ethoxycarbonylmethyl acetoacetate | 57582-45-3

• 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: ethoxycarbonylmethyl acetoacetate
• 英文别名: Butanoic acid, 3-oxo-, 2-ethoxy-2-oxoethyl ester；(2-ethoxy-2-oxoethyl) 3-oxobutanoate
• CAS: 57582-45-3
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: GTLFVPOTMIMVCW-UHFFFAOYSA-N

物化性质

• 沸点：
  263.6±15.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethoxycarbonylmethyl acetoacetate 在 ammonium hydroxide 、 Novozym 435 、 potassium carbonate 作用下， 以 phosphate buffer 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 23.0h， 生成 ethoxycarbonylmethyl methoxycarbonylmethyl 1,4-dihydro-2,6-dimethyl-4-(3'-pyridyl)pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Candida antarctica lipase-catalyzed hydrolysis of 4-substituted bis(ethoxycarbonylmethyl) 1,4-dihydropyridine-3,5-dicarboxylates as the key step in the synthesis of optically active dihydropyridines

  摘要：

  Prochiral bis(ethoxycarbonylmethyl) substituted 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates were hydrolyzed enantioselectively by Candida antarctica lipase B (Novozym 435). The enantiomeric excesses varied from 68 to 93%, depending on the substituent at position 4. In some cases, the e.e. could be significantly increased by changing the solvent system. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00441-9
• 作为产物：
  描述：

  双乙烯酮 、 乙醇酸乙酯 在 potassium acetate 作用下， 生成 ethoxycarbonylmethyl acetoacetate
  参考文献：
  名称：

  Rectal absorption of lysozyme and heparin in rabbits in the presence of non-surfactant adjuvants.

  摘要：

  苯丙氨酸和苯甘氨酸的乙酰乙酰乙酸烯胺能促进兔子对溶菌酶和肝素等大分子药物的直肠吸收。1，3-二乙酰乙酸甘油酯、1，2-异亚丙基甘油-3-乙酰乙酸酯和乙酰乙酰乙酸乙酯也能促进溶菌酶和肝素的直肠吸收。溶菌酶是碱性化合物，肝素是酸性化合物，因此本研究中使用的非表面活性佐剂可以促进大分子化合物的直肠吸收，而不受其电化学性质的影响。同时加入钙离子会抑制佐剂的作用，因此佐剂与钙离子可能会形成络合物，从而降低这些化合物作为佐剂的功效。

  DOI：

  10.1248/cpb.32.2020

文献信息

• New 1,4-dihydropyridine derivatives with potent and long-lasting hypotensive effect.
  作者：KANJI MEGURO、MASAHIRO AIZAWA、TAKASHI SOHDA、YUTAKA KAWAMATSU、AKINOBU NAGAOKA

  DOI：10.1248/cpb.33.3787

  日期：——

  In a search for new 1, 4-dihydropyridine derivatives with a long-lasting effect on the cardiovascular system, a series of piperazinylalkyl esters (I) bearing a lipophilic substituent on the 4-nitrogen of the piperazine ring was synthesized and tested for hypotensive effect in spontaneously hypertensive rats (SHR). Compounds I, especially those having a diphenylmethyl moiety on the piperazine ring, showed extremely potent and long-lasting hypotensive properties. Analogues related to I were also prepared, and the structure-activity relationships are discussed.

  在寻找对心血管系统具有长效作用的新的1,4-二氢吡啶衍生物时，合成并测试了一系列在哌嗪环的4-氮上带有亲脂性取代基的吡哆酯类化合物I对自发性高血压大鼠(SHR)的降压效果。化合物I，尤其是那些在哌嗪环上有二苯甲基部分的化合物，显示出极其强大且长效的降压特性。还制备了与I相关的类似物，并讨论了结构-活性关系。
• The Specificity and Broad Multitarget Properties of Ligands for the Free Fatty Acid Receptors FFA3/GPR41 and FFA2/GPR43 and the Related Hydroxycarboxylic Acid Receptor HCA2/GPR109A
  作者：Egils Bisenieks、Brigita Vigante、Ramona Petrovska、Baiba Turovska、Ruslan Muhamadejev、Vitalijs Soloduns、Astrida Velena、Karlis Pajuste、Luciano Saso、Janis Klovins、Gunars Duburs、Ilona Mandrika

