N-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione | 407628-55-1

• 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: N-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione
• 英文别名: 2-[(2-chlorophenyl)methyl]-4H-isoquinoline-1,3-dione
• CAS: 407628-55-1
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: HPOSNEHKDXNNLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 15.0h， 以69%的产率得到N-(2-chlorobenzyl)-2-methylbenzamide
  参考文献：
  名称：

  A new photochemical synthesis of benzoxazolo[3,2-b]isoquinolin-11-one and isoquinolino[3,2-b][1,3]benzoxazin-11-one

  摘要：

  Photocyclization of substituted tetrahydroisoquinoline-1,3-diones, under base-mediated conditions, afforded benzoxazolo[3,2-b]isoquinotin-11-ones and an isoquinolino[3,2-b]benzoxazin-11-one. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01955-x
• 作为产物：
  描述：

  邻羧基苯乙酸 、 邻氯苯甲胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以71%的产率得到N-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione
  参考文献：
  名称：

  Photochemical synthesis of benzoxazolo[3,2-b]isoquinolin-11-one and isoquinolino[3,2-b][1,3]benzoxazin-11-one under basic conditions

  摘要：

  Irradiation of N-phenyl substituted isoquinolines in acetonitrile containing 1 M NaOH in a multilamp reactor (MLR) furnished benzoxazolo[3,2-b]isoquinolin-11-ones. In contrast, irradiation of the N-benzyl substituted isoquinoline derivative under the same conditions afforded the hydrolysed N-benzylbenzamide derivative. The isoquinolinobenzoxazine was obtained by irradiating the N-benzyl substituted isoquinoline derivative at higher basic conditions. The required isoquinolines were synthesized under solvent-free, solid supported microwave conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.068

文献信息

• Three tetrahydroisoquinolinedione derivatives
  作者：A. Subbiah Pandi、V. Rajakannan、D. Velmurugan、Masood Parvez、Moon-Jib Kim、A. Senthilvelan、S. Narasinga Rao

  DOI：10.1107/s0108270102000896

  日期：2002.3.15

  N-(2-Chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione, C16H12ClNO2, crystallizes in P2(1)/n with three crystallographically independent molecules in the asymmetric unit, which differ slightly in conformation, N-(2-bromo-4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione, C16H12BrNO2, crystallizes in P2(1)/n with one molecule in the asymmetric unit and N-(2,3-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione, C15H9Cl2NO2, crystallizes in P2(1)/c with one molecule in the asymmetric unit. In all three structures, the heterocyclic rings adopt approximately planar conformations. The pyridine rings are orthogonal to the substituted phenyl rings. In all three structures, the crystal packing is stabilized by intermolecular C-H....O hydrogen bonds.