9,10-Dihydro-[4]phenanthrol | 15067-24-0

• 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: 9,10-Dihydro-[4]phenanthrol
• 英文别名: 4-Hydroxy-9.10-dihydro-phenanthren；9,10-Dihydrophenanthren-4-ol
• CAS: 15067-24-0
• 化学式: C₁₄H₁₂O
• 分子量: 196.249
• InChiKey: YVHBATJHIHGOBA-UHFFFAOYSA-N

物化性质

• 沸点：
  380.6±21.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  9,10-Dihydro-[4]phenanthrol 、 硫酸二甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 生成 菲
  参考文献：
  名称：

  STUDIES IN THE PHENANTHRENE SERIES. XX. NITRATION OF 9,10-DIHYDROPHENANTHRENE^*

  摘要：

  DOI：

  10.1021/jo01221a006
• 作为产物：
  描述：

  4-nitro-9,10-dihydrophenanthrene 在 吡啶 、 乙醇 、 硫酸 、 铂 、 sodium nitrite 作用下， 生成 9,10-Dihydro-[4]phenanthrol
  参考文献：
  名称：

  STUDIES IN THE PHENANTHRENE SERIES. XX. NITRATION OF 9,10-DIHYDROPHENANTHRENE^*

  摘要：

  DOI：

  10.1021/jo01221a006

文献信息

• Mechanism of photoisomerization of xanthene to 6H-dibenzo[b,d]pyran in aqueous solution
  作者：C. G. Huang、Deepak Shukla、Peter Wan

  DOI：10.1021/jo00018a044

  日期：1991.8

  A new photoreaction, the photoisomerization of xanthene (1) to 6H-dibenzo[b,d]pyran (2) (almost-equal-to 70%) (PHI = 0.0035 in 7:3 H2O-CH3CN) in aqueous CH3CN solution is reported. In addition to 2, 2-benzylphenol (3) (PHI almost-equal-to 0.001), 9,9'-bixanthyl (4) (PHI < 0.001), and 2-(2'-hydroxyphenyl)benzyl alcohol (5) (PHI < 0.001) are also observed as minor products. 9-Methylxanthene (9) also photoisomerizes to the corresponding pyran derivative 10, although in this case much lower yields are observed due to secondary photochemistry of 10. The photoisomerization of 1 is most efficient in aqueous solution: PHI increased with increasing water content in a H2O-CH3CN solvent mixture. A mechanism of photoisomerization is proposed that involves initial Ar-O bond homolysis from S1, to generate a singlet biradical. Trivial recombination gives back unreacted 1. Hydrogen abstraction from solvent leads to the photoreduction product 3. However, recombination of the biradical at the ipso benzylic position (ortho to phenol) gives a cyclohexadienone intermediate 17. Subsequent transformation of this species to 2 occurs via an o-quinone methide intermediate 18, which itself can be trapped with MeOH or H2O, to give the corresponding methyl ether derivative 8 or alcohol 5.
• Photochemistry of phenoxybenzyl alcohols in aqueous solution: photosolvolysis vs. photorearrangement to 6H-dibenzo[b,d]pyrans
  作者：C. G. Huang、Peter Wan

  DOI：10.1021/jo00016a009

  日期：1991.8

  The photochemistry of three phenoxybenzyl alcohols (1-3) has been studied in MeOH, CH3CN, and in aqueous solution. It was found that both of the ortho-substituted phenoxybenzyl alcohols 1 and 2 gave the corresponding 6H-dibenzo[b,d]pyrans 6 and 10, via a mechanism believed to involve initial aryl C-O bond homolysis followed by rearrangement to give a 2-(2'-hydroxyphenyl)benzyl alcohol (biphenyl) derivative, which subsequently undergoes a photocyclization reaction to the corresponding 6H-dibenzo[b,d]pyran. The quantum yield for formation of 6 (from 1) was 0.0073 in neutral 6:4 H2O-CH3CN. Lower quantum yields for formation of 6 were observed on photolysis in pure organic solvents (PHI = 0.0015 in 100% CH3CN). The meta-substituted isomer 3 did not give any reaction via a similar photocyclization process: its photochemistry involves initial aryl C-O bond homolysis followed by simple radical recoupling to give isomeric hydroxybiphenyls, as well as products derived from radical escape. In aqueous sulfuric acid solution (pH < 2), a competing acid-catalyzed photosolvolysis reaction was observed for all of these compounds (i.e., C-OH bond heterolysis with assistance of hydronium ion); it was the only observed reaction in moderately concentrated sulfuric acid solution.
• Anion-Accelerated Palladium-Catalyzed Intramolecular Coupling of Phenols with Aryl Halides
  作者：D. David Hennings、Seiji Iwasa、Viresh H. Rawal

  DOI：10.1021/jo961876k

  日期：1997.1.1
• STUDIES IN THE PHENANTHRENE SERIES. XX. NITRATION OF 9,10-DIHYDROPHENANTHRENE^*
  作者：JOHN W. KRUEGER、ERICH MOSETTIG

  DOI：10.1021/jo01221a006

  日期：1938.9