3,4,10,11-tetrahydroxydibenz[a,j]anthracene | 216664-08-3

• 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: 3,4,10,11-tetrahydroxydibenz[a,j]anthracene
• 英文别名: Pentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),2,4(9),5,7,10,12,15,17(22),18,20-undecaene-7,8,18,19-tetrol
• CAS: 216664-08-3
• 化学式: C₂₂H₁₄O₄
• 分子量: 342.351
• InChiKey: RJFZDLBOFHGRBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 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：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,10,11-tetrahydroxydibenz[a,j]anthracene 在 吡啶 、 sodium tetrahydroborate 、 氧气 作用下， 以 乙醇 为溶剂， 反应 152.0h， 生成 trans-3,4-trans-10,11-tetrahydroxy-3,4,10,11-tetrahydrodibenz[a,j]anthracene tetraacetate
  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：

  3,4,10,11-tetramethoxydibenz[a,j]anthracene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到3,4,10,11-tetrahydroxydibenz[a,j]anthracene
  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

文献信息

• Synthesis of Potentially Carcinogenic Higher Oxidized Metabolites of Dibenz[<i>a,j</i>]anthracene and Benzo[<i>c</i>]chrysene
  作者：Ronald G. Harvey、Wei Dai、Jin-Tao Zhang、Cecilia Cortez

  DOI：10.1021/jo980415r

  日期：1998.11.1

  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.