N-Allyl-N-phenyl-1-amino-2-propanone | 150630-81-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-Allyl-N-phenyl-1-amino-2-propanone
• 英文别名: N-allyl-N-acetonylaniline；1-(N-prop-2-enylanilino)propan-2-one
• CAS: 150630-81-2
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: URGFIMNAMZPARC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Allyl-N-phenyl-1-amino-2-propanone 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以84%的产率得到N-Allyl-N-phenyl-1-amino-2-propanone (E/Z)-oxime
  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：

  N-烯丙基苯胺 、 溴丙酮 以 二氯甲烷 为溶剂， 反应 72.0h， 以70%的产率得到N-Allyl-N-phenyl-1-amino-2-propanone
  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

文献信息

• Development of a Method for the Reductive Cyclization of Enones by a Titanium Catalyst
  作者：Natasha M. Kablaoui、Stephen L. Buchwald

  DOI：10.1021/ja954192n

  日期：1996.1.1

  which bis(trimethylphosphine)titanocene is used to catalyze the reductive cyclization of enones to cyclopentanols via a metallacyclic intermediate has been developed. The key step in the process is the cleavage of the titanium−oxygen bond in the metallacycle by a silane to regenerate the catalyst. Mechanistic aspects of the reaction are discussed and the diastereoselectivity of the transformation is studied

  已经开发了一种有效的方案，其中双（三甲基膦）二茂钛用于通过金属环中间体催化烯酮还原环化为环戊醇。该过程的关键步骤是通过硅烷裂解金属环中的钛-氧键以再生催化剂。讨论了反应的机理方面，并使用非手性和手性底物研究了转化的非对映选择性。描述了该过程的范围和限制。还开发了用于生成空气和湿度敏感催化剂的原位协议。这项工作首次证明了使用早期过渡金属配合物催化烯烃与含杂原子官能团的还原环化的可行性。
• Reductive Cyclization of Enones by a Titanium Catalyst
  作者：Natasha M. Kablaoui、Stephen L. Buchwald

  DOI：10.1021/ja00130a021

  日期：1995.6
• Diastereoselective Synthesis of γ-Butyrolactones from Enones Mediated or Catalyzed by a Titanocene Complex
  作者：Natasha M. Kablaoui、Frederick A. Hicks、Stephen L. Buchwald

  DOI：10.1021/ja960953q

  日期：1996.1.1