N-(2-bromo-4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione | 500102-11-4

• 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-bromo-4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione
• 英文别名: 2-(2-Bromo-4-methylphenyl)isoquinoline-1,3(2H,4H)-dione；2-(2-bromo-4-methylphenyl)-4H-isoquinoline-1,3-dione
• CAS: 500102-11-4
• 化学式: C₁₆H₁₂BrNO₂
• 分子量: 330.181
• InChiKey: BWKUYZVFAFFROW-UHFFFAOYSA-N

物化性质

• 熔点：
  162-164 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  500.3±50.0 °C(Predicted)
• 密度：
  1.521±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 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-bromo-4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 7.0h， 以52%的产率得到3-methylbenzoxazolo[3,2-b]isoquinolin-11-one
  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：

  2-碘苯乙酸 在 氯化亚砜 、 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 20.25h， 生成 N-(2-bromo-4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione
  参考文献：
  名称：

  2-芳基乙酰胺可作为3-氨基异香豆素和高邻苯二甲酰亚胺衍生物的多功能前体：钯催化的级联双羰基化反应

  摘要：

  已经开发了通过钯催化的2-（2-碘代芳基）乙酰胺的羰基合成生物相关的邻苯二甲酰亚胺和3-氨基异香豆素核。起始酰胺底物上的N取代程度决定了是在催化循环的最后一步中发生C偶联还是C偶联，从而产生了每种类型的杂环。在起始乙酰胺中引入第二个C-卤素键可进行涉及CH-H活化步骤的催化级联双羰基化反应，从而生成稠合的杂环结构。

  DOI：

  10.1002/adsc.201600224

文献信息

• A new photochemical synthesis of benzoxazolo[3,2-b]isoquinolin-11-one and isoquinolino[3,2-b][1,3]benzoxazin-11-one
  作者：Annamalai Senthilvelan、Vayalakkavoor T. Ramakrishnan

  DOI：10.1016/s0040-4039(02)01955-x

  日期：2002.11

  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.
• 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.
• 2-Arylacetamides as Versatile Precursors for 3-Aminoisocoumarin and Homophthalimide Derivatives: Palladium-Catalyzed Cascade Double Carbonylation Reactions
  作者：Roberto Frutos-Pedreño、José-Antonio García-López

  DOI：10.1002/adsc.201600224

  日期：2016.8.18

  The synthesis of biologically relevant homophthalimide and 3‐aminoisocoumarin nuclei via palladium‐catalyzed carbonylation of 2‐(2‐iodoaryl)acetamides has been developed. The degree of N‐substitution on the starting amide substrate dictates whether C−N or C−O coupling takes place in the final step of the catalytic cycle giving rise to each type of heterocycle. The introduction of a second C−halogen

  已经开发了通过钯催化的2-（2-碘代芳基）乙酰胺的羰基合成生物相关的邻苯二甲酰亚胺和3-氨基异香豆素核。起始酰胺底物上的N取代程度决定了是在催化循环的最后一步中发生C偶联还是C偶联，从而产生了每种类型的杂环。在起始乙酰胺中引入第二个C-卤素键可进行涉及CH-H活化步骤的催化级联双羰基化反应，从而生成稠合的杂环结构。
• Photochemical synthesis of benzoxazolo[3,2-b]isoquinolin-11-one and isoquinolino[3,2-b][1,3]benzoxazin-11-one under basic conditions
  作者：A. Senthilvelan、D. Thirumalai、V.T. Ramakrishnan

  DOI：10.1016/j.tet.2005.02.068

  日期：2005.4

  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.