1,2,9,10-tetraacetoxybenzo[c]chrysene | 216664-03-8

• 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: 1,2,9,10-tetraacetoxybenzo[c]chrysene
• 英文别名: (6,7,19-Triacetyloxy-18-pentacyclo[12.8.0.02,11.03,8.015,20]docosa-1(14),2(11),3(8),4,6,9,12,15(20),16,18,21-undecaenyl) acetate
• CAS: 216664-03-8
• 化学式: C₃₀H₂₂O₈
• 分子量: 510.5
• InChiKey: SKSCZLSSQBYABG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2,9,10-tetraacetoxybenzo[c]chrysene 在 sodium tetrahydroborate 、 氧气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以90%的产率得到trans-1,2-trans-9,10-tetrahydroxy-1,2,9,10-tetrahydrobenzo[c]chrysene
  参考文献：
  名称：

  Synthesis of Potentially Carcinogenic Higher Oxidized Metabolites of Dibenz[a,j]anthracene and Benzo[c]chrysene

  摘要：

  Bis(dihydrodiols) and other higher oxidized metabolites are implicated as active carcinogenic metabolites of polycyclic aromatic hydrocarbons, such as dibenz[a,j]anthracene, that possess more than one bay region in the molecule. The bis(dihydrodiol) metabolites may potentially undergo further metabolism to mono- or diepoxides that combine covalently with DNA, or undergo conversion to bis(catechols) that enter into a redox cycle with O-2 to form reactive oxygen species that attack DNA. This paper reports convenient syntheses of the terminal ring bis(dihydrodiol) derivatives of dibenz[a,j]anthracene (5) and benzo[c]chrysene (6) via routes that involve in the key steps double oxidative photocyclization of tetramethaxy-substituted diolefins. The latter are synthesized via double Wittig reaction of a bis(phosphonium) salt with 2,3-dimethoxybenzaldehyde. Demethylation of the bis(catechol) products followed by acetylation and reduction with NaBH4 in the presence of O-2 affords the bis(dihydrodiol) products. Several additional higher oxidized derivatives of dibenz[a,j]anthracene, specifically the 3,11-diphenol (14a), the 11-hydroxy-3,4-quinone (15), and the 11-hydroxy-trans-3,4- dihydro diol (2 c), are obtained by an alternative synthesis entailing the re action of the lithium salt of 1,4-dimethoxy-1,4-cyclohexadiene with 1,3-bis(iodoethyl)benzene to furnish a bis-alkylated diketone which undergoes acid-catalyzed cyclization to 3,1 l-diketododecahydrodibenz[a,j]anthracene.

  DOI：

  10.1021/jo980415r
• 作为产物：
  描述：

  1,2,9,10-tetramethoxybenzo[c]chrysene 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 1,2,9,10-tetraacetoxybenzo[c]chrysene
  参考文献：
  名称：

  Synthesis of Potentially Carcinogenic Higher Oxidized Metabolites of Dibenz[a,j]anthracene and Benzo[c]chrysene

  摘要：

  Bis(dihydrodiols) and other higher oxidized metabolites are implicated as active carcinogenic metabolites of polycyclic aromatic hydrocarbons, such as dibenz[a,j]anthracene, that possess more than one bay region in the molecule. The bis(dihydrodiol) metabolites may potentially undergo further metabolism to mono- or diepoxides that combine covalently with DNA, or undergo conversion to bis(catechols) that enter into a redox cycle with O-2 to form reactive oxygen species that attack DNA. This paper reports convenient syntheses of the terminal ring bis(dihydrodiol) derivatives of dibenz[a,j]anthracene (5) and benzo[c]chrysene (6) via routes that involve in the key steps double oxidative photocyclization of tetramethaxy-substituted diolefins. The latter are synthesized via double Wittig reaction of a bis(phosphonium) salt with 2,3-dimethoxybenzaldehyde. Demethylation of the bis(catechol) products followed by acetylation and reduction with NaBH4 in the presence of O-2 affords the bis(dihydrodiol) products. Several additional higher oxidized derivatives of dibenz[a,j]anthracene, specifically the 3,11-diphenol (14a), the 11-hydroxy-3,4-quinone (15), and the 11-hydroxy-trans-3,4- dihydro diol (2 c), are obtained by an alternative synthesis entailing the re action of the lithium salt of 1,4-dimethoxy-1,4-cyclohexadiene with 1,3-bis(iodoethyl)benzene to furnish a bis-alkylated diketone which undergoes acid-catalyzed cyclization to 3,1 l-diketododecahydrodibenz[a,j]anthracene.

  DOI：

  10.1021/jo980415r