1-acetyl-3-chloro-2-methyl-2H-isoindole | 1285620-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1-acetyl-3-chloro-2-methyl-2H-isoindole
• 英文别名: 1-(3-Chloro-2-methylisoindol-1-yl)ethanone；1-(3-chloro-2-methylisoindol-1-yl)ethanone
• CAS: 1285620-96-3
• 化学式: C₁₁H₁₀ClNO
• 分子量: 207.659
• InChiKey: ZOZPJJBGPNBTLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-acetyl-3-chloro-2-methyl-2H-isoindole 、 4-甲苯硫酚 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以98%的产率得到1-acetyl-2-methyl-3-[(4-methylphenyl)sulfanyl]-2H-isoindole
  参考文献：
  名称：

  Nucleophilic substitutions in the isoindole series as a valuable tool to synthesize derivatives with antitumor activity

  摘要：

  A novel synthetic approach to the synthesis of 3-substituted isoindoles through nucleophilic substitution of 3-halo derivatives by charged carbon, and neutral nitrogen, oxygen, and sulfur nucleophiles, assisted by a 1-acyl group, is reported. Aryl-thio-isoindoles, obtained through a direct nucleophilic substitution with sulfur nucleophiles, showed cytotoxic activity, with GI(50) values from micromolar to sub-micromolar concentrations, against the total number of cell lines investigated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.056
• 作为产物：
  描述：

  异吲哚啉-1-酮 在 水 、 potassium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 23.0h， 生成 1-acetyl-3-chloro-2-methyl-2H-isoindole
  参考文献：
  名称：

  Nucleophilic substitutions in the isoindole series as a valuable tool to synthesize derivatives with antitumor activity

  摘要：

  A novel synthetic approach to the synthesis of 3-substituted isoindoles through nucleophilic substitution of 3-halo derivatives by charged carbon, and neutral nitrogen, oxygen, and sulfur nucleophiles, assisted by a 1-acyl group, is reported. Aryl-thio-isoindoles, obtained through a direct nucleophilic substitution with sulfur nucleophiles, showed cytotoxic activity, with GI(50) values from micromolar to sub-micromolar concentrations, against the total number of cell lines investigated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.056