6,8-dimethoxy-7-(bromomethyl)-3,4-dihydro-1H-isochromen-1-one | 1294010-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,8-dimethoxy-7-(bromomethyl)-3,4-dihydro-1H-isochromen-1-one
• 英文别名: 7-bromomethyldihydroisocoumarin；7-(Bromomethyl)-6,8-dimethoxy-3,4-dihydroisochromen-1-one
• CAS: 1294010-19-7
• 化学式: C₁₂H₁₃BrO₄
• 分子量: 301.137
• InChiKey: NKHDIGPSZBNQCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,8-dimethoxy-7-(bromomethyl)-3,4-dihydro-1H-isochromen-1-one 在 水 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以77%的产率得到7-(hydroxymethyl)-6,8-dimethoxy-3,4-dihydro-1H-isochromen-1-one
  参考文献：
  名称：

  Total synthesis and cytotoxic activity of stellatin

  摘要：

  Stellatin (3,4-dihydro-8-hydroxy-7-hydroxymethyl-6-methoxyisocoumarin) (8), an extrolite of fungal genera Emericella and Aspergillus, was synthesized. Thus, Vilsmeier-Haack formylation of methyl ester of 3,5-dimethoxy-4-methylphenylacetic acid (1) to afford the formyl ester (2) followed sulfamic acid-sodium chlorite oxidation of the aldehydic function to yield the carboxy ester (3). Chemoselective reduction of ester function in the latter using NaBH4/THF/MeOH furnished the corresponding hydroxy acid (4) that on cyclodehydration afforded the 3,4-dihydro-6,8-dimethoxy-7-methylisocoumarin (5). Benzylic bromination of the C-7 methyl in 5 using NBS/benzoyl peroxide to give the 7-bromomethyldihydroisocoumarin (6) followed the nucleophilic substitution using aqueous acetone to provide 7-hydroxymethyl-dihydroisocoumarin (7). Finally, the regioselective demethylation of 8-methoxyl group using anhydrous magnesium iodide furnished the stellatin (8). The dihydroisocoumarins (5-8) were screened for cytotoxic activity against human keratinocyte cell line and were found to exhibit moderate to good activity.

  DOI：

  10.1080/10286020.2010.544654
• 作为产物：
  描述：

  <3,5-Dimethoxy-4-methyl-phenyl>-essigsaeure 在 甲醇 、 sodium chlorite 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 氨基磺酸 、 乙酸酐 、 三氯氧磷 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 二甲基亚砜 为溶剂， 反应 15.33h， 生成 6,8-dimethoxy-7-(bromomethyl)-3,4-dihydro-1H-isochromen-1-one
  参考文献：
  名称：

  Total synthesis and cytotoxic activity of stellatin

  摘要：

  Stellatin (3,4-dihydro-8-hydroxy-7-hydroxymethyl-6-methoxyisocoumarin) (8), an extrolite of fungal genera Emericella and Aspergillus, was synthesized. Thus, Vilsmeier-Haack formylation of methyl ester of 3,5-dimethoxy-4-methylphenylacetic acid (1) to afford the formyl ester (2) followed sulfamic acid-sodium chlorite oxidation of the aldehydic function to yield the carboxy ester (3). Chemoselective reduction of ester function in the latter using NaBH4/THF/MeOH furnished the corresponding hydroxy acid (4) that on cyclodehydration afforded the 3,4-dihydro-6,8-dimethoxy-7-methylisocoumarin (5). Benzylic bromination of the C-7 methyl in 5 using NBS/benzoyl peroxide to give the 7-bromomethyldihydroisocoumarin (6) followed the nucleophilic substitution using aqueous acetone to provide 7-hydroxymethyl-dihydroisocoumarin (7). Finally, the regioselective demethylation of 8-methoxyl group using anhydrous magnesium iodide furnished the stellatin (8). The dihydroisocoumarins (5-8) were screened for cytotoxic activity against human keratinocyte cell line and were found to exhibit moderate to good activity.

  DOI：

  10.1080/10286020.2010.544654

文献信息

• Total synthesis and cytotoxic activity of stellatin
  作者：Aamer Saeed、Zaman Ashraf、Hummera Rafique

  DOI：10.1080/10286020.2010.544654

  日期：2011.2

  Stellatin (3,4-dihydro-8-hydroxy-7-hydroxymethyl-6-methoxyisocoumarin) (8), an extrolite of fungal genera Emericella and Aspergillus, was synthesized. Thus, Vilsmeier-Haack formylation of methyl ester of 3,5-dimethoxy-4-methylphenylacetic acid (1) to afford the formyl ester (2) followed sulfamic acid-sodium chlorite oxidation of the aldehydic function to yield the carboxy ester (3). Chemoselective reduction of ester function in the latter using NaBH4/THF/MeOH furnished the corresponding hydroxy acid (4) that on cyclodehydration afforded the 3,4-dihydro-6,8-dimethoxy-7-methylisocoumarin (5). Benzylic bromination of the C-7 methyl in 5 using NBS/benzoyl peroxide to give the 7-bromomethyldihydroisocoumarin (6) followed the nucleophilic substitution using aqueous acetone to provide 7-hydroxymethyl-dihydroisocoumarin (7). Finally, the regioselective demethylation of 8-methoxyl group using anhydrous magnesium iodide furnished the stellatin (8). The dihydroisocoumarins (5-8) were screened for cytotoxic activity against human keratinocyte cell line and were found to exhibit moderate to good activity.