(allyloxycarbonyl)methyl cyanoacetate

• 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: (allyloxycarbonyl)methyl cyanoacetate
• 英文别名: (2-Oxo-2-prop-2-enoxyethyl) 2-cyanoacetate
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: KZEFCMMWZWLRKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (allyloxycarbonyl)methyl cyanoacetate 在 哌啶 、 phosphorus pentoxide 、 对甲苯磺酸 、 对苯二酚 作用下， 生成 allyloxycarbonylmethyl α-cyanoacrylate
  参考文献：
  名称：

  Synthesis of functionally substituted 2-cyanoacrylates

  摘要：

  The conditions for the Knoevenagel synthesis of 2-cyanoacrylates containing double and triple bonds in the alkoxycarbonyl group have been studied. It was found that the esters are formed in 10-70 % yields by the condensation of the respective cyanoacetates with formaldehyde in the 1 : 1 ratio in the presence of piperidine, followed by the pyrolysis of the oligomers formed in vacao at 170-200 degrees C in the presence of para-toluenesulfonic acid. The compounds synthesized readily undergo polymerization at room temperature and can be used as the basis for thermostable rapidly polymerizing adhesives.

  DOI：

  10.1007/bf00699831
• 作为产物：
  描述：

  氯乙酸丙烯酯 、 potassium cyanoacetate 在 三乙胺 作用下， 反应 1.0h， 以80%的产率得到(allyloxycarbonyl)methyl cyanoacetate
  参考文献：
  名称：

  Synthesis of functionally substituted cyanoacetates

  摘要：

  Some new cyanoacetates were synthesized and characterized. They are precursors for alpha-cyanoacrylates used as rapidly polymerized, cold-hardening adhesives.

  DOI：

  10.1007/bf00698435

文献信息

• Novel alpha-cyanoacrylate compound, method of preparing same and adhesive comprising same
  申请人：Kabushiki Kaisha Alpha Giken

  公开号：EP0127855A1

  公开（公告）日：1984-12-12

  a-cyanoacrylate compounds expressed by the following general formula: wherein R' desianates- and R2 designates alkyl groups, alkenyl groups or alkynyl groups of C1 to C4. These compounds are preferably synthesized by the reaction of the compounds expressed by the following general formula: wherein R' and R2 are same as the above described, with formaldehyde products and then the depolymerization of the resulting dehydrating condensation polymers. These compounds are effectively used as fast-setting adhesives.

  由以下通式表示的 a-氰基丙烯酸酯化合物： 其中 R' 表示烷基 和 R2 表示 C1 至 C4 的烷基、烯基或炔基。这些化合物最好通过以下通式表示的化合物反应合成： 其中 R' 和 R2 与上述相同，与甲醛产物反应，然后将得到的脱水缩合聚合物解聚。这些化合物可有效地用作速凝粘合剂。
• US4582648A
  申请人：——

  公开号：US4582648A

  公开（公告）日：1986-04-15
• Synthesis of functionally substituted cyanoacetates
  作者：T. I. Guseva、N. G. Senchenya、I. P. Gol'ding、K. A. Mager、Yu. G. Gololobov

  DOI：10.1007/bf00698435

  日期：1993.3

  Some new cyanoacetates were synthesized and characterized. They are precursors for alpha-cyanoacrylates used as rapidly polymerized, cold-hardening adhesives.
• Synthesis of functionally substituted 2-cyanoacrylates
  作者：T. I. Guseva、N. G. Senchenya、K. A. Mager、V. A. Tsyryapkin、Yu. G. Gololobov

  DOI：10.1007/bf00699831

  日期：1994.4

  The conditions for the Knoevenagel synthesis of 2-cyanoacrylates containing double and triple bonds in the alkoxycarbonyl group have been studied. It was found that the esters are formed in 10-70 % yields by the condensation of the respective cyanoacetates with formaldehyde in the 1 : 1 ratio in the presence of piperidine, followed by the pyrolysis of the oligomers formed in vacao at 170-200 degrees C in the presence of para-toluenesulfonic acid. The compounds synthesized readily undergo polymerization at room temperature and can be used as the basis for thermostable rapidly polymerizing adhesives.