(Z)-(S)-1-((ethoxycarbonyl)methyliden)-4-(carbomethoxy)-2,3,4,5-tetrahydro-benzo[d]azepine | 1410788-40-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-(S)-1-((ethoxycarbonyl)methyliden)-4-(carbomethoxy)-2,3,4,5-tetrahydro-benzo[d]azepine
• 英文别名: methyl (2S,5Z)-5-(2-ethoxy-2-oxoethylidene)-1,2,3,4-tetrahydro-3-benzazepine-2-carboxylate
• CAS: 1410788-40-7
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: UCEQJLOYLDJRHR-TZIYXEQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-(S)-1-((ethoxycarbonyl)methyliden)-4-(carbomethoxy)-2,3,4,5-tetrahydro-benzo[d]azepinium triflate 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (Z)-(S)-1-((ethoxycarbonyl)methyliden)-4-(carbomethoxy)-2,3,4,5-tetrahydro-benzo[d]azepine
  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

文献信息

• Insertion of Allenes into the Pd–C Bond of Ortho-Palladated Primary Arylamines of Biological Relevance: Phenethylamine, Phentermine, (<scp>l</scp>)-Phenylalanine Methyl Ester, and (<scp>l</scp>)-Tryptophan Methyl Ester. Synthesis of Tetrahydro-3-benzazepines and Their Salts
  作者：José-Antonio García-López、Isabel Saura-Llamas、John E. McGrady、Delia Bautista、José Vicente

  DOI：10.1021/om300928j

  日期：2012.12.10

  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.