cis-4,5-Dihydro-4,5-dihydroxy-3-nitropyrene | 91254-95-4

• 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: cis-4,5-Dihydro-4,5-dihydroxy-3-nitropyrene
• 英文别名: 4,5-Pyrenediol, 4,5-dihydro-3-nitro-, cis-；(4S,5R)-3-nitro-4,5-dihydropyrene-4,5-diol
• CAS: 91254-95-4
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: UERICTZYIDOLBM-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-4,5-Dihydro-4,5-dihydroxy-3-nitropyrene 在 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以80%的产率得到3-硝基-5H-菲并(4,5-bcd)吡喃-5-酮
  参考文献：
  名称：

  Superoxide oxidation of 1-nitropyrene-cis-dihydrodiols

  摘要：

  KO2 oxidation of cis-4,5-dihydro-4,5-dihydroxy-3-nitropyrene, 1 gives the known lactone, 3-nitro-5H-phenanthro[4,5-bcd]pyran-5-one, 2. Similarly the analogous 4,5-dihydrodiol, 3, gives the known lactone, 1-nitro-5H-phenanthro[4,5-bcd]pyran-5-one, 4. While the yield of 2 is 80%, it is only 16% for 4. A study of the latter oxidation, relying especially on the use of HPLC, led to a change in the conditions that increased the yield of 4 from 16 to 88%. The change was to quench the reaction with H2O2 shortly after it began instead of letting it proceed, as usual, for several hours before quenching with water.

  DOI：

  10.1016/s0040-4020(01)86519-4

文献信息

• Superoxide oxidation of 1-nitropyrene-cis-dihydrodiols
  作者：Samy Abdel-Baky、Chariklia Sotiriou-Leventis、Roger W. Giese

  DOI：10.1016/s0040-4020(01)86519-4

  日期：1991.7

  KO2 oxidation of cis-4,5-dihydro-4,5-dihydroxy-3-nitropyrene, 1 gives the known lactone, 3-nitro-5H-phenanthro[4,5-bcd]pyran-5-one, 2. Similarly the analogous 4,5-dihydrodiol, 3, gives the known lactone, 1-nitro-5H-phenanthro[4,5-bcd]pyran-5-one, 4. While the yield of 2 is 80%, it is only 16% for 4. A study of the latter oxidation, relying especially on the use of HPLC, led to a change in the conditions that increased the yield of 4 from 16 to 88%. The change was to quench the reaction with H2O2 shortly after it began instead of letting it proceed, as usual, for several hours before quenching with water.