N-allylthioacetamide | 56634-59-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 英文名称: N-allylthioacetamide
• 英文别名: N-allyl-thioacetamide；N-Allyl-thioacetamid；Thioessigsaeure-allylamid；N-Allyl-acetthionamid；N-prop-2-enylethanethioamide
• CAS: 56634-59-4
• 化学式: C₅H₉NS
• mdl: MFCD19217814
• 分子量: 115.199
• InChiKey: YFMAKCFHZPNRMH-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：
  0.4
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allylthioacetamide 、 苯基溴化硒 以 氯仿 为溶剂， 反应 3.0h， 以87%的产率得到2-Methyl-5-(phenylselanylmethyl)-4,5-dihydro-1,3-thiazole
  参考文献：
  名称：

  Organoselenium- and proton-mediated cyclization reactions of allylic amides and thioamides. Syntheses of 2-oxazolines and 2-thiazolines

  摘要：

  A variety of allylic amides and thioamides were treated with phenylselenenyl bromide in chloroform to give, via 5-exo cyclization, 2-oxazolines and 2-thiazolines, respectively, carrying a (phenylselenenyl)methyl substituent in the 5-position. In some cases (N-crotyl- and N-cinnamylamides/thioamides), dihydro-1,3-oxazines/-thiazines were formed via 6-endo cyclization. The phenylselenenyl group of the cyclofunctionalization products was slowly eliminated by treatment with m-chloroperbenzoic acid to introduce unsaturation in the resulting oxazoline/thiazoline. Reductive removal of the phenylselenenyl group was effected by treatment with triphenyltin hydride. This reaction was sometimes accompanied by a rearrangement of the heterocyclic ring. Proton-induced cyclizations of allylic thioamides to give 2-thiazolines was slowly but efficiently effected in boiling toluene containing a catalytic amount of p-toluenesulfonic acid.

  DOI：

  10.1021/jo00010a045
• 作为产物：
  描述：

  N-烯丙基乙酰胺 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到N-allylthioacetamide
  参考文献：
  名称：

  Organoselenium- and proton-mediated cyclization reactions of allylic amides and thioamides. Syntheses of 2-oxazolines and 2-thiazolines

  摘要：

  A variety of allylic amides and thioamides were treated with phenylselenenyl bromide in chloroform to give, via 5-exo cyclization, 2-oxazolines and 2-thiazolines, respectively, carrying a (phenylselenenyl)methyl substituent in the 5-position. In some cases (N-crotyl- and N-cinnamylamides/thioamides), dihydro-1,3-oxazines/-thiazines were formed via 6-endo cyclization. The phenylselenenyl group of the cyclofunctionalization products was slowly eliminated by treatment with m-chloroperbenzoic acid to introduce unsaturation in the resulting oxazoline/thiazoline. Reductive removal of the phenylselenenyl group was effected by treatment with triphenyltin hydride. This reaction was sometimes accompanied by a rearrangement of the heterocyclic ring. Proton-induced cyclizations of allylic thioamides to give 2-thiazolines was slowly but efficiently effected in boiling toluene containing a catalytic amount of p-toluenesulfonic acid.

  DOI：

  10.1021/jo00010a045

文献信息

• Photoinduced reactions—LXXIX
  作者：T. Matsuura、Y. Ito

  DOI：10.1016/0040-4020(75)80164-5

  日期：1975.1

  2537 Å 2-alkyl-2-thiazolines (1) underwent rearrangement to N-alkenylthioamides (2 and 3) as the major pathway and fragmentation to a nitrile and an episulphide as the minor one. Evidence is provided for the intermediary formation of a valence bond isomer, N-thioacylaziridine, followed by its photochemical transformation into N-alkenylthioamides.

  在2537Å的光照射下，2-烷基-2-噻唑啉（1）重排为主要途径的N-烯基硫酰胺（2和3），并碎裂为次要的腈和环硫化物。为中间形成价键异构体N-硫代酰基氮丙啶提供了证据，然后将其光化学转化为N-烯基硫代酰胺。
• Transamidation of thioacetamide catalyzed by SbCl3
  作者：Andrea Ojeda-Porras、Diego Gamba-Sánchez

  DOI：10.1016/j.tetlet.2015.05.067

  日期：2015.7

  A transamidation reaction of thioacetamide with primary and secondary amines is described. The use of catalytic amounts of SbCl3 notably increases the yields and diminishes the reaction times. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. This is one of the few examples where antimony has been used as a catalyst in organic reactions. (c) 2015 Elsevier Ltd. All rights reserved.
• Sachs; Loevy, Chemische Berichte, 1904, vol. 37, p. 875
  作者：Sachs、Loevy

  DOI：——

  日期：——
• The Cyclization of N-Alkenylthionamides to Thiazolines and Dihydrothiazines
  作者：PETER A. S. SMITH、JOHN M. SULLIVAN

  DOI：10.1021/jo01063a038

  日期：1961.4
• Organoselenium- and proton-mediated cyclization reactions of allylic amides and thioamides. Syntheses of 2-oxazolines and 2-thiazolines
  作者：Lars Engman

  DOI：10.1021/jo00010a045

  日期：1991.5

  A variety of allylic amides and thioamides were treated with phenylselenenyl bromide in chloroform to give, via 5-exo cyclization, 2-oxazolines and 2-thiazolines, respectively, carrying a (phenylselenenyl)methyl substituent in the 5-position. In some cases (N-crotyl- and N-cinnamylamides/thioamides), dihydro-1,3-oxazines/-thiazines were formed via 6-endo cyclization. The phenylselenenyl group of the cyclofunctionalization products was slowly eliminated by treatment with m-chloroperbenzoic acid to introduce unsaturation in the resulting oxazoline/thiazoline. Reductive removal of the phenylselenenyl group was effected by treatment with triphenyltin hydride. This reaction was sometimes accompanied by a rearrangement of the heterocyclic ring. Proton-induced cyclizations of allylic thioamides to give 2-thiazolines was slowly but efficiently effected in boiling toluene containing a catalytic amount of p-toluenesulfonic acid.