5,6-Didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo<5,6>cycloocta<1,2,3,4-def>fluorene | 129000-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5,6-Didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo<5,6>cycloocta<1,2,3,4-def>fluorene
• 英文别名: 6,6,11,11-Tetramethylhexacyclo[14.4.2.05,20.07,19.010,18.012,17]docosa-1(20),2,4,7(19),8,10(18),12,14,16-nonaen-21-yne
• CAS: 129000-06-2
• 化学式: C₂₆H₂₀
• 分子量: 332.445
• InChiKey: CRQYINKIHOMQST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  5,6-Didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo<5,6>cycloocta<1,2,3,4-def>fluorene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以69%的产率得到5,6-Dihydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo<5,6>cycloocta<1,2,3,4-def>fluorene
  参考文献：
  名称：

  Arene synthesis by extrusion reaction. 16. Coplanar and stable derivatives of 13,14-didehydro-tribenzo[a,c,e]cyclooctene: synthesis of 5,6-didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione and x-ray crystal structures of 1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6-cycloocta[1,2,3,4-def]fluorene and 1,12-dihydro-1,1,12,12-tetramethyldicyclopenta[def,jkl]tetraphenylene

  摘要：

  5,6-Didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene (2) and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione (3) have been synthesized. Structural investigation of these molecules revealed that they all possess a coplanar structure.

  DOI：

  10.1021/jo00078a031
• 作为产物：
  描述：

  Dimethyl tribenzocyclooctene-1,4-dicarboxylate 在 palladium on activated charcoal 、 过氧化苯甲酰 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 potassium tert-butylate 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 17.17h， 生成 5,6-Didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo<5,6>cycloocta<1,2,3,4-def>fluorene
  参考文献：
  名称：

  Arene synthesis by extrusion reaction. 16. Coplanar and stable derivatives of 13,14-didehydro-tribenzo[a,c,e]cyclooctene: synthesis of 5,6-didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione and x-ray crystal structures of 1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6-cycloocta[1,2,3,4-def]fluorene and 1,12-dihydro-1,1,12,12-tetramethyldicyclopenta[def,jkl]tetraphenylene

  摘要：

  5,6-Didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene (2) and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione (3) have been synthesized. Structural investigation of these molecules revealed that they all possess a coplanar structure.

  DOI：

  10.1021/jo00078a031

文献信息

• A planar and stable derivative of 13,14-didehydrotribenzo[a,c,e]cyclooctene: synthesis and x-ray crystal structure of 5,6-didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene
  作者：Xiaomin Wang、Ruji Wang、Thomas C. W. Mak、Henry N. C. Wong

  DOI：10.1021/ja00177a046

  日期：1990.10

  The crystal structure consists of a packing of discrete molecules with normal van der Waals contacts, and the three independent molecules are almost perpendicular to each other (Figure 2); values of the dihedral angle between pairs of least-squares molecular planes are as follows: I-II 93.0 (9) o , II-III 77.8 (9) o , and I-III 81.4 (9) o . In conclusion, we have synthesized a stable planar derivative

  晶体结构由具有正常范德华接触的离散分子堆积组成，三个独立的分子几乎相互垂直（图 2）；最小二乘分子平面对之间的二面角值如下：I-II 93.0 (9) o 、II-III 77.8 (9) o 和I-III 81.4 (9) o 。总之，我们合成了 13,14-二脱氢三苯并 [a,c,e] 环辛烯 (1) 的稳定平面衍生物，这是苯环化的环辛三烯家族中唯一难以捉摸的成员
• WANG, XIAO-MIN;WANG, RU-JI;MAK, THOMAS C. W.;WONG, HENRY N. C., J. AMER. CHEM. SOC., 112,(1990) N1, C. 7790-7791
  作者：WANG, XIAO-MIN、WANG, RU-JI、MAK, THOMAS C. W.、WONG, HENRY N. C.

  DOI：——

  日期：——
• Arene synthesis by extrusion reaction. 16. Coplanar and stable derivatives of 13,14-didehydro-tribenzo[a,c,e]cyclooctene: synthesis of 5,6-didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione and x-ray crystal structures of 1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6-cycloocta[1,2,3,4-def]fluorene and 1,12-dihydro-1,1,12,12-tetramethyldicyclopenta[def,jkl]tetraphenylene
  作者：Xiao Min Wang、Xuelong Hou、Zhongyuan Zhou、Thomas C. W. Mak、Henry N. C. Wong

  DOI：10.1021/jo00078a031

  日期：1993.12

  5,6-Didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene (2) and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione (3) have been synthesized. Structural investigation of these molecules revealed that they all possess a coplanar structure.