2-hydroxy-8-methylphenanthrene | 111589-12-9

• 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: 2-hydroxy-8-methylphenanthrene
• 英文别名: 8-methylphenanthren-2-ol；8-Methyl-[2]phenanthrol；1-Methyl-phenanthrol；7-Hydroxy-1-methyl-phenanthren；8-Methyl-2-phenanthrol
• CAS: 111589-12-9
• 化学式: C₁₅H₁₂O
• 分子量: 208.26
• InChiKey: TXSQEOUFZAGXJV-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C
• 沸点：
  416.4±14.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-hydroxy-8-methylphenanthrene 在 盐酸 、 potassium permanganate 、 三氯化铝 、 potassium carbonate 、 丙酮 、 苯 作用下， 生成 2-methoxy-8-methyl-phenanthrene-1-carboxylic acid
  参考文献：
  名称：

  Effect of Deinking Paper Sludge Compost On Nutrient Uptake and Yields of Snap Bean And Potatoes Grown in Rotation

  摘要：

  DOI：

  10.1080/1065657x.2001.10702025
• 作为产物：
  描述：

  N,N-二乙基-3-甲氧基苯甲酰胺 在 bis(acetylacetonate)nickel(II) 、 lithium chloro-isopropyl-magnesium chloride 、 四(三苯基膦)钯 、 四甲基乙二胺 、 四丁基氟化铵 、 仲丁基锂 、 三溴化硼 、 sodium hydride 、 sodium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 、 乙醇 、 二氯甲烷 、 环己烷 、 水 为溶剂， 反应 19.5h， 生成 2-hydroxy-8-methylphenanthrene
  参考文献：
  名称：

  Directed Metalation–Suzuki–Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes

  摘要：

  A general, efficient, and regioselective synthesis of a series of hydroxylated 1-methylphenanthrenes 9 by a combined directed ortho metalation (DoM)-Suzuki-Miyaura cross-coupling directed remote metalation (DreM) sequence is reported. Diversity to this methodology was achieved by a regioselective DoM rather than DreM reaction, affording more highly substituted phenanthrols (Table 2). Application of the turbo-Grignard reagent (i-PrMgCl-LiCl) in the Ni-catalyzed Corriu-Kumada reaction gave efficient decarbamoylation (Tables 3 and 4). Additional features are the TMS protecting group and halo-induced ipso-desilylation tactics applied to the regioselective synthesis of phenanthrenes (Scheme 2).

  DOI：

  10.1021/acs.joc.5b01300

文献信息

• ——
  作者：M. Dellagreca、A. Fiorentino、P. Monaco、A. Pollio、L. Previtera、A. Zarrelli

  DOI：10.1023/a:1005463802388

  日期：——

  9,10-Dihydrophenanthrenes and phenanthrenes, mimics of natural compounds with strong antialgal activity, have been synthesized through cross-coupling of 1-(2-iodo-5-methoxy)-phenylethanol with variously substituted iodobenzenes. The synthetic compounds, bearing a hydroxyl or a methoxyl group at C-2 and a methyl in the C ring, were tested against the green alga Selenastrum capricornutum. All compounds, except 2-methoxy-7-methylphenanthrene, caused inhibition of algal growth by more than 70% at 10(-4) M, and many of them retained this strong activity at 10(-5) M.
• Zur Kenntnis der Diterpene. (40. Mitteilung). Über die isomeren Tetraoxy-abietinsäuren und deren funktionelle Umwandlungsprodukte
  作者：L. Ruzicka、L. Sternbach

  DOI：10.1002/hlca.19400230142

  日期：——
• 70. Syntheses in the phenanthrene series. Part II. 7-Methoxy-1-methylphenanthrene and a new route to phenanthrene
  作者：W. F. Short、H. Stromberg、A. E. Wiles

  DOI：10.1039/jr9360000319

  日期：——
• 116. Totarol. Part I
  作者：W. F. Short、H. Stromberg

  DOI：10.1039/jr9370000516

  日期：——
• Brandt; Thomas, New Zealand Journal of Science and Technology, 1951, vol. <B> 33, p. 30,34
  作者：Brandt、Thomas

  DOI：——

  日期：——