12-Hydroxybenzochrysene | 115187-67-2

• 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: 12-Hydroxybenzochrysene
• 英文别名: 12-hydroxybenzo[g]chrysene；Pentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2,4,6,8,10,12,15(20),16,18,21-undecaen-18-ol
• CAS: 115187-67-2
• 化学式: C₂₂H₁₄O
• 分子量: 294.353
• InChiKey: YVQMLYRCEDKFLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220 °C
• 沸点：
  581.7±19.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  12-Hydroxybenzochrysene 在 potassium dihydrogenphosphate 、 adogen 464 、 potassium nitrososulfonate 作用下， 反应 1.0h， 以88%的产率得到benzochrysene-11,12-dione
  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-菲基)乙醇 在 六甲基磷酰三胺 、 palladium on activated charcoal 、 甲烷磺酸 、 叔丁基锂 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 20.5h， 生成 12-Hydroxybenzochrysene
  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

文献信息

• Substituent Effects and Charge Delocalization Mode in Chrysenium, Benzo[<i>c</i>]phenanthrenium, and Benzo[<i>g</i>]chrysenium Cations:  A Stable Ion and Electrophilic Substitution Study
  作者：Kenneth K. Laali、Takao Okazaki、Subodh Kumar、Sergio E. Galembeck

  DOI：10.1021/jo001268b

  日期：2001.2.1

  disubstituted chrysenes Ch (5- methyl- 3, 2-methoxy- 19, 2-methoxy-11-methyl- 20, 2-methoxy-5-methyl- 21, and 9-methyl-4H-cyclopenta[def]chrysene 22), monosubstituted benzo[c]phenanthrenes BcPh (3-methoxy- 23, 3-hydroxy- 24), and monosubstituted benzo[g]chrysenes BgCh (12-methoxy- 25; 12-hydroxy- 26) were generated in FSO3H/SO2ClF or FSO3H-SbF5 (4:1)/SO2ClF and studied by low-temperature NMR at 500 MHz. The methoxy

  衍生自单取代和双取代的Ch（5-甲基-3、2-甲氧基-19、2-甲氧基-11-甲基-20、2-甲氧基-5-甲基-21和9-甲基-4H-环戊[def] ch 22），单取代的苯并[c]菲BcPh（3-甲氧基-23、3-羟基-24）和单取代的苯并[g] ch BgCh（12-甲氧基25; 12-羟基26）在FSO3H / SO2ClF或FSO3H-SbF5（4：1）/ SO2ClF中生成，并通过500 MHz的低温NMR研究。甲氧基和甲基取代基将质子化指向它们各自的邻位。母体Ch 1在C-6 / C-12质子化，而3在C-6（3aH +）和C-12（3bH +）质子化，后者是热力学阳离子。2-甲氧基-Ch 19在C-1处质子化，得到两个构象上不同的碳鎓离子（19aH + / 19bH +）。在二取代的Ch衍生物20和21中，2-甲氧基取代了5-甲基，并且形成的主要碳阳离子通过对甲氧基的邻位攻击
• A New and Concise Synthesis of 3-Hydroxybenzo[<i>c</i>]phenanthrene and 12-Hydroxybenzo[<i>g</i>]chrysene, Useful Intermediates for the Synthesis of Fjord-Region Diol Epoxides of Benzo[<i>c</i>]phenanthrene and Benzo[<i>g</i>]chrysene
  作者：Subodh Kumar

  DOI：10.1021/jo9712355

  日期：1997.11.1

  the hydroxy analogues 5 and 6, respectively. The availability of this short and high-yielding regiospecific method for the synthesis of phenols 5 and 6 should allow the preparative-scale synthesis of the fjord-region diol epoxides 3 and 4. These diol epoxides are required as starting compounds for the synthesis of site-specifically modified oligonucleotides which are critically needed to elucidate the

  为了快速合成3-羟基苯并[c]菲（5）和12-羟基苯并[g] ch（6），已经开发了一种涉及钯催化的交叉偶联反应的新策略。这些酚类化合物是合成苯并[c]菲（1）和苯并[g] ch（2）的高度致癌的峡湾区二醇环氧代谢物3和4的关键中间体。2-溴-5-甲氧基苯甲醛（9）与萘-1-硼酸（7）和菲-9硼酸（8）的交叉偶联反应生成2-（1-萘基）-5-甲氧基苯甲醛（10 ）和2-（9-菲基）-5-甲氧基苯甲醛（11）的定量收率。这些醛与三甲基碘化碘在相转移条件下反应，或与由（甲氧基甲基）三苯基溴化and和苯基锂制得的Wittig试剂反应生成环氧乙烷基或甲氧基乙烯侧链，然后用甲磺酸（或三氟化硼）进行酸催化的环化反应3-甲氧基苯并[c]菲（16）和12-甲氧基苯并[g] ch（17）的产率为61-64％。最后，用三溴化硼将这些甲氧基衍生物16和17脱甲基，分别形成羟基类似物5和6。这种用于合成酚5和6的
• MONOBENZOCHRYSENE DERIVATIVES AND THEIR USE IN MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES
  申请人：Idemitsu Kosan Co., Ltd.

  公开号：EP2213639B1

  公开（公告）日：2016-04-13
• Efficient Syntheses of the anti- and syn-Diol Epoxide Metabolites of the Carcinogenic Polycyclic Aromatic Hydrocarbon Benzo[g]chrysene
  作者：Alexander S. Kiselyov、Hongmee Lee、Ronald G. Harvey

  DOI：10.1021/jo00124a026

  日期：1995.9

  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.