stellatin | 1083201-12-0

• 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: stellatin
• 英文别名: Stellatin (C11)；8-hydroxy-7-(hydroxymethyl)-6-methoxy-3,4-dihydroisochromen-1-one
• CAS: 1083201-12-0
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: BIWNDHPZHWCUSL-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  537.5±50.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  stellatin 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以55 mg的产率得到dihydroisocoumarin aldehyde
  参考文献：
  名称：

  A chromane derivative related to stellatin, and an α,-pyrone derivative from Emericella heterothallica

  摘要：

  DOI：

  10.1016/s0031-9422(00)97789-6
• 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 、 水 、 碘 、 乙酸酐 、 magnesium 、 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 、 丙酮 、 苯 为溶剂， 反应 16.83h， 生成 stellatin
  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.
• A chromane derivative related to stellatin, and an α,-pyrone derivative from Emericella heterothallica
  作者：Nobuo Kawahara、Shoichi Nakajima、Ken-Ichi Kawai

  DOI：10.1016/s0031-9422(00)97789-6

  日期：——