2-[2-(9-菲基)乙基]环己酮 | 172288-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 2-[2-(9-菲基)乙基]环己酮
• 英文名称: 2-<2-(9-Phenanthryl)ethyl>cyclohexanone
• 英文别名: 2-(2-phenanthren-9-ylethyl)cyclohexan-1-one
• CAS: 172288-54-9
• 化学式: C₂₂H₂₂O
• 分子量: 302.416
• InChiKey: JAROEDJLZLIAEG-UHFFFAOYSA-N

物化性质

• 沸点：
  500.0±19.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-[2-(9-菲基)乙基]环己酮 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 苯并[G]屈 、 Benzo<4,5>cyclohept<1,2,3-jk>phenanthrene
  参考文献：
  名称：

  Efficient Syntheses of the anti- and syn-Diol Epoxide Metabolites of the Carcinogenic Polycyclic Aromatic Hydrocarbon Benzo[g]chrysene

  摘要：

  Two new synthetic approaches to the active fjord region anti- and syn-diol epoxide metabolites (3a and 3b) of the potent carcinogenic hydrocarbon benzo[g]chrysene are described. The first of these methods entails initial synthesis of the key intermediate 12-hydroxybenzo[g]chrysene which is transformed in two steps to trans-11,12-dihydroxy-11,12-dihydrobenzo[g]chrysene, the synthetic precursor of 3a and 3b. The second method involves in the key step oxidative photocyclization of a 1,2 diarylethylene having methoxy groups at appropriate sites for subsequent conversion to the dihydrodiol function. These methods allow efficient preparative scale synthesis of the benzo[g]chrysene diol epoxides required as starting compounds for the synthesis of specifically alkylated benzo[g]chrysene-oligonucleotide adducts needed for site-directed mutagenesis and other studies to elucidate molecular mechanisms of carcinogenesis.

  DOI：

  10.1021/jo00124a026
• 作为产物：
  描述：

  2-(9-Phenanthryl)ethanol mesylate 在 盐酸 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 39.0h， 生成 2-[2-(9-菲基)乙基]环己酮
  参考文献：
  名称：

  Efficient Syntheses of the anti- and syn-Diol Epoxide Metabolites of the Carcinogenic Polycyclic Aromatic Hydrocarbon Benzo[g]chrysene

  摘要：

  Two new synthetic approaches to the active fjord region anti- and syn-diol epoxide metabolites (3a and 3b) of the potent carcinogenic hydrocarbon benzo[g]chrysene are described. The first of these methods entails initial synthesis of the key intermediate 12-hydroxybenzo[g]chrysene which is transformed in two steps to trans-11,12-dihydroxy-11,12-dihydrobenzo[g]chrysene, the synthetic precursor of 3a and 3b. The second method involves in the key step oxidative photocyclization of a 1,2 diarylethylene having methoxy groups at appropriate sites for subsequent conversion to the dihydrodiol function. These methods allow efficient preparative scale synthesis of the benzo[g]chrysene diol epoxides required as starting compounds for the synthesis of specifically alkylated benzo[g]chrysene-oligonucleotide adducts needed for site-directed mutagenesis and other studies to elucidate molecular mechanisms of carcinogenesis.

  DOI：

  10.1021/jo00124a026