氰基丙烯酸酯 | 1027379-53-8

• 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
• 中文名称: 氰基丙烯酸酯
• 英文名称: cyano acrylate
• 英文别名: Acrylcyanate；cyano prop-2-enoate
• CAS: 1027379-53-8
• 化学式: C₄H₃NO₂
• 分子量: 97.0733
• InChiKey: NLCKLZIHJQEMCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氰基丙烯酸酯 、 苯胺 在 aluminium incorporated mesoporous aluminosilicate nano-cage material 作用下， 以 neat (no solvent) 为溶剂， 反应 6.0h， 以10%的产率得到4-(苯基氨基)丁腈
  参考文献：
  名称：

  Room temperature solvent free aza-Michael reactions over nano-cage mesoporous materials

  摘要：

  An efficient highly acidic three dimensional mesoporous aluminosilicate nano-cage material A1-KIT5, exhibited excellent catalytic activity in solvent free room temperature aza-Michael reactions of amines with alpha,beta-unsaturated carbonyl compounds to produce beta-amino carbonyl compounds with 100% product selectivity in a short reaction time. The high acidity, 3D pores, and a huge space in the nano-cages materials make them attractive candidate for carrying out important organic reactions. The catalyst provide a simple, easy to handle method, and could be used to solve the problems of corrosion, toxicity, waste production, and a high cost that are being currently encountered by the conventional homogeneous catalysts. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2014.06.031
• 作为试剂：
  描述：

  1,4-二氧六环 、 、 氰乙酸正丁酯 、 丙烯醛 在 氯化锌 crude product 、 二氯甲烷 、 NaSO4 、 氰基丙烯酸酯 作用下， 以 盐酸 为溶剂， 反应 65.0h， 生成 2-Cyano-2,4-pentadienoic Acid Butylester
  参考文献：
  名称：

  DENTAL COMPOSITION

  摘要：

  一种牙科组合物，包括单体和/或聚合物的氰基丙酸酯，可聚合单体，稳定剂，引发剂，以及可选的颜料和填充材料。

  公开号：

  US20020025993A1

文献信息

• Fused pyrrolocarbazoles
  申请人：Cephalon, Inc.

  公开号：US05591855A1

  公开（公告）日：1997-01-07

  Disclosed herein are compounds referred to as "fused pyrrolocarbazoles" which possess a variety of functional activities. The disclosed compounds are represented by the following general formula: ##STR1## Methodologies for the synthetic production of fused pyrrolocarbazoles are also disclosed, as well as exemplary uses of the compounds.

  本文披露了一些被称为“融合吡咯咔唑”的化合物，这些化合物具有多种功能活性。所披露的化合物由以下通用公式表示：##STR1## 还披露了合成融合吡咯咔唑的方法，以及化合物的示例用途。
• Preparation of bis (2-cyanoacrylate)monomers
  申请人：Johnson & Johnson

  公开号：US03975422A1

  公开（公告）日：1976-08-17

  Difunctional monomers of the formula, ##EQU1## where R is an organic linking group derived from a diol or a dihalide of the formula X-R-X, where X is either chlorine, bromine, iodine, or hydroxy, are prepared by reacting a conjugated diene, exemplified by anthracene, with an ester of 2-cyanoacrylic acid to form the Diels-Alder adduct of the ester. The ester adduct is hydrolyzed to ultimately obtain either the Diels-Alder adduct of either 2-cyanoacrylic acid--alkali metal salt or 2-cyanoacryloyl halide. These latter intermediates are respectively reacted with either the dihalide or the diol to afford the bis-Diels-Alder adduct of the R substituted bis (2-cyanoacrylate) monomer. The protective diene group may then be removed, for example, by reaction with excess maleic anhydride and the resulting difunctional monomer isolated. The difunctional monomers thus prepared can be utilized as crosslinking agents in blends comprising one or more of these difunctional monomers and at least one monofunctional monomer, exemplified by an ester of 2-cyanoacrylic acid. Alternately, one or more difunctional monomers can be homopolymerized or copolymerized to a highly crosslinked polymer. The copolymerized compositions of the monomer blends are particularly useful as adhesives, especially in dental applications for coating or sealing enamel surfaces of teeth to allay decay, or for the bonding of brackets to teeth in orthodontics the bond being substantially more resistant to moisture than where the monofunctional monomer is used alone.

