2,3:6,7-dibenzobicyclo<3.2.2>nona-2,6-diene | 23417-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 2,3:6,7-dibenzobicyclo<3.2.2>nona-2,6-diene
• 英文别名: Tetracyclo[7.6.2.02,7.010,15]heptadeca-2,4,6,10,12,14-hexaene
• CAS: 23417-01-8
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: GSTYKFXFCDZPMB-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C(Solv: methanol (67-56-1))
• 沸点：
  332.7±27.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• 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：

  5-benzyl-5-phenyl-dihydro-furan-2-one 在 sodium tetrahydroborate 、 硫酸 、 氢碘酸 、 溶剂黄146 作用下， 以 甲醇 、 xylene 为溶剂， 反应 15.67h， 生成 2,3:6,7-dibenzobicyclo<3.2.2>nona-2,6-diene
  参考文献：
  名称：

  Cyclialkylation studies. 1. A practical synthetic approach to the 2,3:6,7-dibenzobicyclo[3.2.2]nona-2,6-diene system

  摘要：

  DOI：

  10.1021/jo00008a070

文献信息

• Clear cut example of preference for a 6-membered ring radical cyclisation over the homologous 5-membered ring radical cyclisation. The reaction of 5-[bromoalkyl]-5H-dibenzo[a,d]cycloheptenes with Bu3SnH
  作者：C. Hada、M.D. Banciu、J.-M. Mattalia、M. Chanon

  DOI：10.1016/0040-4039(96)00695-8

  日期：1996.5

  The radical cyclisation reaction of the 5-[2-bromo-ethyl]-5H-dibenzo[a,d]cycloheptene 4 with Bu3SnH and AIBN led to the cyclised hydrocarbon 5 as major product, whereas the bromo-derivative 8 with Bu3SnH and AIBN gave only the straight chain product 9. An explanation based on the conformational rigidity of dibenzo[a,d]cycloheptene system calculated by AM1 method is proposed.

  5- [2-溴-乙基] -5H-二苯并[ a，d ]环庚烯4与Bu 3 SnH和AIBN的自由基环化反应导致环化烃5为主要产物，而溴代衍生物8与Bu 3 SnH和AIBN仅给出了直链产物9。提出了基于AM1法计算的二苯并[ a，d ]环庚烯体系的构象刚度的解释。
• New friedel-crafts chemistry. XXX. Acid-catalyzed cyclodehydration of some 4-benzyl-1-tetralols and 4-phenylalkanols. Rearrangement of dibenzobicyclo[3.2.2]nona-2,6-diene by aluminum chloride
  作者：Chow-Eng Low、Royston M. Roberts

  DOI：10.1021/jo00950a026

  日期：1973.5
• 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.