β-amino-acrylonitrile | 24532-83-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: β-amino-acrylonitrile
• 英文别名: 3-amino-acrylonitrile；β-aminoacrylonitrile；3-aminoacrylonitrile；(E)-3-aminoprop-2-enenitrile
• CAS: 24532-83-0
• 化学式: C₃H₄N₂
• 分子量: 68.0782
• InChiKey: RORTUEWWZUJHTM-OWOJBTEDSA-N

物化性质

• 沸点：
  292.0±13.0 °C(Predicted)
• 密度：
  0.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  β-amino-acrylonitrile 、 噻唑烷盐酸盐 以 乙腈 为溶剂， 反应 2.0h， 以25%的产率得到2,3,4,7-tetrahydro[1,4]thiazepine-6-carbonitrile
  参考文献：
  名称：

  Synthesis of 2,3,4,7-tetrahydro[1,4]thiazepines from thiazolidines and β-enaminonitriles

  摘要：

  A wide library of 2,3,4,7-tetrahydrol 1,4]thiazepines have been prepared by simple heating of thiazolidine and beta-enaminonitrile derivatives in acetonitrile. The procedure, whose yields depend on the nature and position of the Substituents, gave good results if the substituents were not very bulky but it is less effective when starting from 2-substituted thiazolidines. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.027
• 作为产物：
  描述：

  (Z)-3-aminoprop-2-enenitrile 以 四氢呋喃 为溶剂， 生成 β-amino-acrylonitrile
  参考文献：
  名称：

  Chemie vonα-氨基三烯。12. Mitteilung。Sondierungenüberthermische Umwandlungen vonα-Aminonitrilen †

  摘要：

  α-氨基腈的化学1 。α-氨基腈热反应的探索性实验

  DOI：

  10.1002/hlca.19940770814

文献信息

• Method of preparing .beta.-alkoxyacrlonitriles
  申请人：Dynamit Nobel Aktiengesellschaft

  公开号：US04319024A1

  公开（公告）日：1982-03-09

  A process for the preparation of a .beta.-alkoxyacrylonitrile of the formula R'O--CH.dbd.CR--CN (C) where R is hydrogen or an alkyl moiety, among others, by contacting a compound of the formula (1/.alpha.Me) O--CH.dbd.CR--CN (A) where Me is an alkali metal or alkaline earth metal and .alpha. is 1 or 2 respectively, an elevated temperature with a halogen compound of the formula R'Hal (B) where R' is among others a straight or branched alkyl or alkenyl moiety and Hal represents chlorine, bromine, or iodine. Also disclosed is a process for preparing a 3-amino-acrylonitrile of the formula ##STR1## where R.sup.5 and R.sup.6 represent, among others, hydrogen, alkyl or alkenyl by contacting a 3-alkoxyacrylonitrile or a metal salt of 3-hydroxyacrylonitrile with ammonia and/or amine. Also disclosed is a process for the preparation of such 3-aminoacrylonitrile by contacting a 3-alkoxyacrylonitrile of the formula ##STR2## where R' has the meaning given above and R.sup.7 has the same meaning as R stated above with an amine of the formula ##STR3## wherein R.sup.5 and R.sup.6 represent among others hydrogen, alkyl or alkenyl. The application further discloses a process for preparing a 3-amino-acrylonitrile of the formula ##STR4## where R.sup.5, R.sup.6 and R.sup.7 have the above meanings by contacting a compound of the formula ##EQU1## with an amine. The Application also discloses the preparation of two-cyanovinyl esters by reaction of a cyanovinyl compound of the formula ##EQU2## with an acid halide or an acid anhydride.

  一种制备β-烷氧基丙烯腈的过程，其化学式为R'O--CH.dbd.CR--CN（C），其中R为氢或烷基基团等，通过将化合物的化学式为（1/α.Me）O--CH.dbd.CR--CN（A）（其中Me为碱金属或碱土金属，α分别为1或2）与化学式为R'Hal（B）的卤素化合物在高温下接触而得到，其中R'为直链或支链烷基或烯基基团等，Hal代表氯、溴或碘。还公开了一种通过将3-烷氧基丙烯腈或3-羟基丙烯腈的金属盐与氨和/或胺接触而制备3-氨基丙烯腈的过程，其化学式为##STR1##其中R.sup.5和R.sup.6代表氢、烷基或烯基等。还公开了一种通过将具有上述给定含义的R'和R.sup.7与具有化学式##STR3##的胺接触而制备这种3-氨基丙烯腈的过程，其中R.sup.5和R.sup.6代表氢、烷基或烯基等。该申请还公开了一种通过将具有上述含义的R.sup.5、R.sup.6和R.sup.7的化合物与具有化学式##EQU1##的胺接触而制备3-氨基丙烯腈的过程。该申请还公开了通过将具有化学式##EQU2##的氰基乙烯化合物与酸卤或酸酐反应来制备二氰基乙烯酯的方法。
• Regioselectivity of the Photochemical Addition of Ammonia, Phosphine, and Silane to Olefinic and Acetylenic Nitriles
  作者：Jean-Claude Guillemin、Curt M. Breneman、Jeffrey C. Joseph、James P. Ferris

  DOI：10.1002/(sici)1521-3765(19980615)4:6<1074::aid-chem1074>3.0.co;2-b

  日期：1998.6.15
• Chemie von ?-Aminonitrilen. 12. Mitteilung. Sondierungen �ber thermische Umwandlungen von ?-Aminonitrilen
  作者：Yi-Bin Xiang、Susanne Drenkard、Karl Baumann、Deirde Hickey、Albert Eschenmoser

  DOI：10.1002/hlca.19940770814

  日期：1994.12.14

  Chemistry of α-Amino Nitriles1 . Exploratory Experiments on Thermal Reactions of α-Amino Nitriles

  α-氨基腈的化学1 。α-氨基腈热反应的探索性实验
• Synthesis of 2,3,4,7-tetrahydro[1,4]thiazepines from thiazolidines and β-enaminonitriles
  作者：Luis A. Calvo、Alfonso González-Ortega、Rocío Marcos、Mónica Pérez、M. Carmen Sañudo

  DOI：10.1016/j.tet.2008.02.027

  日期：2008.4

  A wide library of 2,3,4,7-tetrahydrol 1,4]thiazepines have been prepared by simple heating of thiazolidine and beta-enaminonitrile derivatives in acetonitrile. The procedure, whose yields depend on the nature and position of the Substituents, gave good results if the substituents were not very bulky but it is less effective when starting from 2-substituted thiazolidines. (c) 2008 Elsevier Ltd. All rights reserved.