[5-Chloro-3-(3-hydroxypropyl)-2,7-dimethyl-6,8-dioxoisoquinolin-7-yl] butanoate | 900812-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂非酮类
• 英文名称: [5-Chloro-3-(3-hydroxypropyl)-2,7-dimethyl-6,8-dioxoisoquinolin-7-yl] butanoate
• CAS: 900812-33-1
• 化学式: C₁₈H₂₂ClNO₅
• 分子量: 367.829
• InChiKey: IOVPSHVHQLFEKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [5-Chloro-3-(3-hydroxypropyl)-2,7-dimethyl-6,8-dioxoisoquinolin-7-yl] butanoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 以46%的产率得到
  参考文献：
  名称：

  Bromoetherification-based strategy towards the spirocyclic chromophore of chlorofusin

  摘要：

  A short and direct route to the racemic model chromophore of the potent p53-MDM2 antagonist, chlorofusin, is presented. The spirocyclic chromophores were successfully constructed in high yields by an NBS-mediated intramolecular haloetherification. Ring expansion was observed in the subsequent reaction of the bromides with silver nitrate in refluxing acetone and water. Conversion of the bromides to the desired ketones was finally achieved by NMO oxidation. All four possible isomeric chromophores were finally synthesized and unambiguously characterized by X-ray crystallography studies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.062
• 作为产物：
  描述：

  acetic acid 5-(2-chloro-6-formyl-3,5-dihydroxy-4-methylphenyl)-4-oxopentyl ester 在 palladium(II) acetate 、 高氯酸 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 生成 [5-Chloro-3-(3-hydroxypropyl)-2,7-dimethyl-6,8-dioxoisoquinolin-7-yl] butanoate
  参考文献：
  名称：

  Bromoetherification-based strategy towards the spirocyclic chromophore of chlorofusin

  摘要：

  A short and direct route to the racemic model chromophore of the potent p53-MDM2 antagonist, chlorofusin, is presented. The spirocyclic chromophores were successfully constructed in high yields by an NBS-mediated intramolecular haloetherification. Ring expansion was observed in the subsequent reaction of the bromides with silver nitrate in refluxing acetone and water. Conversion of the bromides to the desired ketones was finally achieved by NMO oxidation. All four possible isomeric chromophores were finally synthesized and unambiguously characterized by X-ray crystallography studies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.062

文献信息

• Bromoetherification-based strategy towards the spirocyclic chromophore of chlorofusin
  作者：Wan-Guo Wei、Wen-Jian Qian、Yong-Xia Zhang、Zhu-Jun Yao

  DOI：10.1016/j.tetlet.2006.04.062

  日期：2006.6

  A short and direct route to the racemic model chromophore of the potent p53-MDM2 antagonist, chlorofusin, is presented. The spirocyclic chromophores were successfully constructed in high yields by an NBS-mediated intramolecular haloetherification. Ring expansion was observed in the subsequent reaction of the bromides with silver nitrate in refluxing acetone and water. Conversion of the bromides to the desired ketones was finally achieved by NMO oxidation. All four possible isomeric chromophores were finally synthesized and unambiguously characterized by X-ray crystallography studies. (c) 2006 Elsevier Ltd. All rights reserved.