(+/-)-7β,8α,9α-tris(benzoyloxy)-10β-azido-7,8,9,10-tetrahydrobenzopyrene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (+/-)-7β,8α,9α-tris(benzoyloxy)-10β-azido-7,8,9,10-tetrahydrobenzopyrene
• 英文别名: (+/-)-7β,8α,9α-tris(benzoyloxy)-10β-azido-7,8,9,10-tetrahydrobenzo[a]pyrene；[(7R,8S,9R,10S)-10-azido-7,8-dibenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyren-9-yl] benzoate
• 化学式: C₄₁H₂₇N₃O₆
• 分子量: 657.682
• InChiKey: RTSXCFFJSRKRLP-LQDUMDOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  8

上下游信息

反应信息

• 作为反应物：
  描述：

  (+/-)-7β,8α,9α-tris(benzoyloxy)-10β-azido-7,8,9,10-tetrahydrobenzopyrene 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.5h， 以92%的产率得到(+/-)-7β,8α,9α-tris(benzoyloxy)-10β-amino-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：

  (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 在 N₃^- form of Amberlite resin 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 35.17h， 生成 (+/-)-7β,8α,9α-tris(benzoyloxy)-10β-azido-7,8,9,10-tetrahydrobenzopyrene
  参考文献：
  名称：

  Regioselective ring opening of polycyclic aromatic hydrocarbon epoxides by polymer-supported azide anion

  摘要：

  DOI：

  10.1021/jo00303a025

文献信息

• Regioselective ring opening of polycyclic aromatic hydrocarbon epoxides by polymer-supported azide anion
  作者：Maheshkumar Lakshman、Durgesh V. Nadkarni、Roland E. Lehr

  DOI：10.1021/jo00303a025

  日期：1990.8
• 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.