trans-11,12-dihydroxy-11,12-dihydrobenzochrysene | 122048-37-7

• 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: trans-11,12-dihydroxy-11,12-dihydrobenzochrysene
• 英文别名: trans-11,12-dihydroxy-11,12-dihydrobenzo[g]chrysene；(18S,19S)-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-diol
• CAS: 122048-37-7；122090-55-5；122090-56-6；132832-24-7
• 化学式: C₂₂H₁₆O₂
• 分子量: 312.368
• InChiKey: SDYNFQRWECLVDP-UNMCSNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-11,12-dihydroxy-11,12-dihydrobenzochrysene 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以95%的产率得到(+)-anti-benzo[g]chrysene 11,12-dihydrodiol 13,14-epoxide
  参考文献：
  名称：

  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

  摘要：

  DOI：

  10.1021/jo00276a009
• 作为产物：
  描述：

  13,14-dihydrobenzochrysene 在 吡啶 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 敌草腈 、 氨 、 碳酸氢钠 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 73.83h， 生成 trans-11,12-dihydroxy-11,12-dihydrobenzochrysene
  参考文献：
  名称：

  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

  摘要：

  DOI：

  10.1021/jo00276a009

文献信息

• Synthesis of the Fjord-region cis- and trans-Amino Triol Derivatives of the Carcinogenic Hydrocarbon Benzo[g]chrysene and Utilization for the Synthesis of a Deoxyadenosine Adduct Linked to the N6-Amino Group
  作者：Alexander S. Kiselyov、Thomas Steinbrecher、Ronald G. Harvey

  DOI：10.1021/jo00124a027

  日期：1995.9

  Efficient syntheses of the complete set of four diastereomeric fjord-region amino triol derivatives of benzo[g]chrysene in which the amino group in the 14-position and the adjacent 13-hydroxyl group are trans or cis to one another (trans- and cis-5 and 6) is described. This is the first description of the syntheses of the bay- or fjord-region cis-amino triol derivatives of any carcinogenic polycyclic aromatic hydrocarbon(PAH). The amino triols are key synthetic precursors of PAH-oligonucleotide adducts in which the PAH moiety is covalently linked to the exocyclic amino groups of deoxyadenosine or deoxyguanosine. Formation of adducts of this type via reaction of a PAH diol epoxide metabolite with DNA is believed to be a critical step in the mechanism of PAH carcinogenesis. The synthetic amino triol isomers may be used to synthesize PAH-oligonucleotides needed for site-directed mutagenesis studies to relate isomer structural differences to their effects on DNA replication.
• 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.
• 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：——