(S)-1-(1-(trimethylsilyl)ethyliden)-4-(methoxycarbonyl)-2,3,4,5-tetrahydro-indolo[2,1-d]azepinium chloride | 1410788-22-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (S)-1-(1-(trimethylsilyl)ethyliden)-4-(methoxycarbonyl)-2,3,4,5-tetrahydro-indolo[2,1-d]azepinium chloride
• CAS: 1410788-22-5
• 化学式: C₁₉H₂₆N₂O₂Si*ClH
• 分子量: 378.974
• InChiKey: XBWNYADRRZZRIP-CIMGINCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54.12
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  盐酸 、 (S)-1-(1-(trimethylsilyl)ethyliden)-4-(methoxycarbonyl)-2,3,4,5-tetrahydro-indolo[2,1-d]azepinium chloride 、 水 以 氯仿 为溶剂， 反应 12.0h， 以78%的产率得到(Z)-(S)-1-(ethyliden)-4-(methoxycarbonyl)-2,3,4,5-tetrahydro-indolo[2,1-d]azepinium chloride monohydrate
  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
• 作为产物：
  描述：

  在 一氧化碳 作用下， 以 氯仿 为溶剂， 反应 7.0h， 以77%的产率得到(S)-1-(1-(trimethylsilyl)ethyliden)-4-(methoxycarbonyl)-2,3,4,5-tetrahydro-indolo[2,1-d]azepinium chloride
  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