6-甲基-4-(7-甲基-3,4-二氢萘-1-基)-1,2-二氢萘 | 7499-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-甲基-4-(7-甲基-3,4-二氢萘-1-基)-1,2-二氢萘
• 英文名称: 7,7'-Dimethyl-3,4,3',4'-tetrahydro-[1,1']binaphthyl
• 英文别名: 7,7'-Dimethyl-3,4,3',4'-tetrahydro-<1,1'>binaphthyl；3,4,3',4'-Tetrahydro-7,7'-dimethyl-binaphthyl-(1,1')；7,7'-Dimethyl-3,3',4,4'-tetrahydro-1,1'-binaphthalene；6-methyl-4-(7-methyl-3,4-dihydronaphthalen-1-yl)-1,2-dihydronaphthalene
• CAS: 7499-37-8
• 化学式: C₂₂H₂₂
• 分子量: 286.417
• InChiKey: BQUYZPVKCWPYQT-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111.6 °C
• 沸点：
  426.1±40.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  6-甲基-4-(7-甲基-3,4-二氢萘-1-基)-1,2-二氢萘 在 lead(IV) acetate 、 palladium on activated charcoal 、 乙酸酐 、 溶剂黄146 、 xylene 作用下， 生成 9,12-dimethyl-dibenzo[c,g]phenanthrene-3,4-dicarboxylic acid-anhydride
  参考文献：
  名称：

  A New Synthesis of Coronene

  摘要：

  DOI：

  10.1021/ja01864a014
• 作为产物：
  描述：

  7-甲基-3,4-二氢-2H-1-萘酮 在 乙醇 、 aluminium amalgam 、 苯 作用下， 生成 6-甲基-4-(7-甲基-3,4-二氢萘-1-基)-1,2-二氢萘
  参考文献：
  名称：

  A New Synthesis of Coronene

  摘要：

  DOI：

  10.1021/ja01864a014

文献信息

• The conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9-(1,2-dihydro-6-R-naphthalen-4-yl)-2-R-5H-benzo[7]annulene, the question of atropisomerism versus ring inversion
  作者：Parviz Rashidi Ranjbar、Hamid Roshan

  DOI：10.3998/ark.5550190.0011.905

  日期：——

  Conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9-(1,2-dihydro-naphthalen-4-yl)-5H-benzo[7]annulene 1 are observed at room temperature in solution. Two conformational processes are possible in 1, i.e. atropisomerism around the sp(2)-sp(2) pivot bond and ring inversion of cycloheptadiene moiety which together provide four minima structures. The (3)J calculation by Haasnoot equation on optimized structures is accordance with the 7-substituents in pseudo equatorial (exo) position in both forms. The barrier to conformational process is determined by dynamic H-1-NMR spectroscopy to be Delta G(not equal) ((365K))=74.5+/-0.5 kJ/mol. Solvent dependent populations of the two forms are studied in DMSO-d(6) and CDCl3, the population ratio is not sensitive to solvent polarity.
• The marked difference in conformational behavior of the two diastereomers of 7-substituted-1,1-dichloro-7b-((Z)-8-chloro-6,7-dihydro-5H-benzo[7]annulen-9-yl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene, single crystal X-ray, 1H NMR and AM1 studies
  作者：Hamid Roshan、Parviz Rashidi-Ranjbar

  DOI：10.1016/j.molstruc.2010.06.037

  日期：2010.9

  The 7-substituted of 1 and 2 were synthesized and conformational analysis carried out. While 7-substituted of 2 show two conformers in solution, 7-substituted of 1 show only one form in solution. AM1 semi-empirical molecular orbital calculations show that the conformation of cycloheptadiene ring in 1 and 2 is a twist boat form. In this conformation, the C-7 substituents can be oriented in pseudo equatorial (exo) and pseudo axial (endo) positions. The (3)J calculation with Haasnoot equation on optimized structure of 2 reproduces the observed 3J coupling constants in exo and endo forms. Ring inversion of cycloheptadiene moiety in substituted 2 interconvert the e'-a' (exo-endo) positions. The (3)J calculation on optimized structure of 1 shows that 7-substitution is in pseudo equatorial (exo) direction, as found in the crystal structure of la by single crystal X-ray crystallography. The barrier to ring inversion in 2a is determined by dynamic H-1 NMR spectroscopy to be Delta(not equal)G((335K)) = 68.0 +/- 0.5 kj/mol. (C) 2010 Elsevier B.V. All rights reserved.
• Two Cases of Unexpected Formation of the Fluoranthene System
  作者：Ernst D. Bergmann、Perez Bracha、Jochanan Blum、Meir Engelrath

  DOI：10.1021/jo01033a519

  日期：1964.10
• 448. A synthesis of benzo[j]fluoranthene and its derivatives, using palladium–sulphur as a cyclodehydrogenating agent
  作者：Malcolm Crawford、V. R. Supanekar

  DOI：10.1039/jr9640002380

  日期：——
• Sen Gupta,S.C. et al., Journal of the Indian Chemical Society, 1960, vol. 37, # 10, p. 597 - 602
  作者：Sen Gupta,S.C. et al.

  DOI：——

  日期：——