9-tert-butyl-9,10-dihydroanthracene | 13387-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-tert-butyl-9,10-dihydroanthracene
• CAS: 13387-48-9
• 化学式: C₁₈H₂₀
• 分子量: 236.357
• InChiKey: RCMNLZCMGKUYFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  9-tert-butyl-9,10-dihydroanthracene 生成
  参考文献：
  名称：

  Formation of mono- and dianions of polycyclic hydrocarbons through deprotonation with the alkylithium-N,N,N',N'-tetramethylethylenediamine complex. Convenient general method of dehydrogenation

  摘要：

  DOI：

  10.1021/ja00815a023
• 作为产物：
  描述：

  9-t-butyl-9,10-dihydroanthracen-9-ol 在 三乙基硅烷 、 三氟乙酸 作用下， 生成 9-tert-butyl-9,10-dihydroanthracene
  参考文献：
  名称：

  Structural effects controlling the rate of the retro-Diels-Alder reaction in anthracene cycloadducts

  摘要：

  DOI：

  10.1021/jo00266a006

文献信息

• Proton magnetic resonance of some 9,10-dihydroanthracenes
  作者：W. Carruthers、G. E. Hall

  DOI：10.1039/j29660000861

  日期：——

  m.r.) spectrum of the 9,10-di-t-butyl compound shows that it has either a planar conformation of the central ring or the trans configuration with rapid interconversion of the two conformers. Homo-allylic coupling is observed in the n.m.r. spectra of 9-t-butyl-9,10-dihydroanthracene and 1-phenyl-1,4-dihydronaphthalene, in the latter case with a coupling constant of 6 c./sec.

  二硫代或二硫代蒽与叔丁基氯反应，得到9-叔丁基和9,10-二叔丁基-9,10-二氢蒽与一些1,4-二叔丁基的混合物-1，4-二氢蒽。9,10-二叔丁基化合物的核磁共振（nmr）谱显示，它具有中心环的平面构型或具有两个构象体快速互变的反式构型。在9，叔丁基-9，10-二氢蒽和1-苯基-1，4-二氢萘的nmr光谱中观察到均烯丙基偶联，在后者情况下，偶联常数为6℃/秒。
• Conformational analysis of 9,10-dihydroanthracenes. Molecular mechanics calculations and carbon-13 NMR
  作者：Peter W. Rabideau、Jennifer L. Mooney、Kenny B. Lipkowitz

  DOI：10.1021/ja00286a002

  日期：1986.12

  The conformational analyses of 9, 10-dihydroanthracene and several of its methylated and ethylated derivatives are studied by empirical force field calculations (MM2 and MMPI). The computational results are considered in light of previous and current carbon NMR data. Model compounds are examined which involve fixed, planar, and boat-shaped conformations about the central ring, and these /sup 13/C NMR

  通过经验力场计算（MM2 和 MMPI）研究了 9, 10-二氢蒽及其几种甲基化和乙基化衍生物的构象分析。根据以前和当前的碳 NMR 数据考虑计算结果。检查模型化合物，其中涉及围绕中心环的固定、平面和船形构象，然后将这些 /sup 13/C NMR 数据与灵活系统进行比较。得出的结论是，碳化学位移和碳氢耦合常数与分子力学计算的结果一致，这表明中心环周围的平面性比以前认为的更大。
• Lund, Torben; Lund, Henning, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 6, p. 470 - 485
  作者：Lund, Torben、Lund, Henning

  DOI：——

  日期：——
• Bogdanovic, Borislav; Janke, Nikolaus; Kinzelmann, Hans-Georg, Chemische Berichte, 1990, vol. 123, # 7, p. 1507 - 1515
  作者：Bogdanovic, Borislav、Janke, Nikolaus、Kinzelmann, Hans-Georg

  DOI：——

  日期：——
• Crystal and molecular structure of 10-substituted 9-anthracenones. Substituent size as the controlling factor for the nonplanarity of the central ring
  作者：Andrzej Sygula、Renata Sygula、Frank R. Fronczek、Peter W. Rabideau

  DOI：10.1021/jo00038a011

  日期：1992.6

  MM2 calculations for a series of 10-R-9-anthracenones demonstrate an increase of the folding of the central ring with increasing size of the substituent. All the substituents considered prefer the pseudoaxial position except fluorine, which prefers the pseudoequatorial orientation. The anthracenone moiety approaches planarity when the size of the substituents approaches the size of the hydrogen atom. The planar conformation for 9-anthracenone is also shown by vibrational frequency calculations to be a true potential energy minimum at the ab initio 3-21G level. X-ray structure determination shows that 10-R-9-anthracenones (R = Me, iPr, tBu, Ph, and Br) generally exhibit the structural features predicted by MM2 calculations for the isolated molecules. However, 10-Me and 10-Ph-9-anthracenones are found to be significantly less folded than calculated by MM2, the discrepancy being attributed to the crystal packing forces. Consideration of the theoretical as well as the experimental results leads to the conclusion that the parent 9-anthracenone is expected to be planar in the crystal state.