13H-13-dibenzofluorene | 216393-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 13H-13-dibenzofluorene
• 英文别名: 12-(Dinaphthalen-1-ylmethyl)pentacyclo[11.8.0.02,11.05,10.014,19]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene
• CAS: 216393-39-4
• 化学式: C₄₂H₂₈
• 分子量: 532.684
• InChiKey: MCVGILOLUUTCJF-UHFFFAOYSA-N

物化性质

• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  13H-13-dibenzofluorene 在 三氯化铝 作用下， 以 苯 为溶剂， 以15%的产率得到二苯基甲烷
  参考文献：
  名称：

  On the Di-1-naphthylcarbene−Dibenzofluorene Rearrangement and the Ethylenization of Diarylcarbinols

  摘要：

  Solution-spray flash vacuum thermolysis of di-1-naphthyldiazomethane (9) results in the formation of dibenzo[c,g]fluorene (12), formed via a carbene-carbene rearrangement of di-1-naphthylcarbene (10), The isomeric dibenzo[a,i]fluorene (11) claimed by Franzen and Joschek (Liebigs Ann. Chem. 1960, 633, 7) is not formed, and no dibenzofluorene is formed on thermolysis in boiling naphthalene. 11 is formed on dehydration of di-1-naphthylcarbinol (14) with phosphoric acid, but the claimed tetra-1-naphthylethylene (13) is not formed, and the so-called ethylenization of diarylcarbinols is cast in doubt generally. The compound previously believed to be 13 is 13-[di(1-naphthyl)methyl]-dibenzo[a,i]fluorene (22). The alleged cleavage of 13 into two molecules of carbene 10 is unsubstantiated.

  DOI：

  10.1021/jo981397g
• 作为产物：
  描述：

  二-1-萘甲醇 在 磷酸 作用下， 200.0 ℃ 、200.0 Pa 条件下， 反应 2.0h， 以24%的产率得到二(5-甲氧基-2-{[(4-甲氧基-3,5-二甲基吡啶-2-基)甲基]亚硫酰基<亚磺酰>}苯并咪唑-1-化)二水合物镁
  参考文献：
  名称：

  On the Di-1-naphthylcarbene−Dibenzofluorene Rearrangement and the Ethylenization of Diarylcarbinols

  摘要：

  Solution-spray flash vacuum thermolysis of di-1-naphthyldiazomethane (9) results in the formation of dibenzo[c,g]fluorene (12), formed via a carbene-carbene rearrangement of di-1-naphthylcarbene (10), The isomeric dibenzo[a,i]fluorene (11) claimed by Franzen and Joschek (Liebigs Ann. Chem. 1960, 633, 7) is not formed, and no dibenzofluorene is formed on thermolysis in boiling naphthalene. 11 is formed on dehydration of di-1-naphthylcarbinol (14) with phosphoric acid, but the claimed tetra-1-naphthylethylene (13) is not formed, and the so-called ethylenization of diarylcarbinols is cast in doubt generally. The compound previously believed to be 13 is 13-[di(1-naphthyl)methyl]-dibenzo[a,i]fluorene (22). The alleged cleavage of 13 into two molecules of carbene 10 is unsubstantiated.

  DOI：

  10.1021/jo981397g

文献信息

• On the Di-1-naphthylcarbene−Dibenzofluorene Rearrangement and the Ethylenization of Diarylcarbinols
  作者：Michèle Régimbald-Krnel、Curt Wentrup

  DOI：10.1021/jo981397g

  日期：1998.11.1

  Solution-spray flash vacuum thermolysis of di-1-naphthyldiazomethane (9) results in the formation of dibenzo[c,g]fluorene (12), formed via a carbene-carbene rearrangement of di-1-naphthylcarbene (10), The isomeric dibenzo[a,i]fluorene (11) claimed by Franzen and Joschek (Liebigs Ann. Chem. 1960, 633, 7) is not formed, and no dibenzofluorene is formed on thermolysis in boiling naphthalene. 11 is formed on dehydration of di-1-naphthylcarbinol (14) with phosphoric acid, but the claimed tetra-1-naphthylethylene (13) is not formed, and the so-called ethylenization of diarylcarbinols is cast in doubt generally. The compound previously believed to be 13 is 13-[di(1-naphthyl)methyl]-dibenzo[a,i]fluorene (22). The alleged cleavage of 13 into two molecules of carbene 10 is unsubstantiated.