N-methyl-6',7'-dimethoxy-2',3'-dihydro-1'H-spiro[cyclopentan-1,4'-isoquinoline]-1'-carboxamide | 329965-88-0

• 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: N-methyl-6',7'-dimethoxy-2',3'-dihydro-1'H-spiro[cyclopentan-1,4'-isoquinoline]-1'-carboxamide
• 英文别名: 6',7'-dimethoxy-N-methyl-2',3'-dihydro-1'H-spiro[cyclopentane-1,4'-isoquinoline]-1'-carboxamide；6,7-dimethoxy-4-spirocyclopentane-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid N-methylamide；6,7-dimethoxy-N-methylspiro[2,3-dihydro-1H-isoquinoline-4,1'-cyclopentane]-1-carboxamide
• CAS: 329965-88-0
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: RWMSWBMYEASOIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-6',7'-dimethoxy-2',3'-dihydro-1'H-spiro[cyclopentan-1,4'-isoquinoline]-1'-carboxamide 在 吡啶 、 potassium iodide 作用下， 以 1,4-二氧六环 、 乙醇 、 苯 为溶剂， 生成 N-methyl-6',7'-dimethoxy-2'-[2-(diethylamino)-acetyl]-2',3'-dihydro-1'H-spiro[cyclopentane-1,4'-isoquinoline]-1'-carboxamide
  参考文献：
  名称：

  Synthesis of new 2-substituted 6,7-dimethoxy-1-(methylcarbamoyl)-4-spirocyclopentane-1,2,3,4-tetrahydroisoquinolines

  摘要：

  New 2-(heterylmethyl) derivatives were synthesized from 6,7-dimethoxy-4-spirocyclopentane-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid N-methylamide and heterylmethyl chlorides. The reactions of 2-chloroacetyl-substituted tetrahydroisoquinoline with versatile secondary amines and heterylthiols afforded the corresponding 2-aminoacetyl and 2-(heterylsulfanylacetyl) derivatives of tetrahydroisoquinoline series.

  DOI：

  10.1134/s1070428013110122
• 作为产物：
  描述：

  6,7-dimethoxy-4-spirocyclopentane-3,4-dihydroisoquinoline-1-carboxylic acid N-methylamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以66.2%的产率得到N-methyl-6',7'-dimethoxy-2',3'-dihydro-1'H-spiro[cyclopentan-1,4'-isoquinoline]-1'-carboxamide
  参考文献：
  名称：

  Synthesis of novel 1,2-functionally-substituted 6,7-dimethoxy-4-spirocyclo-pentanetetrahydroisoquinolines

  摘要：

  1-[( 3,4-Dimethoxyphenyl)cyclopentyl] methylamine has been used in the synthesis of 6,7-dimethoxy4- spirocyclopentane-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid N-methylamide which is employed in the preparation of novel derivatives with substituents in positions 1,2,6, and 7.

  DOI：

  10.1007/s10593-009-0385-5

文献信息

• Synthesis of New 2′-(2- and 3-Aminopropanoyl)-6′,7′-dimethoxy-2′,3′-dihydro-1′H-spiro[cyclopentane-1,4′-isoquinoline]-1′-carboxamides
  作者：A. A. Aghekyan、G. G. Mkryan、H. A. Panosyan

  DOI：10.1134/s1070428019030047

  日期：2019.3

  6,7-Dimethoxy-N-methyl-2,3-dihydro-1H-spiro[cyclopentane-1,4-isoquinoline]-1-carboxamide reacted with 2-bromopropanoyl chloride to give the corresponding 2-bromopropanamide which was converted to substituted 2-aminopropanoyl derivatives via reactions with cyclic secondary amines. The reaction of 6,7-dimethoxy-N-methyl-2,3-dihydro-1H-spiro[cyclopentane-1,4-isoquinoline]-1-carboxamide with acryloyl chloride, followed by treatment of the resulting acrylamide with amines, afforded 3-aminopropanoyl derivatives.
• Synthesis of 2-propanol derivatives of N-methyl-6′,7′-dimethoxy-2′,3′-dihydro-1′H-spiro[cyclopentan-1,4′-isoquinoline]-1′-carboxamide
  作者：A. A. Aghekyan、G. G. Mkryan、O. S. Noravyan、T. O. Asatryan、R. E. Muradyan、G. A. Panosyan

  DOI：10.1134/s1070428015020153

  日期：2015.2

  Reaction of N-methyl-6',7'-dimethoxy-2',3'-dihydro-1'H-spiro[cyclopentan-1,4'-isoquinoline]-1'-carboxamide with phenoxymethyloxiranes substituted in the aromatic ring afforded new propanediol derivatives, and from the epoxy derivative of the same tetrahydroisoquinoline and secondary amines the corresponding aminopropanols of the tetrahydroisoquinoline series were prepared.
• Synthesis of new 2-substituted 6,7-dimethoxy-1-(methylcarbamoyl)-4-spirocyclopentane-1,2,3,4-tetrahydroisoquinolines
  作者：A. A. Aghekyan、G. G. Mkryan、E. A. Markaryan

  DOI：10.1134/s1070428013110122

  日期：2013.11

  New 2-(heterylmethyl) derivatives were synthesized from 6,7-dimethoxy-4-spirocyclopentane-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid N-methylamide and heterylmethyl chlorides. The reactions of 2-chloroacetyl-substituted tetrahydroisoquinoline with versatile secondary amines and heterylthiols afforded the corresponding 2-aminoacetyl and 2-(heterylsulfanylacetyl) derivatives of tetrahydroisoquinoline series.
• Synthesis of novel 1,2-functionally-substituted 6,7-dimethoxy-4-spirocyclo-pentanetetrahydroisoquinolines
  作者：A. A. Aghekyan、E. A. Arakelyan、G. A. Panosyan、A. G. Khachatryan、E. A. Markaryan

  DOI：10.1007/s10593-009-0385-5

  日期：2009.9

  1-[( 3,4-Dimethoxyphenyl)cyclopentyl] methylamine has been used in the synthesis of 6,7-dimethoxy4- spirocyclopentane-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid N-methylamide which is employed in the preparation of novel derivatives with substituents in positions 1,2,6, and 7.