ethyl 3-oxo-2-phenyl-3-(4'-tolyl)propanoate | 613667-48-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl 3-oxo-2-phenyl-3-(4'-tolyl)propanoate
• 英文别名: ethyl 3-oxo-2-phenyl-3-(p-tolyl)propanoate；ethyl 3-(4-methylphenyl)-3-oxo-2-phenylpropanoate
• CAS: 613667-48-4
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: LSEBLQLXQZSNIW-UHFFFAOYSA-N

物化性质

• 沸点：
  399.3±27.0 °C(predicted)
• 密度：
  1.121±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 3-hydroxy-3-(4-methylphenyl)-2-phenylpropanoate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以41%的产率得到ethyl 3-oxo-2-phenyl-3-(4'-tolyl)propanoate
  参考文献：
  名称：

  Base-free two-step synthesis of 1,3-diketones and β-ketoesters from α-diazocarbonyl compounds, trialkylboranes, and aromatic aldehydes

  摘要：

  我们描述了一种收敛的无基团两步合成方法，通过三组分反应从α-二氮碳酰化合物、三烷基硼烷和芳香醛合成1,3-二酮和β-酮酯。这一合成方法的潜力在于能够在三步反应中合成多种对称的1,3,5-三芳基-4-烷基和1,3,4,5-四芳基取代的吡唑。

  DOI：

  10.1039/c1ob05150d

文献信息

• Palladium(II)-Catalyzed Desulfitative Synthesis of Aryl Ketones from Sodium Arylsulfinates and Nitriles: Scope, Limitations, and Mechanistic Studies
  作者：Bobo Skillinghaug、Christian Sköld、Jonas Rydfjord、Fredrik Svensson、Malte Behrends、Jonas Sävmarker、Per J. R. Sjöberg、Mats Larhed

  DOI：10.1021/jo501875n

  日期：2014.12.19

  The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The

  已经开发了一种快速有效的方案，在受控的微波辐射下，钯（II）催化从芳基亚磺酸钠和各种有机腈生产芳基酮。通过结合14个芳基亚磺酸钠和21个腈给出55个芳基酮实例，证明了该反应的广泛范围。另一个实例说明，通过选择腈反应物，苯并呋喃也是可得到的。通过电喷雾电离质谱和DFT计算研究了反应机理。还比较了从腈的脱硫合成芳基酮与从苯甲酸开始的相应转化。能量分布图的比较表明，2的脱羧所需的自由能 6-二甲氧基苯甲酸，尤其是苯甲酸比用于生成关键的芳基钯中间体的相应的脱硫方法要高。通过ESI-MS和DFT计算检测到的钯（II）中间体对催化循环提供了详细的了解。
• Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate
  作者：Mizzanoor Rahaman、M. Shahnawaz Ali、Khorshada Jahan、Damon Hinz、Jawad Bin Belayet、Ryan Majinski、M. Mahmun Hossain

  DOI：10.1021/acs.joc.0c02972

  日期：2021.5.7

  The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Brønsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl–methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl

  描述了在布朗斯台德酸催化剂存在下羰基化合物与重氮乙酸乙酯的反应的综合研究。结果，通过1，2-芳基/烷基/氢化物的转变，由多种酮和脂族醛合成了范围广泛的3-氧代酯。芳基甲基酮仅产生芳基迁移的产物，而其他酮则产生产物的混合物。对于二芳基酮，通过二维NMR光谱法证实了两种不可分离的迁移产物的身份。
• Enantioselective Synthesis of <i>syn</i>-α-Aryl-β-hydroxy Weinreb Amides: Catalytic Asymmetric Roskamp Reaction of α-Aryl Diazo Weinreb Amides
  作者：Sung Ho Shin、Eun Hee Baek、Geum-Sook Hwang、Do Hyun Ryu

  DOI：10.1021/acs.orglett.5b02268

  日期：2015.10.2

  highly optically active syn-α-aryl-β-hydroxy Weinreb amides using an asymmetric Roskamp/reduction strategy is described. An oxazaborolidinium ion catalyzed asymmetric Roskamp reaction of α-aryl diazo Weinreb amides with aldehydes produced α-phenyl-β-keto Weinreb amides, which were in situ reduced with zinc borohydride to give syn-α-aryl-β-hydroxy Weinreb amides in good yields (up to 87%) with high enantioselectivities

  描述了一种使用不对称Roskamp /还原策略合成各种高度旋光性的顺式-α-芳基-β-羟基Weinreb酰胺的便捷一锅法。恶唑硼烷鎓鎓离子催化α-芳基重氮Weinreb酰胺与醛的不对称Roskamp反应生成的α-苯基-β-酮基Weinreb酰胺，再用硼氢化锌将其还原，得到良好的合成-α-芳基-β-羟基Weinreb酰胺具有高对映体选择性（高达99％ee）和顺式立体选择性（> 20：1）的高收率（高达87％）。
• Palladium-catalyzed Cross-coupling of Aryl Iodides with β-Trimethylsiloxy-α-diazoesters: A Novel Approach toward β-Keto-α-arylesters
  作者：Zhibin Shu、Ji Zhang、Yan Zhang、Jianbo Wang

  DOI：10.1246/cl.2011.1009

  日期：2011.9.5

  Palladium-catalyzed cross-coupling of β-trimethylsiloxy-α-diazoesters with aryl iodides provides a new approach to β-keto-α-arylesters. It is shown that the β-trimethylsiloxy group can significantl...

  钯催化的β-三甲基甲硅烷氧基-α-重氮酯与芳基碘的交叉偶联为β-酮-α-芳基酯提供了一种新方法。结果表明，β-三甲基甲硅烷氧基能显着...
• [EN] NOVEL DIARYL PYRIMIDINONE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES DE DIARYLE PYRIMIDINEDIONE
  申请人：ORCHID CHEMICALS & PHARM LTD

  公开号：WO2003084935A2

  公开（公告）日：2003-10-16

  The present invention relates to novel diaryl pyrimidinedione derivatives of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their hydrates, their solvates, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. The present invention more particularly provides novel diaryl pyrimidinedione derivatives of the general formula (I).