N-[(E)-butadienyl]-N-isopropylpropanamide | 152710-47-9

• 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
• 英文名称: N-[(E)-butadienyl]-N-isopropylpropanamide
• 英文别名: N-[(1E)-buta-1,3-dienyl]-N-propan-2-ylpropanamide
• CAS: 152710-47-9
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: KTKVSTDPTCUNCR-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[(E)-butadienyl]-N-isopropylpropanamide 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (3R,4aS,8aR)-1-Isopropyl-3,4a-dimethyl-4a,5,6,8a-tetrahydro-1H-quinoline-2,4-dione
  参考文献：
  名称：

  制备和的级联反应Ñ -butadienyl- Ñ -alkylketene Ñ，ö -叔丁基二甲基缩醛

  摘要：

  的制备Ñ -butadienyl- Ñ -alkylketene Ñ，ö -叔丁基二甲基缩醛（11A - d）从容易获得的原料进行说明。级联Diels-Alder反应，然后将这些烯酮缩醛酰化，可得到具有高非对映选择性的双环和三环产物7.13a，b和14c，d。

  DOI：

  10.1016/0040-4020(96)00646-1
• 作为产物：
  描述：

  (E,E)-N-Isopropyl-1-aza-1,3-pentadien 、 丙酰氯 在 N,N-二乙基苯胺 作用下， 以 甲苯 为溶剂， 生成 N-[(E)-butadienyl]-N-isopropylpropanamide
  参考文献：
  名称：

  制备和的级联反应Ñ -butadienyl- Ñ -alkylketene Ñ，ö -叔丁基二甲基缩醛

  摘要：

  的制备Ñ -butadienyl- Ñ -alkylketene Ñ，ö -叔丁基二甲基缩醛（11A - d）从容易获得的原料进行说明。级联Diels-Alder反应，然后将这些烯酮缩醛酰化，可得到具有高非对映选择性的双环和三环产物7.13a，b和14c，d。

  DOI：

  10.1016/0040-4020(96)00646-1

文献信息

• Preparation of N-Alkylketene-N-Butadienyl-N,O-Silyl Acetals
  作者：Andreas Franz、Pierre-Yves Eschler、Manuel Tharin、Helen Stoeckli-Evans、Reinhard Neier

  DOI：10.1055/s-1996-4359

  日期：1996.10

  The synthesis of a series of dienamides 5a-j using Oppolzer’s method is described. Using Rathke’s method the ketene N,O-silyl acetals 6a-j can be obtained in good yield from the corresponding dienamines. The ketene acetals are obtained free of base and free of salts. They are stable and can be stored at -20°C. The new dienes are useful reagents for tandem reactions.

  描述了一系列二烯酰胺 5a-j 的合成，采用 Oppolzer 方法。通过 Rathke 方法，可以从相应的二烯胺中以良好的产率获得酮烯 N,O-硅醚 6a-j。这些酮烯醚不含碱和盐，可自由获得。它们稳定，可以在 -20°C 下存储。这些新型二烯是串联反应的有用试剂。
• ——
  作者：Klaus Neuschütz、Jean-Mary Simone、Thomas Thyrann、Reinhard Neier

  DOI：10.1002/1522-2675(20001004)83:10<2712::aid-hlca2712>3.0.co;2-d

  日期：2000.10.4

  We report the synthesis of N-benzyl-N-[(E)-buta-1,3-dienyl]propanamide (6) and its corresponding O-silyl-subitituted ketene N,O-acetal 7 and their Diels-Alder reaction. Propanamide G reacted smoothly, whereas the yield obtained from 7 was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals 27a-g were synthesized starting from the corresponding benzamides 25a-e (Scheme 9). The ketene N,O-acetals 27a-g showed increased stabilities and underwent amino-Claisen rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems, rac-35-37 or to a beta -lactam rac-34 were observed.
• The preparation and the cascade reactions of N-butadienyl-N-alkylketeneN,O-tert-butyldimethylsilyl acetals
  作者：Andreas Franz、Pierre-Yves Eschler、Manuel Tharin、Reinhard Neier

  DOI：10.1016/0040-4020(96)00646-1

  日期：1996.8

  The preparation of N-butadienyl-N-alkylketene N,O-tert-butyldimethylsilyl acetals (11a - d)from readily available starting materials is described. The cascade Diels-Alder reaction followed by acylation of these ketene acetals yields bicyclic and tricyclic products 7.13a,b and 14c,d with high diastereoselectivity.

  的制备Ñ -butadienyl- Ñ -alkylketene Ñ，ö -叔丁基二甲基缩醛（11A - d）从容易获得的原料进行说明。级联Diels-Alder反应，然后将这些烯酮缩醛酰化，可得到具有高非对映选择性的双环和三环产物7.13a，b和14c，d。
• Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions
  作者：Yves Rubin、Padma S. Ganapathi、Andreas Franz、Yi-Zhong An、Wenyuan Qian、Reinhard Neier

  DOI：10.1002/(sici)1521-3765(19991105)5:11<3162::aid-chem3162>3.0.co;2-h

  日期：1999.11.5

  We have studied the reactivity of the N,O-ketene N-1,3-butadienyl-N-alkyl-O-silyl acetals 1a-e with C-60 proceeding through a tandem process to give the adducts 2a-e, The addition order of these tandem reactions has been evaluated. The initial nucleophilic Michael-like addition of the electron-rich N,O-ketene acetal moiety proceeds unusually fast at 25 degrees C, followed by an intramolecularly accelerated Diels-Alder step that is highly diastereoselective. The structures of compounds 2a-e were determined from the H-1 and C-13 NMR shifts and from II-II coupling patterns, while their stereochemistry was deduced from 2D T-ROESY NMR experiments. The proposed mechanism for the nucleophilic addition involves single electron transfer followed by radical anion-radical cation recombination. Computational investigations of the reaction pathways, transition states, and conformational energies have been carried out to corroborate the experimental data.