ethyl 2,2-diacetoxypropionate | 1092954-34-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2,2-diacetoxypropionate
• 英文别名: Ethyl 2,2-diacetyloxypropanoate；ethyl 2,2-diacetyloxypropanoate
• CAS: 1092954-34-1
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: QYDNJPIGLXMHBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-diacetoxypropionate 在 phosphotungstic acid 、 溶剂黄146 作用下， 生成 ethyl 2-(acetoxy)acrylate
  参考文献：
  名称：

  An efficient heteropolyacid catalyzed acylation of pyruvate esters to α-acyloxyacrylate esters as potential candidate monomers for bio-based polymers

  摘要：

  在温和条件下，由丙酮酸酯和羧酸酐有效合成α-酰氧基丙烯酸酯。这些酯是具有高耐久性和透明度的生物基聚合物的潜在候选单体。钨基 Keggin 型杂多酸，尤其是 H3PW12O40，作为该反应的催化剂比其他典型酸更有效。

  DOI：

  10.1039/b809940e
• 作为产物：
  描述：

  丙酮酸乙酯 、 乙酸酐 在 phosphotungstic acid 作用下， 反应 3.0h， 以52%的产率得到ethyl 2,2-diacetoxypropionate
  参考文献：
  名称：

  An efficient heteropolyacid catalyzed acylation of pyruvate esters to α-acyloxyacrylate esters as potential candidate monomers for bio-based polymers

  摘要：

  在温和条件下，由丙酮酸酯和羧酸酐有效合成α-酰氧基丙烯酸酯。这些酯是具有高耐久性和透明度的生物基聚合物的潜在候选单体。钨基 Keggin 型杂多酸，尤其是 H3PW12O40，作为该反应的催化剂比其他典型酸更有效。

  DOI：

  10.1039/b809940e

文献信息

• An efficient synthesis of α-acyloxyacrylate esters as candidate monomers for bio-based polymers by heteropolyacid-catalyzed acylation of pyruvate esters
  作者：Wataru Ninomiya、Masahiro Sadakane、Shinji Matsuoka、Hiroki Nakamura、Hiroyuki Naitou、Wataru Ueda

  DOI：10.1039/b914515j

  日期：——

  A series of α-acyloxyacrylate esters are candidate monomers for bio-based polymers, converted from biomass feedstock. Polymers from these monomers are useful materials for bio-based plastics showing high heat resistance and transparency. In this paper, a new efficient method for α-acyloxyacrylate ester synthesis with a strong inorganic acid, heteropolyacid, is presented. The reaction in the presence of the heteropolyacid catalyst was carried out in liquid phase under mild conditions and showed higher productivity than that of the conventional synthesis with a typical organic acid, p-toluenesulfonic acid. Among the various heteropolyacids examined, α-Keggin-type tungsten-based phosphotungstic acid, H3PW12O40, showed the best performance, suggesting that the acid strength of the heteropolyacid is the crucial property for this reaction. We also found that pyruvate ester was consecutively converted into α-acyloxyacrylate estervia2,2-diacyloxypropionate ester.

  一系列α-酰氧基丙烯酸酯是生物基聚合物的候选单体，这些单体由生物质原料转化而来。由这些单体聚合得到的聚合物是具有高耐热性和透明度的生物基塑料的有用材料。本文提出了一种新的高效方法，使用强无机酸——杂多酸来合成α-酰氧基丙烯酸酯。在杂多酸催化剂存在下，反应在液相温和条件下进行，其生产效率高于使用典型有机酸——对甲苯磺酸的传统合成方法。在所考察的多种杂多酸中，α-Keggin型钨基磷钨酸H3PW12O40表现最佳，这表明杂多酸的酸强度是该反应的关键特性。我们还发现，丙酮酸酯连续转化为α-酰氧基丙烯酸酯，是通过2,2-二酰氧基丙酸酯途径进行的。
• Influence of structural differences and acidic properties of phosphotungstic acids on their catalytic performance for acylation of pyruvate ester to α-acyloxyacrylate ester
  作者：Wataru Ninomiya、Masahiro Sadakane、Yutaro Ichi、Toshiya Yasukawa、Ken Ooyachi、Tsuneji Sano、Wataru Ueda

