ethyl 3-oxo-5-phenyl-4-pentenoate | 1503-99-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 3-oxo-5-phenyl-4-pentenoate
• 英文别名: ethyl (E)-3-oxo-5-phenylpent-4-enoate；ethyl cinnamoylacetate；ethyl 3-oxo-5-phenylpent-4-enoate；3-oxo-5-phenyl-4-pentenoic acid ethyl ester；Ethyl-3-oxo-5-phenylpent-4-enoate
• CAS: 1503-99-7
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: KNUYHVRRBLEIHT-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  ethyl 3-oxo-5-phenyl-4-pentenoate 在 乙醇 、 钯 作用下， 生成 3-氧代-5-苯基-戊酸乙酯
  参考文献：
  名称：

  Borsche; Lewinsohn, Chemische Berichte, 1933, vol. 66, p. 1792,1796

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 3-(phenylsulfonyl)but-3-enoate 在 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 25.0~50.0 ℃ 、600.0 MPa 条件下， 反应 84.0h， 生成 ethyl 3-oxo-5-phenyl-4-pentenoate
  参考文献：
  名称：

  Synthesis of the benzazepin-4-one ring system via dipolar cycloaddition of N-phenylnitrones with activated allenes

  摘要：

  DOI：

  10.1021/jo00265a018

文献信息

• Preparation of γ,δ-unsaturated-β-ketoesters: Lewis acid-catalysed C H insertion of ethyl diazoacetate into α,β-unsaturated aldehydes
  作者：Hirenkumar Gandhi、Timothy P. O'Sullivan

  DOI：10.1016/j.tetlet.2017.07.095

  日期：2017.9

  synthesis of γ,δ-unsaturated-β-keto esters was achieved by the Lewis acid-catalysed direct CH insertion of an α-diazoester into various α,β-substituted-unsaturated aldehydes. CH insertion of ethyl diazoacetate into alkyl- and aryl-substituted α,β-unsaturated aldehydes was performed under mild conditions to afford the corresponding γ,δ-unsaturated-β-keto esters in moderate to high yields as a mixture

  γ，δ-不饱和-β-酮酸酯的合成是通过路易斯酸催化的α-重氮酯直接C H插入各种α，β-取代的不饱和醛中来实现的。在温和的条件下将重氮基乙酸乙酯C H插入烷基和芳基取代的α，β-不饱和醛中，以中等至高收率的酮/烯醇混合物形式提供相应的γ，δ-不饱和-β-酮酸酯互变异构体。
• Ethyl 4-diphenylphosphinoyl-2-oxobutanoate: A convenient reagent for the synthesis of γ,δ-unsaturated β-ketoesters
  作者：J.A.M. van den Goorbergh、A. van der Gen

  DOI：10.1016/0040-4039(80)80252-8

  日期：1980.1

  Aldehydes and ketones can be converted into γ,δ-unsaturated-β-ketoesters by reaction with the dianion from phosphine oxide .

  通过与氧化膦中的二价阴离子反应，可以将醛类和酮类转化为γ，δ-不饱和-β-酮酸酯。
• Divergent Synthesis of Bicyclo[3.2.1]octenes and Cyclohexenes via Catalytic Annulations of Nazarov Reagent and Vinyl 1,2-Diketones
  作者：Wenjun Liu、Shengtong Niu、Zhifei Zhao、Shuang Yang、Jinggong Liu、Yongjin Li、Xinqiang Fang

  DOI：10.1021/acs.orglett.0c02763

  日期：2020.10.2

  are unique units that widely exist in natural products, but the rapid and stereoselective construction of this skeleton is a challenging issue. We report the stereodivergent synthesis of bicyclo[3.2.1]octenes using Nazarov reagents and alkenyl 1,2-diketones with Brønsted base catalysis under mild conditions. Both stereoisomers of the bridged products can be obtained by tuning the reaction conditions,

  双环[3.2.1]辛烷和相关结构是在天然产物中广泛存在的独特单元，但是该骨架的快速和立体选择性构造是一个具有挑战性的问题。我们报告在温和的条件下使用Nazarov试剂和烯基1,2-二酮与Brønsted碱催化的立体发散合成双环[3.2.1]辛烯。桥连产物的两种立体异构体可以通过调节反应条件来获得，并且环己烯产物也可以选择性地形成。
• Efficient Synthesis of Functionalized β-Keto Esters and β-Diketones through Regioselective Hydration of Alkynyl Esters and Alkynyl Ketones by Use of a Cationic NHC-Au^ICatalyst
  作者：Chandrahas Tarigopula、Ganesh Kumar Thota、Rengarajan Balamurugan

  DOI：10.1002/ejoc.201601025

  日期：2016.12

  Regioselective hydration of α-alkynyl esters and ketones by using a cationic NHC–AuI catalyst results in β-keto esters and β-diketones, respectively. Controlled release of water in acetone by aldol self-condensation under the reaction conditions makes acetone as better solvent than 1,4-dioxane/water for the hydration of α-alkynyl esters having sensitive ester moieties.

  通过使用阳离子 NHC-AuI 催化剂，α-炔基酯和酮的区域选择性水合分别产生 β-酮酯和 β-二酮。在反应条件下通过羟醛自缩合控制丙酮中水的释放使得丙酮成为比 1,4-二恶烷/水更好的溶剂，用于水合具有敏感酯部分的 α-炔基酯。
• Organocatalytic Asymmetric Formal [3+3] Cycloaddition Reactions of α,β-Unsaturated Aldehydes with Nazarov Reagents
  作者：Ming-Kui Zhu、Qiang Wei、Liu-Zhu Gong

  DOI：10.1002/adsc.200800174

  日期：2008.6.9

  An organocatalytic asymmetric formal [3+3] cycloaddition reaction of α,β-unsaturated aldehydes with Nazarov reagents promoted by prolinol derivatives afforded, after oxidation, 3,4-dihydropyranones in good yields with high enantioselectivities of up to 97% ee.

  α，β-不饱和醛与Nazarov试剂的有机催化不对称形式[3 + 3]环加成反应，由Prolinol衍生物促进，氧化后可提供高产率的3,4-二氢吡喃酮，对映选择性高达97％ee。