work-up procedure.

  描述了一种铜介导的有氧氧化裂解α,β-不饱和酮合成1,2-二酮的方法，该方法使用醋酸钾作为催化剂，碘化钠作为促进剂，在醋酸中进行。该方案的优点是使用便宜且无毒的原材料，产率高且操作步骤简单。