  本发明涉及一种公式为##EQU1##的双官能团单体，其中R是源自二醇或公式X-R-X的二卤代物的有机连接基，其中X是氯、溴、碘或羟基。该方法通过将一个共轭二烯与2-氰基丙烯酸酯反应形成酯的Diels-Alder加合物来制备该双官能团单体。酯加合物水解后最终得到2-氰基丙烯酸-碱金属盐或2-氰基丙烯酰卤的Diels-Alder加合物。这些后者中间体分别与二卤代物或二醇反应，以得到R取代的双(2-氰基丙烯酸酯)单体的双Diels-Alder加合物。然后可以通过与过量马来酸酐反应来去除保护的二烯基基团，并分离所得的双官能团单体。因此制备的双官能团单体可以用作交联剂，包括至少一种双官能团单体和至少一种单官能团单体的混合物。另外，一个或多个双官能团单体可以进行均聚或共聚，形成高度交联的聚合物。共聚物混合物的组成物尤其适用于粘合剂，特别是在牙科应用中用于涂覆或密封牙齿的珐琅质表面以防止腐烂，或用于在正畸学中将支架粘合到牙齿上，其粘合强度比仅使用单官能团单体时更能抵抗潮湿。
• Blocked bis 2-cyanoacrylate monomers
  申请人：Johnson & Johnson

  公开号：US04003942A1

  公开（公告）日：1977-01-18

  Difunctional monomers of the formula, ##STR1## where R is an organic linking group derived from a diol or a dihalide of the formula X--R--X, where X is either chlorine, bromine, iodine, or hydroxy, are prepared by reacting a conjugated diene, exemplified by anthracene, with an ester of 2-cyanoacrylic acid to form the Diels-Alder adduct of the ester. The ester adduct is hydrolyzed to ultimately obtain either the Diels-Adler adduct of either 2-cyanoacrylic acid--alkali metal salt or 2-cyanoacryloyl halide. These latter intermediates are respectively reacted with either the dihalide or the diol to afford the bis-Diels-Alder adduct of the R substituted bis (2-cyanoacrylate) monomer. The protective diene group may then be removed, for example, by reaction with excess maleic anhydride and the resulting difunctional monomer isolated. The difunctional monomers thus prepared can be utilized as crosslinking agents in blends comprising one or more of these difunctional monomers and at least one monofunctional monomer, exemplified by an ester of 2-cyanoacrylic acid. Alternately, one or more difunctional monomers can be homopolymerized or copolymerized to a highly crosslinked polymer. The copolymerized compositions of the monomer blends are particularly useful as adhesives, especially in dental applications for coating or sealing enamel surfaces of teeth to allay decay, or for the bonding of brackets to teeth in orthodontics and bond being substantially more resistant to moisture than where the monofunctional monomer is used alone.

  公式为##STR1##的二官能单体，其中R是源自二醇或二卤化物（X-R-X）的有机连接基，其中X可以是氯、溴、碘或羟基。通过反应共轭二烯，例如蒽，与2-氰基丙烯酸酯的酯形成Diels-Alder加合物来制备这些二官能单体。酯加合物被水解，最终获得2-氰基丙烯酸-碱金属盐或2-氰基丙烯酰卤的Diels-Adler加合物。分别用这些后继体与二卤化物或二醇反应，得到R取代的双Diels-Alder加合物的双(2-氰基丙烯酸酯)单体。然后可以去除保护二烯基团，例如通过与过量马来酸酐反应，并分离得到所得的二官能单体。因此制备的二官能单体可以用作交联剂，用于混合物，包括一个或多个这些二官能单体和至少一个单官能单体，例如2-氰基丙烯酸酯。或者，可以将一个或多个二官能单体进行均聚或共聚形成高度交联的聚合物。单体混合物的共聚物组合物特别适用于粘合剂，特别是在牙科应用中用于涂覆或密封牙釉质表面以减轻腐烂，或用于在正畸学中将托槽粘接到牙齿上，这种粘合剂对水分的抵抗性比单官能单体单独使用时更强。
• Modified cyanoacrylate monomers and methods for preparation
  申请人：Johnson & Johnson

  公开号：US04012402A1

  公开（公告）日：1977-03-15

  Difunctional monomers of the formula, ##STR1## where R is an organic linking group derived from a diol or a dihalide of the formula X-R-X, where X is either chlorine, bromine, iodine, or hydroxy, are prepared by reacting a conjugated diene, exemplified by anthracene, with an ester of 2-cyanoacrylic acid to form the Diels-Alder adduct of the ester. The ester adduct is hydrolyzed to ultimately obtain either the Diels-Alder adduct of either 2-cyanoacrylic acid--alkali metal salt of 2-cyanoacryloyl halide. These latter intermediates are respectively reacted with either the dihalide or the diol to afford the bis-Diels-Alder adduct of the R substituted bis (2-cyanoacrylate) monomer. The protective diene group may then be removed, for example, by reaction with excess maleic anhydride and the resulting difunctional monomer isolated. The difunctional monomers thus prepared can be utilized as crosslinking agents in blends comprising one or more of these difunctional monomers and at least one monofunctional monomer, exemplified by an ester of 2-cyanoacrylic acid. Alternately, one or more difunctional monomers can be homopolymerized or copolymerized to a highly crosslinked polymer. The copolymerized compositions of the monomer blends are particularly useful as adhesives, especially in dental applications for coating or sealing enamel surfaces of teeth to allay decay, or for the bonding of brackets to teeth in orthodontics the bond being substantially more resistant to moisture than where the monofunctional monomer is used alone.

