ethyl 2-acetyl-3-ethoxybut-2-enoate | 99181-91-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 2-acetyl-3-ethoxybut-2-enoate
• CAS: 99181-91-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: HRRZQHSALUPAON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetyl-3-ethoxybut-2-enoate 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二苯醚 、 甲苯 为溶剂， 反应 4.0h， 生成 2-甲基-3-乙酰基-4-氯喹啉
  参考文献：
  名称：

  Structure−Activity Relationship of Quinoline Derivatives as Potent and Selective α_2C-Adrenoceptor Antagonists

  摘要：

  Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human alpha(2)-adrenoceptor subtypes (alpha(2A), alpha(2B), and alpha(2C.)). A number of compounds with good antagonist potencies against the alpha(2C)-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl) phenylamino] quinolin- 3- yl} methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the alpha(2C)-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the alpha(2C)-adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

  DOI：

  10.1021/jm060262x
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 1,1-二乙氧基乙烯 在 sodium ethanolate 作用下， 生成 ethyl 2-acetyl-3-ethoxybut-2-enoate
  参考文献：
  名称：

  Barnes; Kundiger; McElvain, Journal of the American Chemical Society, 1940, vol. 62, p. 1285

  摘要：

  DOI：

文献信息

• Polyketo-enols and chelates. Part I. The formation and constitution of xanthophanic enol and the xanthyrones
  作者：L. Crombie、D. E. Games、M. H. Knight

  DOI：10.1039/j39670000757

  日期：——

  A new structure is proposed, on the basis of spectroscopic and chemical evidence, for the yellow compound diethyl xanthophanic enol formed when ethyl sodioacetoacetate and ethyl ethoxymethyleneacetoacetate are heated together. A mechanism of formation is outlined and supported. The new information is used to prepare various compounds of the xanthyrone class and two of these, 3,3′,3′,5-tetra-acetyl

  根据光谱和化学证据，提出了一种新结构，该结构是将乙二乙酸乙酸乙酯和乙氧基亚甲基乙酰乙酸乙酯一起加热时形成的黄色化合物二乙基黄体烯醇。概述并支持了形成机制。新的信息可用于制备各种an吨酮类化合物，其中3,3'，3'，5-四乙酰基-6-丙烯基-α-吡喃酮和3'-乙酰基-3,3'中的两个5-三乙氧基羰基-6-丙烯基-α-吡喃酮使结构上的竞争者被打折。
• General and Rapid Pyrimidine Condensation by Addressing the Rate Limiting Aromatization
  作者：Daniel R. Fandrick、Delia Reinhardt、Jean-Nicolas Desrosiers、Sanjit Sanyal、Keith R. Fandrick、Shengli Ma、Nelu Grinberg、Heewon Lee、Jinhua J. Song、Chris H. Senanayake

  DOI：10.1021/ol500886a

  日期：2014.6.6

  and activated olefins was addressed to provide for a general and rapid process. A strong solvent effect was elucidated to affect the rate for the initial alkoxide elimination from the intermediate Michael adduct wherein polar aprotic solvents demonstrate an addition controlled aromatization. Spectroscopic studies support a solvent dependent equilibrium between the amidine and alkoxide base wherein the

  解决了在缩合方法中利用utilizing和活化的烯烃对嘧啶的限速芳构化，以提供一般和快速的方法。阐明了强溶剂作用以影响中间体迈克尔加合物中初始醇盐消除的速率，其中极性非质子溶剂表现出加成控制的芳构化。光谱研究支持the和醇盐碱之间的溶剂依赖性平衡，其中当强烈偏向toward阴离子的平衡时，芳构化速率最佳。
• Synthèse d'amino-5-pyrimidines et des sulfanilamids correspondants
  作者：R. Urban、O. Schnider

  DOI：10.1002/hlca.19580410635

  日期：——

  Durch Alkyl- und Alkoxy-Gruppen substituierte 5-Amino-pyrimidine wurden nach verschiedenen Methoden synthetisiert. Einige der daraus hergestellten Sulfanilamide zeichnen sich durch intensive und langdauernde chemotherapeutische Wirkung aus.

  通过各种方法合成被烷基和烷氧基取代的5-氨基嘧啶。由它们制得的一些磺酰苯胺具有强烈而持久的化学治疗作用。
• Toward Continuous‐Flow Synthesis of Biologically Interesting Pyrazole Derivatives
  作者：Amrita Das、Haruro Ishitani、Shū Kobayashi

  DOI：10.1002/adsc.201900954

  日期：2019.11.19

  continuous‐flow synthesis of substituted pyrazole derivatives has been developed via the formation of vinylidene keto esters as key intermediates. Heterogeneous Ni2+‐montmorillonite was found to be an efficient catalyst for orthoester condensation of 1,3‐dicarbonyls under flow conditions. The intermediate reacted with methylhydrazine to afford pyrazole derivatives, for which suitable selection of a solvent

  通过形成亚乙烯基酮基酯作为关键中间体，已开发出了一种两步连续流式合成取代吡唑衍生物的方法。发现非均相Ni2 +-蒙脱石是在流动条件下有效的1,3-二羰基原酸酯缩合催化剂。与甲基肼反应中间，得到吡唑衍生物，为此的溶剂的合适的选择在实现高产率和所需产物的优异的区域选择性发挥了关键作用。该协议的应用已通过合成生物活性吡唑的关键中间体（如Bixafen）得到了证明。
• Eine neue Pyrrolring-Synthese
  作者：C. A. Grob、K. Camenish

  DOI：10.1002/hlca.19530360109

  日期：——

  The Michael-type addition of 1-nitropropene to the N-substituted esters of β-aminocrotonic acid VIIIa and VIIIc leads directly to N-substituted 2,4-dimethyl-4-carbethoxy-pyrroles IVa and IVd in good yields.

  1-硝基丙烯在β-氨基巴豆酸VIIIa和VIIIc的N-取代的酯上的迈克尔型加成直接以良好的产率导致N-取代的2，4-二甲基-4-甲乙氧基-吡咯IVa和IVd。