N-(2-{[Allyl-(2,2,2-trifluoro-acetyl)-amino]-phenyl-methyl}-phenyl)-acrylamide | 210534-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-{[Allyl-(2,2,2-trifluoro-acetyl)-amino]-phenyl-methyl}-phenyl)-acrylamide
• 英文别名: N-[2-[phenyl-[prop-2-enyl-(2,2,2-trifluoroacetyl)amino]methyl]phenyl]prop-2-enamide
• CAS: 210534-47-7
• 化学式: C₂₁H₁₉F₃N₂O₂
• 分子量: 388.389
• InChiKey: RJFWEHKFIPTRMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-{[Allyl-(2,2,2-trifluoro-acetyl)-amino]-phenyl-methyl}-phenyl)-acrylamide 在 12-冠醚-4 、 三氟甲磺酸酐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.5h， 生成 (4aR,7S)-7-Phenyl-6-(2,2,2-trifluoro-acetyl)-3,4,4a,5,6,7-hexahydro-benzo[f]pyrido[1,2-a][1,4]diazepine-1-carbonitrile
  参考文献：
  名称：

  N-Phenyl-1-aza-2-cyano-1, 3-butadienes: An intramolecular hetero Diels-Alder strategy for the construction of 1, 4-benzodiazepines

  摘要：

  A new approach to the construction of tricyclic 1,4-benzodiazepines has been developed, based upon the intramolecular Diels-Alder (IMDA) reaction of 2-cyano-1-azadienes. This study revealed the difficulties inherent to the direct transformation of imine-amide 2 to azadiene 3, but demonstrated the efficiency of the intramolecular [4 + 2] cycloaddition of azadiene 13 as a means to access benzodiazepines 14a,b (3 : 2 mixture; 74% combined yield). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00756-4
• 作为产物：
  描述：

  N-(2-{[(E)-Allylimino]-phenyl-methyl}-phenyl)-acrylamide 在 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 N-(2-{[Allyl-(2,2,2-trifluoro-acetyl)-amino]-phenyl-methyl}-phenyl)-acrylamide
  参考文献：
  名称：

  N-Phenyl-1-aza-2-cyano-1, 3-butadienes: An intramolecular hetero Diels-Alder strategy for the construction of 1, 4-benzodiazepines

  摘要：

  A new approach to the construction of tricyclic 1,4-benzodiazepines has been developed, based upon the intramolecular Diels-Alder (IMDA) reaction of 2-cyano-1-azadienes. This study revealed the difficulties inherent to the direct transformation of imine-amide 2 to azadiene 3, but demonstrated the efficiency of the intramolecular [4 + 2] cycloaddition of azadiene 13 as a means to access benzodiazepines 14a,b (3 : 2 mixture; 74% combined yield). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00756-4

文献信息

• N-Phenyl-1-aza-2-cyano-1, 3-butadienes: An intramolecular hetero Diels-Alder strategy for the construction of 1, 4-benzodiazepines
  作者：Catherine Goulaouic-Dubois、David R. Adams、Nicholas J. Sisti、Frank W. Fowler、David S. Grierson

  DOI：10.1016/s0040-4039(98)00756-4

  日期：1998.6

  A new approach to the construction of tricyclic 1,4-benzodiazepines has been developed, based upon the intramolecular Diels-Alder (IMDA) reaction of 2-cyano-1-azadienes. This study revealed the difficulties inherent to the direct transformation of imine-amide 2 to azadiene 3, but demonstrated the efficiency of the intramolecular [4 + 2] cycloaddition of azadiene 13 as a means to access benzodiazepines 14a,b (3 : 2 mixture; 74% combined yield). (C) 1998 Elsevier Science Ltd. All rights reserved.