  本发明涉及一种公式为##STR1##的二元单体，其中R是从公式X-R-X中的二元醇或二卤代物(X为氯、溴、碘或羟基)导出的有机连接基，通过将一个共轭二烯，例如蒽，与2-氰基丙烯酸酯反应形成酯的Diels-Alder加合物来制备。酯加合物水解后最终得到2-氰基丙烯酸的Diels-Alder加合物-2-氰基丙烯酰卤化物的碱金属盐。这些后续中间体分别与二卤代物或二元醇反应，以得到R取代的双Diels-Alder加合物的2-氰基丙烯酸酯单体。然后可以通过与过量马来酸酐反应来去除保护的二烯基基团，并分离所得的二元单体。这样制备的二元单体可以用作交联剂，与至少一种单官能单体混合，例如2-氰基丙烯酸酯。或者，一个或多个二元单体可以进行均聚或共聚，形成高度交联的聚合物。共聚物化的单体混合物尤其适用于粘合剂，特别是在牙科应用中，用于涂覆或密封牙齿的珐琅质表面以防止腐烂，或用于在正畸学中将托槽粘接到牙齿上，其粘接比仅使用单官能单体时更具有抗潮湿性。
• Cyanoacrylic acid adducts
  申请人：Johnson & Johnson

  公开号：US04013703A1

  公开（公告）日：1977-03-22

  Difunctional monomers of the formula, ##STR1## where R is an organic linking group derived from a diol or a dihalide of the formula X-R-X, where X is either chlorine, bromine, iodine, or hydroxy, are prepared by reacting a conjugated diene, exemplified by anthracene, with an ester of 2-cyanoacrylic acid to form the Diels-Alder adduct of the ester. The ester adduct is hydrolyzed to ultimately obtain either the Diels-Alder adduct of either 2-cyanoacrylic acid--alkali metal salt or 2-cyanoacryloyl halide. These later intermediates are respectively reacted with either the dihalide or the diol to afford the bis-Diels-Alder adduct of the R substituted bis (2-cyanoacrylate) monomer. The protective diene group may then be removed, for example, by reaction with excess maleic anhydride and the resulting difunctional monomer isolated. The difunctional monomers thus prepared can be utilized as crosslinking agents in blends comprising one or more of these difunctional monomers and at least one monofunctional monomer, exemplified by an ester of 2-cyanoacrylic acid. Alternately, one or more difunctional monomers can be homopolymerized or copolymerized to a highly crosslinked polymer. The copolymerized compositions of the monomer blends are particularly useful as adhesives, especially in dental applications for coating or sealing enamel surfaces of teeth to allay decay, or for the bonding of brackets to teeth in orthodontics the bond being substantially more resistant to moisture than where the monofunctional monomer is used alone.

  本文介绍了一种制备二元功能单体的方法，其化学式为##STR1##其中R为有机连接基，来自于化学式X-R-X的二醇或二卤代物，其中X为氯、溴、碘或羟基。该方法通过将一个共轭二烯与2-氰基丙烯酸酯反应形成Diels-Alder加合物，再将该酯加合物水解，最终得到2-氰基丙烯酸-碱金属盐或2-氰基丙烯酰卤的Diels-Alder加合物。然后，将这些中间体分别与二卤代物或二醇反应，得到R取代的双Diels-Alder加合物的bis（2-氰基丙烯酸酯）单体。可以通过与过量马来酸酐反应来去除保护二烯基团，并分离得到所得的二元功能单体。这些制备的二元功能单体可以用作交联剂，与至少一种单元功能单体混合物，例如2-氰基丙烯酸酯。或者，可以将一种或多种二元功能单体进行均聚或共聚，形成高度交联的聚合物。共聚物混合物的组成在粘合剂中特别有用，特别是在牙科应用中，用于涂覆或密封牙齿表面以防止腐烂，或用于在正畸学中将支架粘合到牙齿上，其粘合比单元功能单体单独使用时更具有抗潮湿性。