2,2-dipropanoyloxypropionic acid ethyl ester | 1092954-36-3

• 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: 2,2-dipropanoyloxypropionic acid ethyl ester
• 英文别名: Ethyl 2,2-di(propanoyloxy)propanoate
• CAS: 1092954-36-3
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: SFKUDSRUJFVZKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙酮酸乙酯 、 丙酸酐 在 phosphotungstic acid 、 丙酸 作用下， 反应 1.0h， 以56%的产率得到Ethyl 2-propanoyloxyprop-2-enoate
  参考文献：
  名称：

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

  摘要：

  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。

  DOI：

  10.1039/b914515j

文献信息

• 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。
• 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.