2,3:6,7-dibenzobicyclo<3.2.1>nona-2,6-diene | 38899-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2,3:6,7-dibenzobicyclo<3.2.1>nona-2,6-diene
• 英文别名: 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene；2,3:6,7-Dibenzo-bicyclo<3.3.1>nonadien-(2,6)；2,3:6,7-Dibenzobicyclo<3.3.1>nona-2,6-dien；2,3:6,7-Dibenzobicyclo[3.3.1]nona-2,6-dien；Tetracyclo[7.7.1.02,7.010,15]heptadeca-2,4,6,10,12,14-hexaene
• CAS: 38899-48-8
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: QDBTYACURFVKTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-benzyl-3,4-dihydro-1H-naphthalen-2-one 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 、 二硫化碳 为溶剂， 反应 32.0h， 生成 2,3:6,7-dibenzobicyclo<3.2.1>nona-2,6-diene
  参考文献：
  名称：

  Cyclialkylation studies. 3. Acid-catalyzed cyclodehydration of some benzyltetralols, with and without rearrangement, to yield tetracyclic hydrocarbons

  摘要：

  Acid-catalyzed cyclodehydration of some benzyltetralols has been used to prepare tetracyclic hydrocarbons as synthons for compounds of potential pharmacological value. Upon treatment with sulfuric acid at 25 or 40-degrees-C, 4-benzyl-2-tetralol (15) gave a 70:30 mixture of 2,3:6,7-dibenzobicyclo[3.2.2]nona-2,6-diene (7) and 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene (8). Reaction of 15 with p-toluenesulfonic acid in refluxing cyclohexane solution gave the same two products (7 and 8) as well as a small amount of 1-benzyl-1,2-dihydronaphthalene (16). Treatment of either 15 or 16 with AlCl3 gave only 8. Treatment of 1-benzyl-2-tetralol (17) with AlCl3 also gave 8. The mechanism of formation of 7 and 8 from 15 and 16 is discussed.

  DOI：

  10.1021/jo00009a013

文献信息

• Stetter,H.; Reischl,A., Chemische Berichte, 1960, vol. 93, p. 791 - 795
  作者：Stetter,H.、Reischl,A.

  DOI：——

  日期：——
• New Friedel-Crafts chemistry. XXV. Friedel-Crafts cyclialkylations and bicyclialkylations with diphenylalkyl chlorides
  作者：Royston Murphy Roberts、Gilbert Philip Anderson、Ali A. Khalaf、Chow-Eng Low

  DOI：10.1021/jo00821a016

  日期：1971.11
• A new conglomerate in a series of 2,3:6,7-dibenzobicyclo[3.3.1]nonanes
  作者：Pavel A. Levkin、Konstantin A. Lyssenko、Volker Schurig、Remir G. Kostyanovsky

  DOI：10.1070/mc2003v013n03abeh001747

  日期：2003.1

  Using enantioselective gas chromatography and X-ray diffraction analysis, we found that compound 2 forms a conglomerate (space group P2(1)2(1)2), whereas, according to X-ray diffraction data, compound 3 crystallises as a racemic compound (space group Pccn).
• Cyclialkylation studies. 3. Acid-catalyzed cyclodehydration of some benzyltetralols, with and without rearrangement, to yield tetracyclic hydrocarbons
  作者：Ramanujam S. Prasad、Royston M. Roberts

  DOI：10.1021/jo00009a013

  日期：1991.4

  Acid-catalyzed cyclodehydration of some benzyltetralols has been used to prepare tetracyclic hydrocarbons as synthons for compounds of potential pharmacological value. Upon treatment with sulfuric acid at 25 or 40-degrees-C, 4-benzyl-2-tetralol (15) gave a 70:30 mixture of 2,3:6,7-dibenzobicyclo[3.2.2]nona-2,6-diene (7) and 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene (8). Reaction of 15 with p-toluenesulfonic acid in refluxing cyclohexane solution gave the same two products (7 and 8) as well as a small amount of 1-benzyl-1,2-dihydronaphthalene (16). Treatment of either 15 or 16 with AlCl3 gave only 8. Treatment of 1-benzyl-2-tetralol (17) with AlCl3 also gave 8. The mechanism of formation of 7 and 8 from 15 and 16 is discussed.