1-(diphenylmethylen)-4,4-dimethyl-2,3,4,5-tetrahydro-benzo[d]azepinium triflate | 1410788-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1-(diphenylmethylen)-4,4-dimethyl-2,3,4,5-tetrahydro-benzo[d]azepinium triflate
• 英文别名: 5-benzhydrylidene-2,2-dimethyl-3,4-dihydro-1H-3-benzazepin-3-ium;trifluoromethanesulfonate
• CAS: 1410788-28-1
• 化学式: CHF₃O₃S*C₂₅H₂₅N
• 分子量: 489.559
• InChiKey: RQMFNYJQJRLYBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [Pd₂(C,N-C₆H₄CH₂CMe₂NH₂-2)₂(μ-Cl)₂] 、 1,1'-(1,1-丙二烯二基)二苯 、 三氟甲磺酸铊 以 丙酮 、 四氢呋喃 为溶剂， 反应 12.5h， 以61%的产率得到1-(diphenylmethylen)-4,4-dimethyl-2,3,4,5-tetrahydro-benzo[d]azepinium triflate
  参考文献：
  名称：

  Insertion of Allenes into the Pd–C Bond of Ortho-Palladated Primary Arylamines of Biological Relevance: Phenethylamine, Phentermine, (l)-Phenylalanine Methyl Ester, and (l)-Tryptophan Methyl Ester. Synthesis of Tetrahydro-3-benzazepines and Their Salts

  摘要：

  The previously reported ortho-metalated complexes [Pd(C,N-ArCH2CRR'NH2-2)(mu-X)](2) derived from phenethylamine (Ar = C6H4, R = R' = H, X = Cl, Br), phentermine (Ar = C6H4, R = R' = Me, X = Cl), (L)-phenylalanine methyl ester (Ar = C6H4, R = H, R' = CO2Me, X = Cl, Br)), and (L)-tryptophan methyl ester (Ar = C8H5N, R = H, R' = CO2Me, X = Cl) react with various allenes to give (1) the corresponding eta(3)-allyl complexes derived from the insertion of one molecule of the allene into the Pd-C bond, the formation of which has been studied by DFT using a model complex, or (2) Pd(0) and the tetrahydro-3-benzazepinium salts, resulting from the decomposition of the above mentioned eta(3)-allyl complexes, containing an exocyclic double bond, which, subsequently, react with a base to afford the corresponding benzazepines. The regiochemistry of these decomposition reactions has been studied and compared wit:a that described for similar processes involving five-membered palladacycles. The crystal structures of the salts of some benzazepines and one isoquinoline, derived from a five-membered palladacycle, have been determined by X-ray diffraction studies.

  DOI：

  10.1021/om300928j