6,7-dimethoxy-N-(2,4,6-trimethylbenzoyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid | 206118-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6,7-dimethoxy-N-(2,4,6-trimethylbenzoyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
• 英文别名: 6,7-dimethoxy-2-(2,4,6-trimethylbenzoyl)-3,4-dihydro-1H-isoquinoline-1-carboxylic acid
• CAS: 206118-01-6
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: WXPLXMTWQYIESV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟乙酸酐 、 6,7-dimethoxy-N-(2,4,6-trimethylbenzoyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以55%的产率得到1-[6,7-dimethoxy-2-(2,4,6-trimethylbenzoyl)-3,4-dihydro-1H-isoquinolin-1-yl]-2,2,2-trifluoroethanone
  参考文献：
  名称：

  The Dakin-West Reaction of N-Acyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acids Using Trifluoroacetic Anhydride: Structural Revision for the Unexpected Product

  摘要：

  The Dakin-West reaction of N-pivaloyl- and N-benzoyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids (1 a-e) with trifluoroacetic anhydride yielded unexpectedly 1-(1-acyloxy-2,2,2-trifluoroethyl)-3,4-dihydroisoquinoline derivatives (3a-e) in good yields. Among of the products (3), the structure of 3 b has been confirmed by X-Ray crystallography. The carbamate derivatives (1h, i) gave 1-trifluoroacetyl-N-acyl-1,2,3,4-tetrahydroisoquinolines (4e, f), the Dakin-West reaction products, as a main product. The reaction of N-acetyl derivative (1 g) produced completely different type of the product (5).

  DOI：

  10.3987/com-97-8053
• 作为产物：
  描述：

  6,7-二甲氧基-1,2,3,4-四氢-异喹啉-1-羧酸乙酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 6,7-dimethoxy-N-(2,4,6-trimethylbenzoyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
  参考文献：
  名称：

  The Dakin-West Reaction of N-Acyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acids Using Trifluoroacetic Anhydride: Structural Revision for the Unexpected Product

  摘要：

  The Dakin-West reaction of N-pivaloyl- and N-benzoyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids (1 a-e) with trifluoroacetic anhydride yielded unexpectedly 1-(1-acyloxy-2,2,2-trifluoroethyl)-3,4-dihydroisoquinoline derivatives (3a-e) in good yields. Among of the products (3), the structure of 3 b has been confirmed by X-Ray crystallography. The carbamate derivatives (1h, i) gave 1-trifluoroacetyl-N-acyl-1,2,3,4-tetrahydroisoquinolines (4e, f), the Dakin-West reaction products, as a main product. The reaction of N-acetyl derivative (1 g) produced completely different type of the product (5).

  DOI：

  10.3987/com-97-8053