trans-2-[2,6-bis(hydroxymethyl)phenyl]-10b,10c-dimethyl-10b,10c-dihydropyrene | 640734-40-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: trans-2-[2,6-bis(hydroxymethyl)phenyl]-10b,10c-dimethyl-10b,10c-dihydropyrene
• CAS: 640734-40-3
• 化学式: C₂₆H₂₄O₂
• 分子量: 368.475
• InChiKey: GFLYHLLGPRPYOM-DIVCQZSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-2-[2,6-bis(hydroxymethyl)phenyl]-10b,10c-dimethyl-10b,10c-dihydropyrene 在 氢氧化钾 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 20.0h， 生成 anti-9-methyl-18-trans-2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)-2,11-dithia[3,3]metacyclophane
  参考文献：
  名称：

  Evidence for Homo-Conjugation between Two Revolving 14π-Electron Systems in 10b-Methyl-10c-[2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)]-10b,10c-dihydropyrene

  摘要：

  Ring contraction followed by an elimination reaction on anti-9-methyl-18-trans-2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)-2,11-dithia[3,3]metacyclophane gave the desired compound 10b-methyl-10c-[2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)]-10b,10c-dihydropyrene. 1H NMR spectroscopic analysis indicated a ring current effect over a considerable distance from the macro-molecular plane of each of the aromatic rings with the two pi systems freely rotating. Bathochromic shifts and peak broadening in its electronic spectrum clearly supports the presence of through-space pi-pi interactions between the two aromatic rings. This should serve as a good model to verify homo-conjugation effect in such a novel system where the two pi systems are freely revolving.

  DOI：

  10.1021/ja0382260
• 作为产物：
  描述：

  2,6-二氯苯胺 在 sodium tetrahydroborate 、 硫酸 、 二异丁基氢化铝 、 sodium nitrite 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 正己烷 、 苯 为溶剂， 反应 7.84h， 生成 trans-2-[2,6-bis(hydroxymethyl)phenyl]-10b,10c-dimethyl-10b,10c-dihydropyrene
  参考文献：
  名称：

  Evidence for Homo-Conjugation between Two Revolving 14π-Electron Systems in 10b-Methyl-10c-[2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)]-10b,10c-dihydropyrene

  摘要：

  Ring contraction followed by an elimination reaction on anti-9-methyl-18-trans-2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)-2,11-dithia[3,3]metacyclophane gave the desired compound 10b-methyl-10c-[2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)]-10b,10c-dihydropyrene. 1H NMR spectroscopic analysis indicated a ring current effect over a considerable distance from the macro-molecular plane of each of the aromatic rings with the two pi systems freely rotating. Bathochromic shifts and peak broadening in its electronic spectrum clearly supports the presence of through-space pi-pi interactions between the two aromatic rings. This should serve as a good model to verify homo-conjugation effect in such a novel system where the two pi systems are freely revolving.

  DOI：

  10.1021/ja0382260