10-hydroxy-10-(4-methylbenzyl)-phenanthren-9(10H)-one | 975-05-3

• 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: 10-hydroxy-10-(4-methylbenzyl)-phenanthren-9(10H)-one
• 英文别名: 9-Hydroxy-9-(4-methyl-benzyl)-10-oxo-9,10-dihydro-phenanthren；9,10-Dihydro-9-hydroxy-9-(p-methylbenzyl)-10-oxo-phenanthren；10-hydroxy-10-(4-methyl-benzyl)-10H-phenanthren-9-one；10-Hydroxy-10-(4-methyl-benzyl)-10H-phenanthren-9-on；10-Hydroxy-10-[(4-methylphenyl)methyl]phenanthren-9-one；10-hydroxy-10-[(4-methylphenyl)methyl]phenanthren-9-one
• CAS: 975-05-3
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: JBUKJZGPKMJXMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-hydroxy-10-(4-methylbenzyl)-phenanthren-9(10H)-one 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 氢气 、 乙酸酐 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 6-(p-Tolyl)-dibenzocycloheptan
  参考文献：
  名称：

  Transformation Products of the Photoadduct of p-Xylene and Phenanthrenequinone. Some Two- and Three-Atom Bridged Biphenyls¹

  摘要：

  DOI：

  10.1021/jo01034a050
• 作为产物：
  描述：

  9-(4-methylbenzyl)phenanthrene 在 吡啶 、 chromium(VI) oxide 、 四氧化锇 作用下， 生成 10-hydroxy-10-(4-methylbenzyl)-phenanthren-9(10H)-one
  参考文献：
  名称：

  Transformation Products of the Photoadduct of p-Xylene and Phenanthrenequinone. Some Two- and Three-Atom Bridged Biphenyls¹

  摘要：

  DOI：

  10.1021/jo01034a050

文献信息

• Photochemical Reaction of 9,10-Phenanthrenequinone with Hydrogen Donors. Behavior of Radicals in Solution as Studied by CIDNP
  作者：Kazuhiro Maruyama、Tetsuo Otsuki、Yoshinori Naruta

  DOI：10.1246/bcsj.49.791

  日期：1976.3

  Behavior of radicals produced in the photochemical reaction of 9,10-phenanthrenequinone was investigated by use of CIDNP and ESR technique. By comparison of the sign of CIDNP signals in formation of and in decomposition (photochemical or thermal) of adducts, the rearrangement of adducts, e.g., from the 1,2-adduct to 1,4-adduct and vice versa, was proposed. Although the adducts are stable enough to

  利用CIDNP和ESR技术研究了9,10-菲醌光化学反应中产生的自由基行为。通过比较加合物形成和分解（光化学或热）中 CIDNP 信号的符号，提出了加合物的重排，例如从 1,2-加合物到 1,4-加合物，反之亦然。虽然加合物足够稳定，通常可以分离，但它们通过光化学或热分解得到 9,10-菲二醇（或其醌氢醌）、氢供体的脱氢二聚体和其他次要产物的混合物。
• Products of photoreduction of 9,10-phenanthrenequinone in the presence of N,N-dimethylanilines and polymethylbenzenes
  作者：M.P. Shurygina、Yu.A. Kurskii、S.A. Chesnokov、G.A. Abakumov

  DOI：10.1016/j.tet.2007.11.050

  日期：2008.2

  Photoreduction of 9,10-phenanthrenequinone (PQ) in the presence of p-substituted N,N-dimethylanilines and polymethylbenzenes affords corresponding phenolethers as primary products. In the subsequent process shielded from light, phenolethers, which were formed by photoreaction of PQ with N,N-dimethylanilines, were quantitatively converted to give corresponding ketols. Phenolethers of 9,10-phenanthrenequinone

  在对位取代的N，N-二甲基苯胺和聚甲基苯存在下，对9,10-菲醌（PQ）进行光还原，可得到相应的酚醚作为主要产物。在随后的避光方法中，将PQ与N，N-二甲基苯胺的光反应形成的酚醚定量转化为相应的酮醇。9，10-菲醌和聚甲基苯的酚醚仅在辐射下和在存在第二个PQ分子的情况下才重新排列，形成酮醇。酚醚的稳定性取决于氧化还原性质和氢供体的结构。
• Polar effects in free radical reactions. The mechanism of photochemical addition of ethers and substituted toluenes to 9,10-phenanthrenequinone
  作者：Mordecai B. Rubin、Pauline Zwitkowits

  DOI：10.1016/s0040-4039(01)84006-5

  日期：1965.1
• Rubin; Zwitkowits, Journal of Organic Chemistry, 1964, vol. 29, p. 2362,2366
  作者：Rubin、Zwitkowits

  DOI：——

  日期：——
• Transformation Products of the Photoadduct of p-Xylene and Phenanthrenequinone. Some Two- and Three-Atom Bridged Biphenyls¹
  作者：Mordecai B. Rubin

  DOI：10.1021/jo01034a050

  日期：1964.11