  DOI：10.3390/ph14100987

  日期：——

  The paradigm of ligand-receptor interactions postulated as “one compound—one target” has been evolving; a multi-target, pleiotropic approach is now considered to be realistic. Novel series of 1,4,5,6,7,8-hexahydro-5-oxoquinolines, pyranopyrimidines and S-alkyl derivatives of pyranopyrimidines have been synthesized in order to characterise their pleiotropic, multitarget activity on the FFA3/GPR41, FFA2/GPR43, and HCA2/GPR109A receptors. Hexahydroquinoline derivatives have been known to exhibit characteristic activity as FFA3/GPR41 ligands, but during this study we observed their impact on FFA2/GPR43 and HCA2/GPR109A receptors as well as their electron-donating activity. Oxopyranopyrimidine and thioxopyranopyrimidine type compounds have been studied as ligands of the HCA2/GPR109A receptor; nevertheless, they exhibited equal or higher activity towards FFA3/GPR41 and FFA2/GPR43 receptors. S-Alkyl derivatives of pyranopyrimidines that have not yet been studied as ligands of GPCRs were more active towards HCA2/GPR109A and FFA3/GPR41 receptors than towards FFA2/GPR43. Representative compounds from each synthesized series were able to decrease the lipopolysaccharide-induced gene expression and secretion of proinflammatory cytokines (IL-6, TNF-α) and of a chemokine (MCP-1) in THP-1 macrophages, resembling the effect of HCA2/GPR109A ligand niacin and the endogenous ligand propionate. This study revealed groups of compounds possessing multitarget activity towards several receptors. The obtained data could be useful for further development of multitarget ligands.

  配体-受体相互作用范式被提出为“一个化合物-一个靶标”，正在演变；多靶点、多效应途径现在被认为是现实的。为了表征它们在FFA3/GPR41、FFA2/GPR43和HCA2/GPR109A受体上的多效应、多靶点活性，已经合成了新的1,4,5,6,7,8-六氢-5-氧喹啉、吡喃吡嘧啶和吡喃吡嘧啶的S-烷基衍生物系列。已知六氢喹啉衍生物表现出作为FFA3/GPR41配体的特征活性，但在这项研究中，我们观察到它们对FFA2/GPR43和HCA2/GPR109A受体的影响，以及它们的电子给体活性。氧代吡喃吡嘧啶和硫代吡喃吡嘧啶类化合物已被研究为HCA2/GPR109A受体的配体；然而，它们表现出对FFA3/GPR41和FFA2/GPR43受体相同或更高的活性。尚未作为GPCR配体研究的吡喃吡嘧啶的S-烷基衍生物对HCA2/GPR109A和FFA3/GPR41受体的活性比对FFA2/GPR43更高。每个合成系列的代表性化合物能够降低THP-1巨噬细胞中脂多糖诱导的炎症细胞因子（IL-6、TNF-α）和趋化因子（MCP-1）的基因表达和分泌，类似于HCA2/GPR109A配体烟酸和内源性配体丙酸的作用。这项研究揭示了一些具有多靶点活性的化合物群。获得的数据对于进一步开发多靶点配体可能是有用的。
• 1,1-DISUBSTITUTED ETHYLENE PROCESS
  申请人：OptMed, Inc.

  公开号：US20130197263A1

  公开（公告）日：2013-08-01

  New and improved processes for the production of 1,1-disubstituted ethylenes.

  生产1,1-二取代乙烯的新改进工艺。
• [EN] DERIVATIVES OF 1,4-DIHYDROPYRIDINE POSSESSING ANTIVIRAL EFFICACY<br/>[FR] DÉRIVÉS DE 1,4-DIHYDROPYRIDINE PRÉSENTANT UNE ACTION ANTIVIRALE EFFICACE
  申请人：GRINDEKS

  公开号：WO2012010276A1

  公开（公告）日：2012-01-26

  New 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid ester type compounds having general formula (I), wherein R is hydrogen or carboxylate-methyl ester, R1 is sodium carboxylate-methyl ester, R2 is methyl, ethyl or sodium carboxylate-methyl ester, possessing antiviral efficacy.

  具有一般式（I）的新2,6-二甲基-1,4-二氢吡啶-3,5-二羧酸酯类化合物，其中R为氢或羧酸甲酯，R1为钠羧酸甲酯，R2为甲基、乙基或钠羧酸甲酯，具有抗病毒功效。
• DERIVATIVES OF 1,4-DIHYDROPYRIDINE POSSESSING ANTIVIRAL EFFICACY
  申请人：Stonans Ilmars

  公开号：US20130131126A1

  公开（公告）日：2013-05-23

  2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid ester type compounds having general formula I wherein R is hydrogen or carboxylate-methyl ester, R 1 is sodium carboxylate-methyl ester R 2 is methyl, ethyl or sodium carboxyate-methyl ester possessing antiviral efficacy.

  具有一般式I的2,6-二甲基-1,4-二氢吡啶-3,5-二羧酸酯类化合物，其中R为氢或羧酸甲酯，R1为羧酸甲酯钠，R2为甲基、乙基或羧酸甲酯钠，具有抗病毒功效。