2-(乙氧基亚甲基)-3-氧代-己酸乙酯 | 125500-84-7

• 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
• 中文名称: 2-(乙氧基亚甲基)-3-氧代-己酸乙酯
• 英文名称: ethyl 2-(ethoxymethylene)-3-oxohexanoate
• 英文别名: Ethyl 2-butyryl-3-ethoxyacrylate；ethyl 2-(ethoxymethylidene)-3-oxohexanoate
• CAS: 125500-84-7
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: LECIVGGFOMFFFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  140 °C
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  2-(乙氧基亚甲基)-3-氧代-己酸乙酯 在 三氯氧磷 作用下， 以 1,4-二氧六环 、 二苯醚 为溶剂， 反应 2.67h， 生成 1-[8-甲氧基-4-[(2-甲基苯基)氨基]喹啉-3-基]丁烷-1-酮
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-Substituted-4-(phenylamino)quinolines

  摘要：

  Previously, gastric (H+/K+)-ATPase inhibitors such as 2 have been prepared as analogues of 1a on the presumption that the 3-carbethoxy substituent plays a key role in establishing the orientation of the 4-arylamino group. In this paper we explore further the contribution made to activity by the quinoline 3-substituent. We show th bearing such a substituent, only a particular combination of properties provides high activity, both in as inhibitors of gastric acid secretion in vivo. The ability of the substituent to affect activity by restricting rotation about the C(quin)-N bond through a combination of both a pi-electron withdrawal and hydrogen bonding is supported by the current study. However, high activity is only achieved if the effect of this group on the quinoline pK(a) is kept to a minimum. 3-Acyl substituents provide an optimum combination of electronic properties. From this series, compound 17c (SK&F 96067) was shown to be a potent inhibitor of histamine-stimulated gastric acid secretion oral dosing in the Heidenhain pouch dog and was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00096a018
• 作为产物：
  描述：

  丁酰乙酸乙酯 、 原甲酸三乙酯 在 乙酸酐 作用下， 以37%的产率得到2-(乙氧基亚甲基)-3-氧代-己酸乙酯
  参考文献：
  名称：

  Novel 3,6,7-Substituted Pyrazolopyrimidines as Positive Allosteric Modulators for the Hydroxycarboxylic Acid Receptor 2 (GPR109A)

  摘要：

  A number of pyrazolopyrimidines were synthesized and tested for their positive allosteric modulation of the HCA(2) receptor (GPR109A). Compound 24, an efficacious and potent agonist and allosteric enhancer of nicotinic acid's action, was the basis for most other compounds. Interestingly, some of the compounds were found to increase the efficacy of the endogenous ligand 3-hydroxybutyrate and enhance its potency almost 10-fold. This suggests that the pyrazolopyrimidines may have therapeutic value when given alone.

  DOI：

  10.1021/jm300164q

文献信息

• 一类含氮稠环类化合物、制备方法和用途
  申请人：上海凌达生物医药有限公司

  公开号：CN113527299A

  公开（公告）日：2021-10-22

  本发明公开了一类含氮稠环类化合物、制备方法和用途，具体为一种如通式I所示的含氮稠环类化合物、或其药学上可接受的盐、或其对映异构体、非对映异构体、互变异构体、扭转异构体、溶剂化物、多晶型物或前药、其制备方法及在药学上的应用，其中各基团的定义如说明书中所述。
• 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。
• Synthesis of Oxazolidin-4-ones: Domino <i>O</i>-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation
  作者：Abderrahman El Bouakher、Ronan Le Goff、Jordan Tasserie、Jérôme Lhoste、Arnaud Martel、Sébastien Comesse

  DOI：10.1021/acs.orglett.6b00851

  日期：2016.5.20

  An original and rapid domino reaction for access to oxazolidin-4-ones is presented. Simply by heating α-bromoamido alcohol in the presence of KNaCO3 and water with readily prepared Michael acceptors, an unprecedented molecular rearrangement is generated. This new methodology enables the hitherto unreported synthesis of functionalized oxazolidin-4-ones. The process was proved to be compatible with a

  提出了一种原始的快速多米诺骨牌反应来获得恶唑烷丁-4-酮。只需在KNaCO 3和存在下的水与易于制备的Michael受体一起加热α-溴酰胺醇，即可产生前所未有的分子重排。这种新方法使功能性的恶唑烷丁-4-酮迄今未见报道。事实证明，该方法可与多种底物兼容，并具有很高的区域选择性。
• Substituted 7-amino-thienopyridine derivatives as gastric acid secretion
  申请人：SmithKline Beckman Intercredit B.V.

  公开号：US04935431A1

  公开（公告）日：1990-06-19

  Substituted 4-aminothienopyridine derivatives which are inhibitors of gastric acid secretion. A compound of the invention is 6-butyryl-7-(2-isopropylphenylamino)-thieno[3,2-b]pyridine.

  这段话的意思是：替代4-氨基噻吩吡啶衍生物是胃酸分泌的抑制剂。发明的化合物是6-丁酰基-7-(2-异丙基苯胺)-噻吩[3,2-b]吡啶。 简单来说，这是一种可以抑制胃酸分泌的化合物，具体的化学名称是6-butyryl-7-(2-isopropylphenylamino)-thieno[3,2-b]pyridine。
• Compounds substituted quinoline derivatives
  申请人：SmithKline Beecham Intercredit B.V.

  公开号：US05432182A1

  公开（公告）日：1995-07-11

  Substituted 4-aminoquinazoline derivatives which are inhibitors of gastric acid secretion. A compound of the invention are the salts of strong acids of 3-butyryl-4-(2-methylphenylamino)-8-(hydroxymethyl)quinoline.

  该文段的中文翻译如下：替代4-氨基喹唑啉衍生物，是胃酸分泌的抑制剂。该发明的化合物是3-丁酰基-4-(2-甲基苯胺基)-8-(羟甲基)喹啉的强酸盐。