4-naphthalen-2-yl-2-oxo-but-3-enoic acid ethyl ester | 105074-51-9

• 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: 4-naphthalen-2-yl-2-oxo-but-3-enoic acid ethyl ester
• 英文别名: (E)-ethyl 4-(naphthalen-2-yl)-2-oxobut-3-enoate；(E)-ethyl 4-(naphthalen-3-yl)-2-oxobut-3-enoate；Ethyl 2-oxo-4-(2-naphthyl)-3-butenoate；ethyl (E)-4-naphthalen-2-yl-2-oxobut-3-enoate
• CAS: 105074-51-9
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: FWOJRIBIHANNQC-CSKARUKUSA-N

物化性质

• 熔点：
  105 °C(Solv: heptane (142-82-5))
• 沸点：
  416.5±28.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2-甲基喹啉 、 4-naphthalen-2-yl-2-oxo-but-3-enoic acid ethyl ester 以 水 为溶剂， 反应 0.2h， 以86%的产率得到(E)-ethyl 2-hydroxy-4-(naphthalen-2-yl)-2-(quinolin-2-ylmethyl)but-3-enoate
  参考文献：
  名称：

  Rao, Nalajala Nageswara; Mali, Prakash Rambhau; Meshram, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53B, # 9, p. 1153 - 1158

  摘要：

  DOI：
• 作为产物：
  描述：

  2-萘甲醛 在 盐酸 作用下， 以 乙酸酐 为溶剂， 反应 4.25h， 生成 4-naphthalen-2-yl-2-oxo-but-3-enoic acid ethyl ester
  参考文献：
  名称：

  Bris, Marie-Therese, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1275 - 1280

  摘要：

  DOI：

文献信息

• Iodine mediated a simple strategy for the synthesis of β,γ-unsaturated-α-ketoesters and its application for the synthesis of 4,5-dihydropyrazole derivatives
  作者：Anil Pommidi、Asha Begum Shaik、Anindita Chatterjee、Vijaya Laxmi Somarapu

  DOI：10.1007/s13738-020-01872-8

  日期：2020.7

  AbstractNovel and efficient method for the synthesis of a series of β,γ-unsaturated-α-ketoesters under mild conditions was developed. This one-step protocol was achieved by the reaction of electron-rich aromatic aldehydes and pyruvates in the presence of 10 mol% of molecular iodine in solvent-free condition at 80 °C temperature. A wide variety of substrates bearing electron releasing groups on aromatic

  摘要提出了在温和条件下合成一系列β，γ-不饱和α-酮酸酯的新方法。通过在80℃的温度下在无溶剂条件下，在10 mol％的分子碘存在下，富电子芳族醛与丙酮酸盐反应，可以实现这一一步操作。芳香族环上带有电子释放基团的多种底物具有良好的耐受性，并以中等至良好的产率提供了相应的β，γ-不饱和α-酮酸酯。这些β，γ-不饱和α-酮酸酯已被进一步用于合成4，5-二氢吡唑衍生物。 图形摘要
• Palladium-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Vinyl Cyclopropanes and β,γ-Unsaturated α-Keto Esters: An Effective Route to Highly Functionalized Cyclopentanes
  作者：Liang-yong Mei、Yin Wei、Qin Xu、Min Shi

  DOI：10.1021/om300896z

  日期：2012.11.12

  Palladium-catalyzed asymmetric formal [3+2] cycloaddition of vinyl cyclopropanes and β,γ-unsaturated α-keto esters proceeded smoothly in the presence of chiral imidazoline–phosphine ligands to give the corresponding highly functionalized cyclopentanes in good yields along with high diastereo- and enantioselectivities under mild conditions.

  在手性咪唑啉-膦配体的存在下，钯催化的乙烯基环丙烷和β，γ-不饱和α-酮酯的不对称形式[3 + 2]环加成反应顺利进行，从而得到相应的高度官能化的环戊烷，并具有较高的非对映体-收率。和温和条件下的对映选择性。
• Automated structure elucidation of two unexpected products in a reaction of anα,β-unsaturated pyruvate
  作者：Gary J. Sharman、Ian C. Jones、Mark P. Parnell、Michael C. Willis、Mary F. Mahon、Dean V. Carlson、Antony Williams、Mikhail Elyashberg、Kirill Blinov、Sergey G. Molodtsov

  DOI：10.1002/mrc.1396

  日期：2004.7

  The reaction between an α,β‐unsaturated pyruvate and ethyl diazoacetate (EDA) yielded two unexpected products. The structures of these products were determined by automated elucidation of the chemical structures using spectroscopic inputs of a series of 1D and 2D NMR data using the computer program ACD/Structure Elucidator, StrucEluc. The formation of these products is rationalised. Their structures

  α,β-不饱和丙酮酸和重氮乙酸乙酯 (EDA) 之间的反应产生了两种意想不到的产物。这些产品的结构是通过使用计算机程序 ACD/Structure Elucidator，StrucEluc，使用一系列 1D 和 2D NMR 数据的光谱输入自动解析化学结构来确定的。这些产品的形成是合理的。它们的结构也被 X 射线晶体学证实。版权所有 © 2004 John Wiley & Sons, Ltd.
• DABCO-catalyzed regioselective cyclization reactions of β,γ-unsaturated α-ketophosphonates or β,γ-unsaturated α-ketoesters with allenic esters
  作者：Cheng-Kui Pei、Lei Wu、Zhong Lian、Min Shi

  DOI：10.1039/c1ob06507f

  日期：——

  Highly efficient DABCO-catalyzed [4 + 2] cycloaddition of β,γ-unsaturated α-ketophosphonates or β,γ-unsaturated α-ketoesters with allenic esters gives the corresponding highly functionalized tetrahydropyran and dihydropyran derivatives in good to excellent yields and moderate to good regioselectivities under mild conditions.

  高效的DABCO催化的[4 + 2]与烯丙酸酯的β，γ-不饱和α-酮膦酸酯或β，γ-不饱和α-酮酸酯的环加成反应得到相应的高度官能化 四氢吡喃 和二氢吡喃衍生物，在温和条件下具有良好至优异的收率和中等至良好的区域选择性。
• Highly Enantioselective Intermolecular Stetter Reactions of β-Aryl Acceptors: α-Ketoester Moiety as Handle for Activation and Synthetic Manipulations
  作者：Eduardo Sánchez-Larios、Karen Thai、François Bilodeau、Michel Gravel

  DOI：10.1021/ol202040b

  日期：2011.9.16

  The use of beta,gamma-unsaturated-alpha-ketoesters in the intermolecular Stetter reaction furnishes 1,2,5-tricarbonyl compounds in high yield and excellent enantioselectivity. The alpha,delta-diketoesters generated using this methodology serve as useful synthetic building blocks via chemo- and diastereoselective transformations.