4-hydroxybenzo[ghi]fluoranthene | 255871-53-5

• 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: 4-hydroxybenzo[ghi]fluoranthene
• 英文别名: Pentacyclo[8.8.0.02,7.03,17.013,18]octadeca-1(10),2,4,6,8,11,13(18),14,16-nonaen-5-ol
• CAS: 255871-53-5
• 化学式: C₁₈H₁₀O
• 分子量: 242.277
• InChiKey: SCJAQVFYSVALQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-hydroxybenzo[ghi]fluoranthene 在 potassium dihydrogenphosphate 、 adogen 464 、 potassium nitrososulfonate 作用下， 以 水 、 苯 为溶剂， 反应 0.5h， 生成 Benzo[ghi]fluoranthene-4,5-dione 、 benzo[ghi]fluoranthene-3,4-dione
  参考文献：
  名称：

  Synthesis of anti- and syn-Diol Epoxides of trans-3,4-Dihydroxy-3,4-dihydrobenzo[ghi]fluoranthene: Model Planar Diol Epoxides

  摘要：

  We describe the preparation of anti- and syn-3,4-dihydroxy-5,5a-epoxy-3,4,5,5a-tetrahydrobenzo[ghi]fluoranthene (2 and 3) as model planar diol epoxides. These compounds were synthesized by a dihydroarene method in 10 steps starting from 4H-cyclopenta[def]phenanthrene. These are the first examples of diol epoxides in which a five-membered ring is fused to the saturated ring bearing an epoxide group, and they are the rigid analogues of the extensively studied benzo[c]phenanthrene diol epoxides (5 and 6). In accord with expectation, (1)H NMR data indicated that the diol conformations of 2 and 3 are locked into diequatorial and diaxial conformations, respectively, and thus are suitable for comparative DNA binding studies.

  DOI：

  10.1021/jo9907944
• 作为产物：
  描述：

  4-(2'-carboxyethyl)-4H-cyclopenta[def]phenanthrene 在 sodium tetrahydroborate 、 氢氟酸 、 碘 、 sodium methylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 苯 为溶剂， 反应 9.17h， 生成 4-hydroxybenzo[ghi]fluoranthene
  参考文献：
  名称：

  Synthesis of anti- and syn-Diol Epoxides of trans-3,4-Dihydroxy-3,4-dihydrobenzo[ghi]fluoranthene: Model Planar Diol Epoxides

  摘要：

  We describe the preparation of anti- and syn-3,4-dihydroxy-5,5a-epoxy-3,4,5,5a-tetrahydrobenzo[ghi]fluoranthene (2 and 3) as model planar diol epoxides. These compounds were synthesized by a dihydroarene method in 10 steps starting from 4H-cyclopenta[def]phenanthrene. These are the first examples of diol epoxides in which a five-membered ring is fused to the saturated ring bearing an epoxide group, and they are the rigid analogues of the extensively studied benzo[c]phenanthrene diol epoxides (5 and 6). In accord with expectation, (1)H NMR data indicated that the diol conformations of 2 and 3 are locked into diequatorial and diaxial conformations, respectively, and thus are suitable for comparative DNA binding studies.

  DOI：

  10.1021/jo9907944