3,3-dimethyl-4-methylen-6-methoxy-1,2,3,4-tetrahydroisoquinolinium bromide | 1410788-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 3,3-dimethyl-4-methylen-6-methoxy-1,2,3,4-tetrahydroisoquinolinium bromide
• 英文别名: 6-Methoxy-3,3-dimethyl-4-methylidene-1,2-dihydroisoquinolin-2-ium;bromide
• CAS: 1410788-52-1
• 化学式: BrH*C₁₃H₁₇NO
• 分子量: 284.196
• InChiKey: RACVHEVZEALGKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.43
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基-1,2-丁二烯 、 [Pd₂{κ²(C,N)-C₆H₄CH₂NH₂-2,OMe-5}₂(μ-Br)₂] 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到3,3-dimethyl-4-methylen-6-methoxy-1,2,3,4-tetrahydroisoquinolinium bromide
  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