dibenzo[c,g]phenanthren-10-ol | 115123-31-4

• 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: dibenzo[c,g]phenanthren-10-ol
• 英文别名: Pentacyclo[12.8.0.02,11.03,8.017,22]docosa-1(14),2(11),3(8),4,6,9,12,15,17,19,21-undecaen-4-ol
• CAS: 115123-31-4；1428583-65-6；1428583-66-7
• 化学式: C₂₂H₁₄O
• 分子量: 294.353
• InChiKey: XCUWOVRZAGZONJ-UHFFFAOYSA-N

物化性质

• 沸点：
  581.7±19.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 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：

  右旋樟脑-10-磺酰氯 、 dibenzo[c,g]phenanthren-10-ol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到(M)-(-)-dibenzo[c,g]phenanthren-10-yl ((1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate
  参考文献：
  名称：

  Synthesis and Resolution of Substituted [5]Carbohelicenes

  摘要：

  Three types of racemic [5]helicenyl acetates (la, 2, and 3a) were synthesized. The synthesis of 2 was achieved by regioselective oxidation using o-iodoxybenzoic acid. The enzymatic kinetic resolution of la-3a was studied. The conversion with the highest rate and ee was obtained using la as the substrate and lipase Amano PS-IM as the enzyme. The two enantiomers of 1-[5]helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.

  DOI：

  10.1021/acs.joc.5b00759
• 作为产物：
  描述：

  3-乙炔基-4-(2-甲氧基苯基)菲 在 gold(III) chloride 、 sodium hydride 、 乙硫醇 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 dibenzo[c,g]phenanthren-10-ol
  参考文献：
  名称：

  Synthesis of [5]Helicenes with a Substituent Exclusively on the Interior Side of the Helix by Metal-catalyzed Cycloisomerization

  摘要：

  [5]Helicenes with a substituent exclusively oriented toward the interior curvature of the helix are synthesized by metal-catalyzed cycloisomerization. In addition, novel azulene-fused helicenes have been found through cycloisomerization studies. These [5]helicenes shows a high enough configurationally stability to allow resolution by HPLC on a chiral stationary phase.

  DOI：

  10.1021/ol400332j