3-bromoacrylonitrile | 41866-26-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 3-bromoacrylonitrile
• 英文别名: (E)-3-Bromoacrylonitrile；3-Bromacrylnitril；trans-3-Brom-acrylonitril；E-3-Bromacrylonitril；3-Brom-acrylonitril；(E)-3-bromoprop-2-enenitrile
• CAS: 41866-26-6
• 化学式: C₃H₂BrN
• 分子量: 131.96
• InChiKey: PCNPNEFEZSKSEK-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromoacrylonitrile 、 N-甲基-1-萘甲胺 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到N-methyl-N-(3-cyano-2-propenyl)-1-naphthalenemethanamine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics

  摘要：

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.

  DOI：

  10.1021/jm00151a019
• 作为产物：
  描述：

  (Z)-3-Bromopropenamide 在 phosphorus pentoxide 作用下， 生成 3-bromoacrylonitrile
  参考文献：
  名称：

  Gryszkiewicz-Trochimowski; Schmidt; Gryszkiewicz-Trochimowski, Bulletin de la Societe Chimique de France, 1948, p. 593,596

  摘要：

  DOI：

文献信息

• Reaction of activated vinyl halides with tervalent phosphorus nucleophiles
  作者：Gerald Pattenden、Brian J. Walker

  DOI：10.1039/j39690000531

  日期：——

  cis- and trans- Isomers of derivatives of 3-halogenoacrylic acids undergo nucleophilic displacement reactions with triphenylphosphine, tri-n-butylphosphine, and triethyl phosphite to produce the correspondingtrans-vinyl-phosphonium salts and -phosphonates exclusively. 1H n.m.r.spectra are reported for these compounds. The mechanism of the displacement reaction is discussed.

  3-卤代丙烯酸衍生物的顺式和反式异构体与三苯基膦，三正丁基膦和亚磷酸三乙酯进行亲核取代反应，仅生成相应的反式-乙烯基-盐和-膦酸酯。据报道这些化合物的1 H nmr光谱。讨论了置换反应的机理。
• Stereospecific alkylation of the Schiff base ester of alanine with 2-substituted-(E)- and -(Z)-vinyl bromides. An efficient synthesis of 2-methyl-(E)-3,4-didehydroglutamic acid, a potent substrate-induced irreversible inhibitor of L-glutamate-1-decarboxylase
  作者：Philippe Bey、Jean Paul Vevert

  DOI：10.1021/jo01304a021

  日期：1980.8
• Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics
  作者：Anton Stuetz、Apostolos Georgopoulos、Waltraud Granitzer、Gabor Petranyi、Daniel Berney

  DOI：10.1021/jm00151a019

  日期：1986.1

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.
• Gryszkiewicz-Trochimowski; Schmidt; Gryszkiewicz-Trochimowski, Bulletin de la Societe Chimique de France, 1948, p. 593,596
  作者：Gryszkiewicz-Trochimowski、Schmidt、Gryszkiewicz-Trochimowski

  DOI：——

  日期：——