  DOI：10.1016/j.cattod.2010.10.047

  日期：2011.4

  Dawson-type (H6P2W18O62) and Preyssler-type (H14[NaP5W30O110]) phosphotungstic acids, were examined as catalysts for acylation of ethyl pyruvate with acetic anhydride to synthesize ethyl α-acetoxyacrylate in liquid phase. This compound is one of candidate monomers for bio-based polymers bearing high thermal durability and transparency. Catalytic performances correlated to the acid strength, the proton number

  各种杂多酸，包括Keggin型（H 3 PW 12 O 40），Dawson型（H 6 P 2 W 18 O 62）和Preyssler型（H 14 [NaP 5 W 30 O 110]）磷钨酸被用作丙酮酸乙酯与乙酸酐的酰化反应，以液相合成α-乙酰氧基丙烯酸乙酯的催化剂。该化合物是具有高热耐久性和透明度的生物基聚合物的候选单体之一。催化性能与酸强度，质子数和磷钨酸的稳定性有关。值得注意的是，每单位摩尔催化剂的Preyssler型磷钨酸的性能高于Keggin型。
• New extraction procedure for protonated polyoxometalates prepared in aqueous-organic solution and characterisation of their catalytic ability
  作者：Tadaharu Ueda、Keisuke Yamashita、Ayumu Onda

  DOI：10.1016/j.apcata.2014.07.032

  日期：2014.9

  Although POMs prepared in aqueous-organic solutions have been reported to exhibit interesting chemical properties and may be efficient catalysts, they could not be isolated in their protonated form using the normal extraction method. In this study, a new procedure of isolating protonated POMs, [S2VxM18-xO62]((4+x)-) and [AsVxM12-xO40]((3+x)-) (M = Mo, W; x = 0-2), which were prepared in an aqueous-organic mixed solution, was developed by modifying and optimising the extraction conditions. Isolated protonated POMs were characterised using IR and Raman spectroscopy, and their acidity was measured using a Hammett indicator. The acidity of H4S2W18O62, H5S2VW17O62, H4S2Mo18O62, and H3As2W18O62 was stronger than that of H3PW12O40. Their catalytic ability was investigated in multiple types of organic reactions, including pinacol rearrangement, acetal formation with benzaldehyde and ethylene glycol, and the Friedel-Crafts acylation of anisole with ethyl pyruvate. They exhibited greater catalytic ability than commercially available POMs such as H3PM12O40 and H4SiM12O40 (M = Mo, W). (C) 2014 Elsevier B.V. All rights reserved.
• Sulfamic Acid as A Cost-Effective Catalyst for Synthesis of <font>α</font>-Acyloxyacrylate Esters as Candidate Monomers for Biobased Polymers by Acylation of Pyruvate Esters
  作者：Zhenxin Zhang、Baochun Ma、Qianqian Zhu、Yong Ding、Changming Wang、Wenfeng Song

  DOI：10.1080/00397911.2011.575521

  日期：2012.10.15

  Sulfamic acid was used as an efficient catalyst and green alternative for metal-containing acidic material to promote the acylation of pyruvate esters to produce alpha-acyloxyacrylate esters, which were candidate monomers for biobased polymers. Polymers from these monomers were useful materials for bio-based plastics, which showed high heat resistance and transparency. A series of alpha-acyloxyacrylate esters were converted from pyruvate esters by using sulfamic acid as a catalyst and good yields were obtained. The reaction in the presence of the sulfamic acid catalyst was carried out in the liquid phase and showed greater productivity than synthesis with a conventional liquid inorganic acid.
• An efficient heteropolyacid catalyzed acylation of pyruvate esters to α-acyloxyacrylate esters as potential candidate monomers for bio-based polymers
  作者：Wataru Ninomiya、Masahiro Sadakane、Shinji Matsuoka、Hiroki Nakamura、Hiroyuki Naitou、Wataru Ueda

  DOI：10.1039/b809940e

  日期：——

  α-Acyloxyacrylate esters were efficiently synthesized from pyruvate esters and carboxylic anhydrides under mild conditions. These esters are potential candidate monomers for bio-based polymers with high durability and transparency. Tungsten-based Keggin type heteropolyacids, especially H3PW12O40, worked more effectively as catalysts for this reaction than other typical acids.

  在温和条件下，由丙酮酸酯和羧酸酐有效合成α-酰氧基丙烯酸酯。这些酯是具有高耐久性和透明度的生物基聚合物的潜在候选单体。钨基 Keggin 型杂多酸，尤其是 H3PW12O40，作为该反应的催化剂比其他典型酸更有效。