(+/-)-10β-azido-7α,8β,9α-trihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: (+/-)-10β-azido-7α,8β,9α-trihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• 英文别名: (7S,8R,9R,10S)-10-azido-7,8,9,10-tetrahydrobenzo[a]pyrene-7,8,9-triol
• 化学式: C₂₀H₁₅N₃O₃
• 分子量: 345.357
• InChiKey: ZBINGRRBSKACLB-VNTMZGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-10β-azido-7α,8β,9α-trihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene 在 platinum(IV) oxide 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (+/-)-10β-amino-7α,8β,9α-tris(benzoyloxy)-7,8,9,10-tetrahydrobenzopyrene
  参考文献：
  名称：

  Improved High-Yield Synthesis of Polycyclic Aromatic Hydrocarbon Amino Tribenzoates, Nucleophilic Components for Synthesis of Diol Epoxide-Nucleoside Adducts

  摘要：

  This report describes an improved high-yield synthesis of amino tribenzoates derived through a trans-ring opening of diol expoxides. A significant difference in the relative reactivities of benzo[a]pyrene series-1 and series-2 diol epoxide diastereomers with LiN3 has been noted. Facile triacylation of the azido triols derived through this ring-opening with benzoyl cyanide and reduction using PtO2 afforded the corresponding amines in high yields.

  DOI：

  10.1080/00397919408010618
• 作为产物：
  描述：

  顺式-(-)-苯并(a)芘-7,8-二醇-9,10-环氧化物 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以79%的产率得到(+/-)-10β-azido-7α,8β,9α-trihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene
  参考文献：
  名称：

  Improved High-Yield Synthesis of Polycyclic Aromatic Hydrocarbon Amino Tribenzoates, Nucleophilic Components for Synthesis of Diol Epoxide-Nucleoside Adducts

  摘要：

  This report describes an improved high-yield synthesis of amino tribenzoates derived through a trans-ring opening of diol expoxides. A significant difference in the relative reactivities of benzo[a]pyrene series-1 and series-2 diol epoxide diastereomers with LiN3 has been noted. Facile triacylation of the azido triols derived through this ring-opening with benzoyl cyanide and reduction using PtO2 afforded the corresponding amines in high yields.

  DOI：

  10.1080/00397919408010618

文献信息

• A Novel Synthetic Method for Cis-Opened Benzo[<i>a</i>]pyrene 7,8-Diol 9,10-Epoxide Adducts at the Exocyclic <i>N</i>⁶-Amino Group of Deoxyadenosine
  作者：Anthony S. Pilcher、Haruhiko Yagi、Donald M. Jerina

  DOI：10.1021/ja980176p

  日期：1998.4.1
• Improved High-Yield Synthesis of Polycyclic Aromatic Hydrocarbon Amino Tribenzoates, Nucleophilic Components for Synthesis of Diol Epoxide-Nucleoside Adducts
  作者：Mahesh K. Lakshman、Surendrakumar Chaturvedi、Roland E. Lehr

  DOI：10.1080/00397919408010618

  日期：1994.11

  This report describes an improved high-yield synthesis of amino tribenzoates derived through a trans-ring opening of diol expoxides. A significant difference in the relative reactivities of benzo[a]pyrene series-1 and series-2 diol epoxide diastereomers with LiN3 has been noted. Facile triacylation of the azido triols derived through this ring-opening with benzoyl cyanide and reduction using PtO2 afforded the corresponding amines in high yields.