benzochrysene-11,12-dione | 122048-38-8

• 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: benzochrysene-11,12-dione
• 英文别名: benzo[g]chrysene-11,12-dione；Pentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2,4,6,8,10,12,15(20),16,21-decaene-18,19-dione
• CAS: 122048-38-8
• 化学式: C₂₂H₁₂O₂
• 分子量: 308.336
• InChiKey: KFMQTMDKTVDQEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzochrysene-11,12-dione 在 sodium tetrahydroborate 、 氧气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以83%的产率得到trans-11,12-dihydroxy-11,12-dihydrobenzochrysene
  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 、 potassium dihydrogenphosphate 、 palladium on activated charcoal 、 adogen 464 、 甲烷磺酸 、 potassium nitrososulfonate 、 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 21.5h， 生成 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

文献信息

• Detoxication of Structurally Diverse Polycyclic Aromatic Hydrocarbon (PAH) o-Quinones by Human Recombinant Catechol-O-methyltransferase (COMT) via O-Methylation of PAH Catechols
  作者：Li Zhang、Yi Jin、Mo Chen、Meng Huang、Ronald G. Harvey、Ian A. Blair、Trevor M. Penning

  DOI：10.1074/jbc.m111.240739

  日期：2011.7

  LC-MS/MS showed that each isomer was a mono-O-methylated metabolite. (1)H NMR was used to assign the predominant positional isomer of benzo[a]pyrene-7,8-catechol as the O-8-monomethylated catechol. The catalytic efficiency (k(cat)/K(m)) varied among different classes of PAH-catechols by 500-fold. The ability of S-COMT to produce two isomeric products from PAH-catechols was rationalized using the crystal

  多环芳烃 (PAH) 是环境和烟草致癌物。醛酮还原酶 (AKR) 对中间多环芳烃反式二氢二醇的代谢活化导致亲电子和氧化还原活性邻醌的形成。我们研究了人类重组可溶性儿茶酚-O-甲基转移酶 (S-COMT) 的 O-甲基化是否是氧化还原循环过程中产生的一组结构多样的多环芳烃-儿茶酚的可行解毒步骤。研究中使用了由 AKR 产生的 PAH 非 K 区邻醌类（湾区、甲基化湾区和峡湾区邻醌）类别。PAH 邻醌在厌氧条件下被二硫苏糖醇还原为相应的儿茶酚，然后在 S-[(3)H] 腺苷-l-甲硫氨酸作为甲基供体的情况下，由人类 S-COMT 进一步 O-甲基化。O-甲基化邻苯二酚的形成通过 HPLC-UV 结合在线辐射检测进行检测，未标记的产物也通过 LC-MS/MS 进行表征。人类 S-COMT 能够催化所有 PAH-儿茶酚的 O-甲基化，并产生两种不同比例的异构代谢物。LC-MS/MS 显示每个异构体都是单-O-甲基化代谢物。(1)
• Synthesis of optically active fjord-region 11,12-diol 13,14-epoxides and the K-region 9,10-oxide of the carcinogen benzo[g]chrysene
  作者：Daniel R. Bushman、Scott J. Grossman、Donald M. Jerina、Roland E. Lehr

  DOI：10.1021/jo00276a009

  日期：1989.7
• BUSHMAN, DANIEL R.;GROSSMAN, SCOTT J.;JERINA, DONALD M.;LEHR, ROLAND E., J. ORG. CHEM., 54,(1989) N5, C. 3533-3544
  作者：BUSHMAN, DANIEL R.、GROSSMAN, SCOTT J.、JERINA, DONALD M.、LEHR, ROLAND E.

  DOI：——

  日期：——
• 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.