7-amino-1-methyl-3,4-dihydroisoquinoline | 213765-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-amino-1-methyl-3,4-dihydroisoquinoline
• 英文别名: (+/-) 7-Amino-1-methyl-3,4-dihydroisoquinoline；1-methyl-3,4-dihydroisoquinolin-7-amine
• CAS: 213765-85-6
• 化学式: C₁₀H₁₂N₂
• 分子量: 160.219
• InChiKey: JBXUYMPSEDWNSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-amino-1-methyl-3,4-dihydroisoquinoline 以 四氢呋喃 、 丙酮 为溶剂， 生成 7-amino-1,1,2-trimethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  PREPARATION OF 1,7-DISUBSTITUTED-1,2,3,4-TETRAHYDROISOQUINOLINES

  摘要：

  A simple procedure for the preparation of 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines from 3,4-dihydroisoquinoline (2) is presented. This strategy overcomes the limitation of cyclisation approaches which generally require electron rich ring systems. A variety of 1-substituents has been incorporated using the appropriate organometallic or activated methylene nucleophile to prepare both electron rich (7a-f) and electron deficient 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines (16, 17).

  DOI：

  10.1081/scc-120005939
• 作为产物：
  描述：

  1-甲基-3,4-二氢异喹啉 在 盐酸 、 硫酸 、 potassium nitrate 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 生成 7-amino-1-methyl-3,4-dihydroisoquinoline
  参考文献：
  名称：

  PREPARATION OF 1,7-DISUBSTITUTED-1,2,3,4-TETRAHYDROISOQUINOLINES

  摘要：

  A simple procedure for the preparation of 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines from 3,4-dihydroisoquinoline (2) is presented. This strategy overcomes the limitation of cyclisation approaches which generally require electron rich ring systems. A variety of 1-substituents has been incorporated using the appropriate organometallic or activated methylene nucleophile to prepare both electron rich (7a-f) and electron deficient 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines (16, 17).

  DOI：

  10.1081/scc-120005939

文献信息

• Anti-convulsant isoquinolyl-benzamide derivatives
  申请人：SmithKline Beecham, p.l.c.

  公开号：US06277861B1

  公开（公告）日：2001-08-21

  Compounds of formula (I) and pharmaceutically acceptable salts thereof, where R1 is hydrogen, C1-6alkyl (optionally substituted by hydroxy or C1-4alkoxy), C1-6alkenyl, C1-6alkynyl, C1-6alkylCO—, formyl, CF3CO— or C1-6alkylSO2—; R2 is hydrogen or up to three substituents selected from halogen, NO2, CN, N3, CF3O—, CF3S—, CF3CO—, trifluoromethyldiazirinyl, C 1-6?alkyl, C1-6alkenyl, C1-6alkynyl, C1-6perfluoroalkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl-, C1-6alkylO—, C1-6alkylCO—, C3-6cycloalkylO—, C3-6cycloalkylCO—, C3-6cycloalkyl-C1-4alkylO—, C3-6cycloalkyl-C1-4alkylCO—, phenyl, phenoxy, benzyloxy, benzoyl, phenyl-C1-4alkyl-, C1-6alkylS—, C1-6alkylSO2—, (C1-4alkyl)2NSO2—, (C1-4alkyl)NHSO2—, (C1-4alkyl)2NCO—, (C1-4alkyl)NHCO— or CONH2; or —NR5R6 where R5 is hydrogen or C1-4alkyl, and R6 is hydrogen, C1-4alkyl, formyl, —CO2C1-4alkyl or —COC1-4alkyl; or two R2 groups together form a carbocyclic ring that is saturated or unsaturated and unsubstituted or substituted by —OH or ═O; and the two R3 groups and the two R4 groups are each independently hydrogen or C1-6alkyl or the two R3 groups and/or the two R4 groups together form a C3-6spiroalkyl group provided that at least one R3 and R4 group is not hydrogen, are useful in the treatment and prophylaxis of epilepsy and other disorders.

  式(I)的化合物及其药学上可接受的盐，其中R1是氢、C1-6烷基（可选地被羟基或C1-4烷氧基取代）、C1-6烯基、C1-6炔基、C1-6烷基CO-、甲酰基、CF3CO-或C1-6烷基SO2-；R2是氢或最多三个取代基，所选自卤素、NO2、CN、N3、CF3O-、CF3S-、CF3CO-、三氟甲基重氮基、C1-6烷基、C1-6烯基、C1-6炔基、C1-6全氟烷基、C3-6环烷基、C3-6环烷基-C1-4烷基、C1-6烷氧基、C1-6烷基CO-、C3-6环烷基氧基、C3-6环烷基CO-、C3-6环烷基-C1-4烷氧基、C3-6环烷基-C1-4烷基CO-、苯基、苯氧基、苄氧基、苯甲酰基、苯基-C1-4烷基、C1-6烷基S-、C1-6烷基SO2-、（C1-4烷基）2NSO2-、（C1-4烷基）NHSO2-、（C1-4烷基）2NCO-、（C1-4烷基）NHCO-或CONH2；或-NR5R6，其中R5是氢或C1-4烷基，R6是氢、C1-4烷基、甲酰基、-CO2C1-4烷基或-COC1-4烷基；或两个R2基共同形成一个碳环，该碳环饱和或不饱和，未取代或被-OH或═O取代；两个R3基和两个R4基各自独立地是氢或C1-6烷基，或两个R3基和/或两个R4基共同形成一个C3-6螺环烷基，前提是至少一个R3和R4基不是氢，可用于治疗和预防癫痫和其他疾病。
• ANTI-CONVULSANT ISOQUINOLYL-BENZAMIDE DERIVATIVES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0971897A1

