3,4,9,10-tetramethoxybenzo[s]picene | 201208-91-5

• 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: 3,4,9,10-tetramethoxybenzo[s]picene
• 英文别名: 6,7,22,23-Tetramethoxyhexacyclo[16.8.0.02,11.05,10.012,17.019,24]hexacosa-1(18),2(11),3,5(10),6,8,12,14,16,19(24),20,22,25-tridecaene
• CAS: 201208-91-5
• 化学式: C₃₀H₂₄O₄
• 分子量: 448.518
• InChiKey: WWDCWURWTFWVHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,9,10-tetramethoxybenzo[s]picene 在 sodium tetrahydroborate 、 三溴化硼 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 69.5h， 生成 (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：

  1,4-bis(2-vinyl-3,4-dimethoxyphenyl)naphthalene 在 1,2-环氧丁烷 、 碘 作用下， 以 苯 为溶剂， 反应 4.0h， 以81%的产率得到3,4,9,10-tetramethoxybenzo[s]picene
  参考文献：
  名称：

  多环芳烃及其致癌性氧化代谢产物的新合成方法：苯并[s] pic烯，苯并[rst]五苯酮和二苯并[b，def] derivatives的衍生物。

  摘要：

  描述了一种新的合成多环芳族化合物的方法，该方法需要在关键步骤中将PAH双硼酸衍生物与邻溴代芳基醛进行双Suzuki偶联，以提供芳基二醛，然后通过（a）转化为二烯烃将其转化为更大的多环芳环系统通过维蒂希反应，然后进行光环化，或（b）用三氟甲磺酸和1,3-丙二醇进行还原环化。这种合成方法可方便地从单个Suzuki偶联中间体访问多达三个不同的多环芳族环系统。它被用来合成苯并[s]吡啶，苯并[r]戊苯，二苯并[b，def]丙烯和13,14-二氢-苯并[g]茚并[2,1-a]芴的取代衍生物，以及苯并[s]]烯，苯并[rst]五苯芬的可能致癌的双二氢二醇代谢物，

  DOI：

  10.1021/jo9918044

文献信息

• New Synthetic Approaches to Polycyclic Aromatic Hydrocarbons and Their Carcinogenic Oxidized Metabolites:  Derivatives of Benzo[<i>s</i>]picene, Benzo[<i>r</i><i>st</i>]pentaphene, and Dibenzo[<i>b</i>,<i>d</i><i>ef</i>]chrysene
  作者：Fang-Jie Zhang、Cecilia Cortez、Ronald G. Harvey

  DOI：10.1021/jo9918044

  日期：2000.6.1

  synthetic method provides convenient access to as many as three different polycyclic aromatic ring systems from a single Suzuki coupled intermediate. It was utilized to synthesize substituted derivatives of benzo[s]picene, benzo[rst]pentaphene, dibenzo[b,def]chrysene, and 13,14-dihydro-benz[g]indeno[2,1-a]fluorene, as well as the putative carcinogenic bisdihydrodiol metabolites of benzo[s]picene, benzo[rst]pentaphene

  描述了一种新的合成多环芳族化合物的方法，该方法需要在关键步骤中将PAH双硼酸衍生物与邻溴代芳基醛进行双Suzuki偶联，以提供芳基二醛，然后通过（a）转化为二烯烃将其转化为更大的多环芳环系统通过维蒂希反应，然后进行光环化，或（b）用三氟甲磺酸和1,3-丙二醇进行还原环化。这种合成方法可方便地从单个Suzuki偶联中间体访问多达三个不同的多环芳族环系统。它被用来合成苯并[s]吡啶，苯并[r]戊苯，二苯并[b，def]丙烯和13,14-二氢-苯并[g]茚并[2,1-a]芴的取代衍生物，以及苯并[s]]烯，苯并[rst]五苯芬的可能致癌的双二氢二醇代谢物，
• 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.