trans-3,4-trans-9,10-tetrahydroxy-3,4,9,10-tetrahydrobenzo[c]picene | 201208-94-8

• 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: trans-3,4-trans-9,10-tetrahydroxy-3,4,9,10-tetrahydrobenzo[c]picene
• 英文别名: (6S,7S,22R,23R)-hexacyclo[16.8.0.02,11.05,10.012,17.019,24]hexacosa-1(18),2(11),3,5(10),8,12,14,16,19(24),20,25-undecaene-6,7,22,23-tetrol
• CAS: 201208-94-8
• 化学式: C₂₆H₂₀O₄
• 分子量: 396.442
• InChiKey: NBVJEMJHDNHSBR-MNHALERFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  trans-3,4-trans-9,10-tetrahydroxy-3,4,9,10-tetrahydrobenzo[c]picene 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到(6R,7S,8S,10R,21S,23R,24R,25S)-9,22-dioxaoctacyclo[17.9.0.02,12.05,11.08,10.013,18.020,26.021,23]octacosa-1(19),2(12),3,5(11),13,15,17,20(26),27-nonaene-6,7,24,25-tetrol
  参考文献：
  名称：

  Syntheses of Fjord Region Bis-dihydrodiol and Bis-anti-diol Epoxide Metabolites of Benzo[s]picene

  摘要：

  Efficient syntheses of the trans-3,4-trans-9,10-tetrahydroxy-3,4,9,10-tetrahydro derivatives of benzo[s]picene and the corresponding bis-anti-diol epoxide derivatives in which the epoxide rings lie in the sterically crowded fjord regions are reported. Bis-dihydrodiols and bis-anti-diol epoxides of this type are suspected as proximate and ultimate carcinogenic metabolites, respectively, of several polycyclic aromatic hydrocarbons. These are the first examples of this class of molecules to be synthesized, The syntheses entail in the key step double oxidative photocyclization of a tetramethoxy-2,3-distyrylnaphthalene obtained from double Wittig reaction of naphthalene-2,3-dialdehyde. The bis-dihydrodiols were obtained as a mixture of meso and racemic diastereomers separable by HPLC on a reversed-phase ZORBAX ODS column. The bis-anti-diol epoxide enantiomers derived from the latter were resolved by HPLC on a chiral column.

  DOI：

  10.1021/jo971666n
• 作为产物：
  描述：

  3,4,9,10-tetramethoxybenzo[s]picene 在 sodium tetrahydroborate 、 三溴化硼 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 67.5h， 生成 trans-3,4-trans-9,10-tetrahydroxy-3,4,9,10-tetrahydrobenzo[c]picene
  参考文献：
  名称：

  Syntheses of Fjord Region Bis-dihydrodiol and Bis-anti-diol Epoxide Metabolites of Benzo[s]picene

  摘要：

  Efficient syntheses of the trans-3,4-trans-9,10-tetrahydroxy-3,4,9,10-tetrahydro derivatives of benzo[s]picene and the corresponding bis-anti-diol epoxide derivatives in which the epoxide rings lie in the sterically crowded fjord regions are reported. Bis-dihydrodiols and bis-anti-diol epoxides of this type are suspected as proximate and ultimate carcinogenic metabolites, respectively, of several polycyclic aromatic hydrocarbons. These are the first examples of this class of molecules to be synthesized, The syntheses entail in the key step double oxidative photocyclization of a tetramethoxy-2,3-distyrylnaphthalene obtained from double Wittig reaction of naphthalene-2,3-dialdehyde. The bis-dihydrodiols were obtained as a mixture of meso and racemic diastereomers separable by HPLC on a reversed-phase ZORBAX ODS column. The bis-anti-diol epoxide enantiomers derived from the latter were resolved by HPLC on a chiral column.

  DOI：

  10.1021/jo971666n

文献信息

• Syntheses of Fjord Region Bis-dihydrodiol and Bis-<i>anti</i>-diol Epoxide Metabolites of Benzo[<i>s</i>]picene
  作者：Fang-Jie Zhang、Ronald G. Harvey

  DOI：10.1021/jo971666n

  日期：1998.2.1

  Efficient syntheses of the trans-3,4-trans-9,10-tetrahydroxy-3,4,9,10-tetrahydro derivatives of benzo[s]picene and the corresponding bis-anti-diol epoxide derivatives in which the epoxide rings lie in the sterically crowded fjord regions are reported. Bis-dihydrodiols and bis-anti-diol epoxides of this type are suspected as proximate and ultimate carcinogenic metabolites, respectively, of several polycyclic aromatic hydrocarbons. These are the first examples of this class of molecules to be synthesized, The syntheses entail in the key step double oxidative photocyclization of a tetramethoxy-2,3-distyrylnaphthalene obtained from double Wittig reaction of naphthalene-2,3-dialdehyde. The bis-dihydrodiols were obtained as a mixture of meso and racemic diastereomers separable by HPLC on a reversed-phase ZORBAX ODS column. The bis-anti-diol epoxide enantiomers derived from the latter were resolved by HPLC on a chiral column.