furan-2-carboxylic acid N-allyl-N-benzylamide | 583052-91-9

• 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: furan-2-carboxylic acid N-allyl-N-benzylamide
• 英文别名: N-allyl-N-benzylfuran-2-carboxamide；N-Benzyl-N-(prop-2-en-1-yl)furan-2-carboxamide；N-benzyl-N-prop-2-enylfuran-2-carboxamide
• CAS: 583052-91-9
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: ZJFHJUDKVDBIMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  furan-2-carboxylic acid N-allyl-N-benzylamide 以 甲苯 为溶剂， 反应 3.0h， 生成 3-benzyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-2-one
  参考文献：
  名称：

  N-烯丙基2-糠酰酰胺的分子内Diels-Alder反应：空间应变和酰胺旋转异构现象的影响

  摘要：

  研究了氮原子上具有不同取代基的各种N-烯丙基2-呋喃酰酰胺的分子内Diels-Alder反应。与具有较小取代基的类似物相比，具有较大取代基的酰胺的反应进行得更快。从对取代基作用的系统实验研究以及基于B3LYP / 6-31G（d）水平DFT计算的能量评估得出，增强的反应性归因于环化后空间应变的减轻，而不是由酰胺旋转异构体控制庞大的取代基。

  DOI：

  10.1016/j.tetlet.2010.10.139
• 作为产物：
  描述：

  N-苄基呋喃-2-甲酰胺 、 3-溴丙烯 在 sodium hydroxide 、 (n-Bu₄)HSO₄ 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 49.0h， 以40%的产率得到furan-2-carboxylic acid N-allyl-N-benzylamide
  参考文献：
  名称：

  Intramolecular Cyclization Reactions of 5-Halo- and 5-Nitro-Substituted Furans

  摘要：

  [GRAPHICS]Intramolecular cyclization reactions of 5-halo- and 5-nitro-substituted furanylamides were examined. The 2-alkoxy-5-bromofuran derivative 2 produced the rearranged dihydroquinone 6 (36%), a product from the rearrangement of the intermediate oxabicycle 3. The 5-halo substituted furoyl amide 18 was converted to the polyfunctional oxabicycle 20 in 82% yield and at a much faster rate than the unsubstituted furanyl system 17. The 5-nitro-substituted furfuryl amide 33b underwent an unusual isomerization-cyclization reaction under microwave conditions to provide 1,4-dihydro-2H-benzo[4,5]furo[2,3-c]pyridin-3-one 34.

  DOI：

  10.1021/ol035233k

文献信息

• Intramolecular Cyclization Reactions of 5-Halo- and 5-Nitro-Substituted Furans
  作者：Kenneth R. Crawford、Scott K. Bur、Christopher S. Straub、Albert Padwa

  DOI：10.1021/ol035233k

  日期：2003.9.1

  [GRAPHICS]Intramolecular cyclization reactions of 5-halo- and 5-nitro-substituted furanylamides were examined. The 2-alkoxy-5-bromofuran derivative 2 produced the rearranged dihydroquinone 6 (36%), a product from the rearrangement of the intermediate oxabicycle 3. The 5-halo substituted furoyl amide 18 was converted to the polyfunctional oxabicycle 20 in 82% yield and at a much faster rate than the unsubstituted furanyl system 17. The 5-nitro-substituted furfuryl amide 33b underwent an unusual isomerization-cyclization reaction under microwave conditions to provide 1,4-dihydro-2H-benzo[4,5]furo[2,3-c]pyridin-3-one 34.
• Intramolecular Diels–Alder reaction of N-allyl 2-furoyl amides: effect of steric strain and amide rotational isomerism
  作者：Masashi Nakamura、Isao Takahashi、Shunsuke Yamada、Yasuo Dobashi、Osamu Kitagawa

  DOI：10.1016/j.tetlet.2010.10.139

  日期：2011.1

  Intramolecular Diels–Alder reactions of various N-allyl 2-furoyl amides with different substituents on the nitrogen atom were investigated. The reaction of amides having bulky substituents proceeded at a faster rate than the analogs whose substituents were of less bulkiness. From the systematic experimental survey of the substituent effects and the energetic evaluation based on the DFT calculations

  研究了氮原子上具有不同取代基的各种N-烯丙基2-呋喃酰酰胺的分子内Diels-Alder反应。与具有较小取代基的类似物相比，具有较大取代基的酰胺的反应进行得更快。从对取代基作用的系统实验研究以及基于B3LYP / 6-31G（d）水平DFT计算的能量评估得出，增强的反应性归因于环化后空间应变的减轻，而不是由酰胺旋转异构体控制庞大的取代基。