N-(2-trans-Butenyl)-N-phenyl-1-amino-2-acetophenone | 150630-83-4

• 英文名称: N-(2-trans-Butenyl)-N-phenyl-1-amino-2-acetophenone
• 英文别名: 2-(N-[(E)-but-2-enyl]anilino)-1-phenylethanone
• CAS: 150630-83-4
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: OPNHUCPCZIEJJK-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2-trans-Butenyl)-N-phenyl-1-amino-2-acetophenone 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 15.0h， 生成 1,7-Diphenyl-4-methyl-3-oxa-2,7-diazabicyclo<3.3.0>octane
  参考文献：
  名称：

  Stereochemistry. 82. Conformation of fused five-membered heterocyclic rings derived from the intramolecular oxime olefin cycloaddition reaction

  摘要：

  Thermal intramolecular oxime olefin cycloaddition Of alpha-allylamino aldoximes and ketoximes 4 led stereospecifically to formation of oxadiazabicyclo[3.3.0]octanes 6. The presence of heteroatoms in these bicyclic fused 5-membered rings permits for the first time an evaluation of the conformation of this system by means of NMR. We found that some substituents in 6 restrict the conformational mobility of these five-membered rings to the extent that only one conformer was detected at 20-degrees-C. In other cases an equilibrium between two major conformers was revealed by NMR. Equilibrium measurements indicated a free energy of conversion of 13.2-13.4 kcal/mol, apparently a manifestation of the N-inversion in the isoxazolidine ring. NMR studies also showed that the NH-proton in isoxazolidines 6 prefers an axial orientation. Empirical force field data were adjusted for MM calculations in these bicyclic heterocycles. The MM2 force field with AMBER charge gave the best fit between calculated and experimental coupling constants.

  DOI：

  10.1021/jo00069a011
• 作为产物：
  描述：

  (E)-N-(2-butenyl)aniline 、 2-溴苯乙酮 以 二氯甲烷 为溶剂， 以80%的产率得到N-(2-trans-Butenyl)-N-phenyl-1-amino-2-acetophenone
  参考文献：
  名称：

  Stereochemistry. 82. Conformation of fused five-membered heterocyclic rings derived from the intramolecular oxime olefin cycloaddition reaction

  摘要：

  Thermal intramolecular oxime olefin cycloaddition Of alpha-allylamino aldoximes and ketoximes 4 led stereospecifically to formation of oxadiazabicyclo[3.3.0]octanes 6. The presence of heteroatoms in these bicyclic fused 5-membered rings permits for the first time an evaluation of the conformation of this system by means of NMR. We found that some substituents in 6 restrict the conformational mobility of these five-membered rings to the extent that only one conformer was detected at 20-degrees-C. In other cases an equilibrium between two major conformers was revealed by NMR. Equilibrium measurements indicated a free energy of conversion of 13.2-13.4 kcal/mol, apparently a manifestation of the N-inversion in the isoxazolidine ring. NMR studies also showed that the NH-proton in isoxazolidines 6 prefers an axial orientation. Empirical force field data were adjusted for MM calculations in these bicyclic heterocycles. The MM2 force field with AMBER charge gave the best fit between calculated and experimental coupling constants.

  DOI：

  10.1021/jo00069a011