cis-12b,12c-dimethyl-12b,12c-dihydrodibenzoperylene | 81715-66-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: cis-12b,12c-dimethyl-12b,12c-dihydrodibenzoperylene
• CAS: 81715-66-4
• 化学式: C₂₈H₂₀
• 分子量: 356.467
• InChiKey: KTTNLVNHVKZSOA-HNRBIFIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  28.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  cis-12b,12c-dimethyl-4,5,12b,12c,14,15-hexahydrodibenzoperylene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 2.0h， 以28%的产率得到cis-12b,12c-dimethyl-12b,12c-dihydrodibenzoperylene
  参考文献：
  名称：

  An Experimental Estimation of Aromaticity Relative to That of Benzene. The Synthesis and NMR Properties of a Series of Highly Annelated Dimethyldihydropyrenes: Bridged Benzannulenes

  摘要：

  The synthesis of 13 trans-dimethyldihydropyrenes (bridged [14]annulenes) fused to one or more benzene, naphthalene, phenanthrene, phenalene, or quinoxaline rings and 6 cis-dihydropyrene derivatives from benzenoid precursors using either a thiacyclophane route or an electrocyclic addition of a furan to an annulyne followed by deoxygenation is reported. Their H-1 NMR spectra are studied in detail to obtain correlations between (3)J(H,H) coupling constants and the internal methyl proton chemical shifts and also between the latter and the more distant external annulene ring proton shifts. These linear correlations are then used to obtain a relationship between the relative aromaticity of benzene and the fused ring in question, such that the aromaticity of the fused ring can be estimated relative to that of a benzene ring simply from a measurement of chemical shift in the fused annulene.

  DOI：

  10.1021/ja00110a008

文献信息

• Synthesis of diatropic highly benzannelated annulenes.
  作者：Reginald H Mitchell、Ramanathan Mahadevan

  DOI：10.1016/s0040-4039(01)92439-6

  日期：1981.1

  The first examples of annelated cis-dihydropyrenes, 16, 18, 19, together with a number of highly annelated trans-dihydropyrenes, 2 - 4 and, 17, are described. All are diatropic and indicate that higher annelation does not remove the delocalisation in a macrocyclic ring.

  稠合的第一实施例的顺-dihydropyrenes，16，18，19，与多个高度稠合在一起的反式-dihydropyrenes，2 - 4和，17，进行说明。所有这些都是亲核的，表明较高的成环作用并不能消除大环中的离域。