juncusol dimethyl ether | 66447-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: juncusol dimethyl ether
• 英文别名: 2,7-Dimethoxy-1,6-dimethyl-5-vinyl-9,10-dihydrophenanthrene；5-ethenyl-2,7-dimethoxy-1,6-dimethyl-9,10-dihydrophenanthrene
• CAS: 66447-86-7
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: YQWDVVLBMPXIIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  juncusol dimethyl ether 以 苯 为溶剂， 反应 1.5h， 以200 mg的产率得到2,7-Dimethoxy-1,6-dimethyl-9,10,12,13-tetrahydropyrene
  参考文献：
  名称：

  Action of antialgal compounds fromJuncus effusus L. onSelenastrum capricornutum

  摘要：

  Twenty-nine free and glucosylated dihydrophenanthrenes and tetrahydropyrenes isolated from Juncus effusus have been tested against the unicellular green alga Selenastrum capricornutum. The free compounds showed a strong inhibitory activity, while the glucosides were inactive or had a slight stimulating effect on growth. Tetrahydropyrene 33, obtained by hydrolysis of the natural beta-glucosides 29 and 30 or by hemisynthesis from 1, is the most active compound, causing 90% inhibition of the growth at 2.5 x 10(-5) M concentration. Synthetic ai-glucosides 28, 31, and 32 showed comparable activity to those of 29 and 30.

  DOI：

  10.1007/bf02033657
• 作为产物：
  描述：

  6-methoxy-5-methyl-3,4-dihydro-2(1H)-naphthalenone 在 lithium aluminium tetrahydride 、 正丁基锂 、 potassium tert-butylate 、 水 、 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 79.67h， 生成 juncusol dimethyl ether
  参考文献：
  名称：

  Regiospecific total synthesis of juncusol

  摘要：

  DOI：

  10.1021/jo00195a034

文献信息

• Regiospecific total synthesis of juncusol
  作者：Dale L. Boger、Michael D. Mullican

  DOI：10.1021/jo00195a034

  日期：1984.10
• Action of antialgal compounds fromJuncus effusus L. onSelenastrum capricornutum
  作者：Marina Della Greca、Antonio Fiorentino、Pietro Monaco、Gabriele Pinto、Antonino Pollio、Lucio Previtera

  DOI：10.1007/bf02033657

  日期：1996.3

  Twenty-nine free and glucosylated dihydrophenanthrenes and tetrahydropyrenes isolated from Juncus effusus have been tested against the unicellular green alga Selenastrum capricornutum. The free compounds showed a strong inhibitory activity, while the glucosides were inactive or had a slight stimulating effect on growth. Tetrahydropyrene 33, obtained by hydrolysis of the natural beta-glucosides 29 and 30 or by hemisynthesis from 1, is the most active compound, causing 90% inhibition of the growth at 2.5 x 10(-5) M concentration. Synthetic ai-glucosides 28, 31, and 32 showed comparable activity to those of 29 and 30.