顺式-苯并(a)屈-11,12-二醇-13,14-环氧化物 | 119441-69-9

• 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: 顺式-苯并(a)屈-11,12-二醇-13,14-环氧化物
• 英文名称: trans-11,12-Dihydroxy-syn-13,14-epoxy-11,12,13,14-tetrahydrobenzochrysene
• 英文别名: Benzo(g)chrysene-11,12-dihydrodiol-13,14-epoxide；(16S,18R,19S,20R)-17-oxahexacyclo[12.9.0.02,7.08,13.015,21.016,18]tricosa-1(14),2,4,6,8,10,12,15(21),22-nonaene-19,20-diol
• CAS: 119441-69-9；132832-27-0；119479-44-6
• 化学式: C₂₂H₁₆O₃
• 分子量: 328.367
• InChiKey: GZHHSQMUVHHNOY-CLAROIROSA-N

物化性质

• 沸点：
  645.3±55.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  顺式-苯并(a)屈-11,12-二醇-13,14-环氧化物 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 以74%的产率得到14β-Amino-11β,12α,13α-trihydroxy-11,12,13,14-tetrahydrobenzochrysene
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00124a027
• 作为产物：
  描述：

  13β-bromo-11α,12β,14α-trihydroxy-11,12,13,14-tetrahydrobenzochrysene 在 Amberlyst IRA-400 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以97%的产率得到顺式-苯并(a)屈-11,12-二醇-13,14-环氧化物
  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

• 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：——