N-Trityl-3-butenamide | 132565-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-Trityl-3-butenamide
• 英文别名: CH2=CHCH2CONHTr；N-tritylbut-3-enamide
• CAS: 132565-57-2
• 化学式: C₂₃H₂₁NO
• 分子量: 327.426
• InChiKey: SOPZSZYDKWERTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  532.0±50.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Trityl-3-butenamide 在 三氟乙酸 、 三异丙基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到3-丁烯酰胺
  参考文献：
  名称：

  由α，β-不饱和酸合成β，γ-不饱和伯酰胺及其机理的研究

  摘要：

  α，β-不饱和酸，通过其酰氯，在温和的条件下，在三乙胺存在下与三苯甲基胺反应，以高收率和高区域选择性提供相应的β，γ-不饱和三苯乙酰胺。用TFA进行去三苯甲基化可定量生成β，γ-不饱和伯酰胺。对该解共轭异构化进行了研究。

  DOI：

  10.1016/j.tet.2011.05.096
• 作为产物：
  描述：

  2-丁烯酰氯 、 三苯甲胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-Trityl-3-butenamide
  参考文献：
  名称：

  由α，β-不饱和酸合成β，γ-不饱和伯酰胺及其机理的研究

  摘要：

  α，β-不饱和酸，通过其酰氯，在温和的条件下，在三乙胺存在下与三苯甲基胺反应，以高收率和高区域选择性提供相应的β，γ-不饱和三苯乙酰胺。用TFA进行去三苯甲基化可定量生成β，γ-不饱和伯酰胺。对该解共轭异构化进行了研究。

  DOI：

  10.1016/j.tet.2011.05.096

文献信息

• New synthesis of nitrogen heterocycles through amide-directed hydrocarbonylation of alkenamides catalyzed by rhodium complexes
  作者：Iwao Ojima、Anna Korda、William R. Shay

  DOI：10.1021/jo00006a013

  日期：1991.3

  Amide-directed hydrocarbonylation of 3-butenamide (1) catalyzed by rhodium complexes such as RhCl(PPh3)3, RhCl(CO)(PPh3)2, HRh(CO)(PPh3)3, and Rh4(CO)12 gives a mixture of 3,4-dihydro-2-pyridone (2), 4-methyl-3-pyrrolin-2-one (3), and a unique heterodimer, 6-(4-methyl-2-oxo-3-pyrrolin-1-yl)-2-piperidone (4). Dihydropyridone (2) is obtained in 88% yield with 98% selectivity by using HRh(CO)(PPh)3-dppb (2 equiv) catalyst system while 4 is yielded in 90% yield with 94% selectivity with the use of RhCl(PPh3)3-P(OPh)3 (10 equiv) as the catalyst. Control experiments revealed that this crossed coupling only proceeds in the copresence of rhodium catalyst, carbon monoxide, and hydrogen. The reactions of N-benzyl-3-butenamide (1a) gives a mixture of 1-benzyldihydropyridone (2a), 1-benzyl-4-methylpyrrolinone (3a), and 1-benzyl-6-formyl-3,4-dihydropyridone (5) and its 5-formyl isomer (6). The formation of 5 and 6 is suppressed by the addition of PPh3, and 2a is selectively isolated (72%) in the reaction using RhCl(CO)(PPh3)2-PPh3 (20 equiv) as the catalyst. The hydroformylation of 2a catalyzed by RhCl(PPh3)3 gives 5 in 80% isolated yield. The reaction of N-tert-butyl-3-butenamide (1b) gives a nearly 1:1 mixture of 1-tert-butyl-4-methylpyrrolinone (3b) and uncyclized N-tert-butyl-4-formylbutanamide (7) accompanied by a small amount of 1-tert-butyldihydropyridone (2b). In the reaction of N-trityl-3-butenamide (1c), no dihydropyridone (2c) was formed, and a mixture of 1-trityl-4-methylpyrrolinone (3c) (major) and N-trityl-4-formylbutanamide (8) (minor) is yielded. The reaction of 4-pentenamide gives 4-methyl-3,4-dihydro-2-pyridone (9) exclusively regardless of the structure of the rhodium catalysts used. Possible mechanisms for these reactions are discussed.
• Synthesis of β,γ-unsaturated primary amides from α,β-unsaturated acids and investigation of the mechanism
  作者：Vassiliki Theodorou、Marina Gogou、Maria Philippidou、Valentine Ragoussis、Georgios Paraskevopoulos、Konstantinos Skobridis

  DOI：10.1016/j.tet.2011.05.096

  日期：2011.8

  α,β-Unsaturated acids, through their acid chlorides, react with tritylamine in the presence of triethylamine under mild conditions, to afford in high yield and high regioselectivity the corresponding β,γ-unsaturated tritylamides. Detritylation with TFA generates quantitatively β,γ-unsaturated primary amides. An investigation of this deconjugative isomerization was performed.

  α，β-不饱和酸，通过其酰氯，在温和的条件下，在三乙胺存在下与三苯甲基胺反应，以高收率和高区域选择性提供相应的β，γ-不饱和三苯乙酰胺。用TFA进行去三苯甲基化可定量生成β，γ-不饱和伯酰胺。对该解共轭异构化进行了研究。