  公开（公告）日：2000-01-19
• US6277861B1
  申请人：——

  公开号：US6277861B1

  公开（公告）日：2001-08-21
• [EN] ANTI-CONVULSANT ISOQUINOLYL-BENZAMIDE DERIVATIVES<br/>[FR] DERIVES ANTICONVULSIVANTS D'ISOQUINOLYL-BENZAMIDE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1998041507A1

  公开（公告）日：1998-09-24

  (EN) Compounds of formula (I) and pharmaceutically acceptable salts thereof, where R1 is hydrogen, C1-6alkyl (optionally substituted by hydroxy or C1-4alkoxy), C1-6alkenyl, C1-6alkynyl, C1-6alkylCO-, formyl, CF3CO- or C1-6alkylSO2-; R2 is hydrogen or up to three substituents selected from halogen, NO2, CN, N3, CF3O-, CF3S-, CF3CO-, trifluoromethyldiazirinyl, C1 -6alkyl, C1-6alkenyl, C1-6alkynyl, C1-6perfluoroalkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl-, C1-6alkylO-, C1-6alkylCO-, C3-6cycloalkylO-, C3-6cycloalkylCO-, C3-6cycloalkyl-C1-4alkylO-, C3-6cycloalkyl-C1-4alkylCO-, phenyl, phenoxy, benzyloxy, benzoyl, phenyl-C1-4alkyl-, C1-6alkylS-, C1-6alkylSO2-, (C1-4alkyl)2NSO2-, (C1-4alkyl)NHSO2-, (C1-4alkyl)2NCO-, (C1-4alkyl)NHCO- or CONH2; or -NR5R6 where R5 is hydrogen or C1-4alkyl, and R6 is hydrogen, C1-4alkyl, formyl, -CO2C1-4alkyl or -COC1-4alkyl; or two R2 groups together form a carbocyclic ring that is saturated or unsaturated and unsubstituted or substituted by -OH or =O; and the two R3 groups and the two R4 groups are each independently hydrogen or C1-6alkyl or the two R3 groups and/or the two R4 groups together form a C3-6spiroalkyl group provided that at least one R3 and R4 group is not hydrogen, are useful in the treatment and prophylaxis of epilepsy and other disorders.(FR) Composés de la formule (I) et sels pharmaceutiquement acceptables de ces composés. Dans cette formule, R1 représente de l'hydrogène, un C1-6alkyle (éventuellement substitué par un hydroxy ou un C1-4alkoxy), un C1-6alcényle, un C1-6alkynyle, un C1-6alkylCO-, un formyle, un CF3CO- ou un C1-6alkylSO2-; R2 représente de l'hydrogène ou jusqu'à trois substituants sélectionnés à partir d'un halogène, de NO2, CN, N3, CF3O-, CF3S-, CF3CO-, de trifluorométhyldiazirinyle, C1-6alkyle, C1-6alcényle, C1-6alkynyle, C1-6perfluoroalkyle, C3-6cycloalkyle, C3-6cycloalkyl-C1-4alkyl, C1-6alkylO-, C1-6alkylCO-, C3-6cycloalkylO-, C3-6cycloalkylCO-, C3-6cycloalkyl-C1-4alkylO-, C3-6cycloalkyl-C1-4alkylCO-, phényle, phénoxy, benzyloxy, benzoyle, phényl-C1-4alkyl-, C1-6alkylS-, C1-6alkylSO2-, (C1-4alkyl)2NSO2-, (C1-4alkyl)NHSO2-, (C1-4alkyl)2NCO-, (C1-4alkyl)NHCO- ou CONH2; ou bien -NR5R6 où R5 représente de l'hydrogène ou C1-4alkyl et R6 représente de l'hydrogène, C1-4alkyle, formyle, -CO2C1-4alkyl ou -COC1-4-alkyle; ou bien deux groupes R2 forment ensemble un noyau carbocyclique qui est saturé ou non et substitué ou non par -OH ou =OH, et les deux groupes R3 et les deux groupes R4 représentent chacun indépendamment de l'hydrogène ou un C1-6alkyle ou bien les deux groupes R3 et/ou les deux groupes R4 forment ensemble un groupe C3-6spiroalkyle à condition qu'au moins un groupe R3 et R4 ne représente pas de l'hydrogène. Ces composés sont utilisés dans le traitement et la prophylaxie de l'épilepsie et d'autres troubles.
• PREPARATION OF 1,7-DISUBSTITUTED-1,2,3,4-TETRAHYDROISOQUINOLINES
  作者：Jag P. Heer、John D. Harling、Mervyn Thompson

  DOI：10.1081/scc-120005939

  日期：2002.1

  A simple procedure for the preparation of 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines from 3,4-dihydroisoquinoline (2) is presented. This strategy overcomes the limitation of cyclisation approaches which generally require electron rich ring systems. A variety of 1-substituents has been incorporated using the appropriate organometallic or activated methylene nucleophile to prepare both electron rich (7a-f) and electron deficient 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines (16, 17).