4-acetyl-2-benzyl-2H-isoquinolin-1-one | 87275-04-5

• 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
• 英文名称: 4-acetyl-2-benzyl-2H-isoquinolin-1-one
• 英文别名: 4-acetyl-2-benzylisoquinolin-1-one
• CAS: 87275-04-5
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: JSHJMJXYHHEGIV-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159 °C(Solv: benzene (71-43-2))
• 沸点：
  502.7±50.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-benzyl-N-(2-bromobenzyl)amine 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 42.0h， 生成 4-acetyl-2-benzyl-2H-isoquinolin-1-one
  参考文献：
  名称：

  Intramolecular Pd-Mediated Processes of Amino-Tethered Aryl Halides and Ketones:  Insight into the Ketone α-Arylation and Carbonyl-Addition Dichotomy. A New Class of Four-Membered Azapalladacycles

  摘要：

  An exploration of the scope and limitations of Pd(0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from omega-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while (omega-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.

  DOI：

  10.1021/ja029114w

文献信息

• 1(2H)-isoquinolones as potential antiallergic agents.
  作者：MASAYASU KIMURA、ISAMI WAKI、YOJI DEGUCHI、KOUJI AMEMIYA、TETSUYA MAEDA

  DOI：10.1248/cpb.31.1277

  日期：——

  A series of 1 (2H)-isoquinolones was prepared by reaction of 4-acylisocoumarins with ammonium carbonate or primary amines in acetic acid. These compounds, after a 15-min pretreatment, inhibited histamine release from isolated rat mast cells, and some of them were potent when tested on rat passive cutaneous anaphylaxis (PCA assay 3 h after i. p. injection). The activities of these compounds were, however, lower than that of the already known 4-(4-carboxybenzoyl) isocoumarin.

  通过 4-酰基异香豆素与碳酸铵或伯胺在乙酸中的反应，制备了一系列 1 (2H)-异喹诺酮类化合物。这些化合物经过 15 分钟的预处理后，可抑制离体大鼠肥大细胞释放组胺。不过，这些化合物的活性低于已知的 4-（4-羧基苯甲酰基）异香豆素。
• KIMURA, MASAYASU;WAKI, ISAMI;DEGUCHI, YOJI;AMEMIYA, KOUJI;MAEDA, TETSUYA, CHEM. AND PHARM. BULL., 1983, 31, N 4, 1277-1282
  作者：KIMURA, MASAYASU、WAKI, ISAMI、DEGUCHI, YOJI、AMEMIYA, KOUJI、MAEDA, TETSUYA

  DOI：——

  日期：——