2-(4-氯苯甲酰基)-3,4-二氢-1H-异喹啉-1-羧酸 | 144149-81-5

• 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
• 中文名称: 2-(4-氯苯甲酰基)-3,4-二氢-1H-异喹啉-1-羧酸
• 英文名称: N-(4-chlorobenzoyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
• 英文别名: 1-Isoquinolinecarboxylic acid, 2-(4-chlorobenzoyl)-1,2,3,4-tetrahydro-；2-(4-chlorobenzoyl)-3,4-dihydro-1H-isoquinoline-1-carboxylic acid
• CAS: 144149-81-5
• 化学式: C₁₇H₁₄ClNO₃
• 分子量: 315.756
• InChiKey: XMYUBFNEEBDURU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-氯苯甲酰基)-3,4-二氢-1H-异喹啉-1-羧酸 、 三氟乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以58%的产率得到4-Chloro-benzoic acid 1-(3,4-dihydro-isoquinolin-1-yl)-2,2,2-trifluoro-ethyl ester
  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：

  1,2,3,4-四氢异喹啉-1-羧酸 、 4-氯苯甲酰氯 生成 2-(4-氯苯甲酰基)-3,4-二氢-1H-异喹啉-1-羧酸
  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

文献信息

• Unusual ring expansion observed during the Dakin–West reaction of tetrahydroisoquinoline-1-carboxylic acids using trifluoroacetic anhydride: an expedient synthesis of 3-benzazepine derivatives bearing a trifluoromethyl group
  作者：Masami Kawase

  DOI：10.1039/c39920001076

  日期：——

  The reaction of N-acyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids with trifluoroacetic anhydride proceeds through mesoionic 1,3-oxazol-5-one intermediates followed by ring expansion to form 2-trifluoromethyltetrahydro-3-benzazepinone derivatives in good yields.

  N-酰基-1,2,3,4-四氢异喹啉-1-羧酸与三氟乙酸酐通过介离子1,3-恶唑-5-酮中间体反应，然后扩环生成2-三氟甲基四氢-3-苯并氮杂酮衍生品收益率良好。
• The Dakin-West Reaction of N-Acyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acids Using Trifluoroacetic Anhydride: Structural Revision for the Unexpected Product
  作者：Masami Kawase、Youichi Okada、Hiroshi Miyamae

  DOI：10.3987/com-97-8053

  日期：——

  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).