5-acetyl-2,6-dihydroxy-1,7-dimethyl-9,10-dihydrophenanthrene | 77305-81-8

• 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: 5-acetyl-2,6-dihydroxy-1,7-dimethyl-9,10-dihydrophenanthrene
• 英文别名: juncunone；1-(3,7-Dihydroxy-2,8-dimethyl-9,10-dihydro-4-phenanthrenyl)ethanone；1-(3,7-dihydroxy-2,8-dimethyl-9,10-dihydrophenanthren-4-yl)ethanone
• CAS: 77305-81-8
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: KDADJLHRXRSXQU-UHFFFAOYSA-N

物化性质

• 沸点：
  498.1±45.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-acetyl-2,6-dihydroxy-1,7-dimethyl-9,10-dihydrophenanthrene 在 lithium aluminium tetrahydride 作用下， 生成 5-(1-Hydroxy-ethyl)-1,7-dimethyl-9,10-dihydro-phenanthrene-2,6-diol
  参考文献：
  名称：

  Cytotoxic 9,10-Dihydrophenanthrenes from Juncus effusus L.

  摘要：

  Nine 9,10-dihydrophenanthrenes, seven of them described for the first time, have been isolated in a further investigation of Juncus effusus. The structures have been defined on the basis of the spectral properties of the compounds. All the dehydrophenanthrene metabolites present in the plant have been tested for their cytotoxic properties and many of them have been found to have a good in vitro activity.

  DOI：

  10.1016/s0040-4020(01)90169-3
• 作为产物：
  描述：

  2-氯-4-甲氧基-5-甲基苄基氯 在 palladium on activated charcoal manganese(IV) oxide 、 sodium hydroxide 、 正丁基锂 、 lithium methanolate 、 氢气 、 溴 、 三氯化硼 、 三溴化硼 、 potassium carbonate 、 magnesium 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 281.5h， 生成 5-acetyl-2,6-dihydroxy-1,7-dimethyl-9,10-dihydrophenanthrene
  参考文献：
  名称：

  junonenone的合成：一种来自君子兰的不寻常的二氢菲

  摘要：

  据报道，有效合成了遗传学上不常见的9,10-二氢菲，jununone。关键步骤涉及通过活化镁诱导的分子内均溶取代将（Z）-2-氯苯乙烯与菲进行闭环。

  DOI：

  10.1039/c39820001198

文献信息

• Carvalho, Christopher F.; Sargent, Melvyn V., Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1913 - 1918
  作者：Carvalho, Christopher F.、Sargent, Melvyn V.

  DOI：——

  日期：——
• Structure of juncunone: a biogenetically intriguing molecule from the marsh plant Juncus roemerianus
  作者：D. Howard Miles、Shirley Randle、Riz Shakir、Jerry L. Atwood

  DOI：10.1021/jo00326a049

  日期：1981.6
• Synthesis of juncunone: an unusual dihydrophenanthrene from Juncus roemerianus
  作者：Christopher F. Carvalho、Melvyn V. Sargent

  DOI：10.1039/c39820001198

  日期：——

  A efficient synthesis of the biogenetically unusual 9,10-dihydrophenanthrene, juncunone, is reported; the key step involves ring-closure of a (Z)-2-chlorostilbene to a phenanthrene by an intramolecular homolytic substitution induced by activated magnesium.

  据报道，有效合成了遗传学上不常见的9,10-二氢菲，jununone。关键步骤涉及通过活化镁诱导的分子内均溶取代将（Z）-2-氯苯乙烯与菲进行闭环。
• Cytotoxic 9,10-Dihydrophenanthrenes from Juncus effusus L.
  作者：Marina Della Greca、Antonio Fiorentino、Lorenzo Mangoni、Antonio Molinaro、Pietro Monaco、Lucio Previtera

  DOI：10.1016/s0040-4020(01)90169-3

  日期：1993.4

  Nine 9,10-dihydrophenanthrenes, seven of them described for the first time, have been isolated in a further investigation of Juncus effusus. The structures have been defined on the basis of the spectral properties of the compounds. All the dehydrophenanthrene metabolites present in the plant have been tested for their cytotoxic properties and many of them have been found to have a good in vitro activity.