2,6-Di-tert-butyl-4-(8-isobutylamino-naphthalen-1-ylimino)-cyclohexa-2,5-dienone | 120570-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-Di-tert-butyl-4-(8-isobutylamino-naphthalen-1-ylimino)-cyclohexa-2,5-dienone
• 英文别名: 2,6-ditert-butyl-4-[8-(2-methylpropylamino)naphthalen-1-yl]iminocyclohexa-2,5-dien-1-one
• CAS: 120570-53-8
• 化学式: C₂₈H₃₆N₂O
• 分子量: 416.607
• InChiKey: SKHYXSMTPYHVLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,6-Di-tert-butyl-4-(8-isobutylamino-naphthalen-1-ylimino)-cyclohexa-2,5-dienone 生成 1-Isobutyl-2,3-dihydro-2-spiro-(4-2,6-di-tert-butyl-2,5-cyclohexadienone)perimidine
  参考文献：
  名称：

  KOMISSAROV, V. N.;XARLANOV, V. A.;UXIN, L. YU.;MINKIN, V. I., DOKL. AN CCCP, 301,(1988) N 4, S. 902-905

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Isobutyl-2,3-dihydro-2-spiro-(4-2,6-di-tert-butyl-2,5-cyclohexadienone)perimidine 以 正辛烷 为溶剂， 生成 2,6-Di-tert-butyl-4-(8-isobutylamino-naphthalen-1-ylimino)-cyclohexa-2,5-dienone
  参考文献：
  名称：

  Kharlanov, V. A.; Knyazhanskii, M. I.; Kuznetsov, V. E., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 5.2, p. 855 - 858

  摘要：

  DOI：

文献信息

• Synthesis, structure and properties of perimidine spirans
  作者：S. M. Aldoshin、M. A. Novozhilova、L. O. Atovmyan、V. N. Komissarov、V. A. Kharlanov、L. Yu. Ukhin、V. I. Minkin

  DOI：10.1007/bf00958007

  日期：1991.3

  A study was carried out on a new class of photo- and thermochromic spirocyclic cyclohexadienoneperimidines and 4H-naphtholinoneperimidines. The structures of two of these compounds were determined. The lengths of the C(spiro)-N bonds were found to be unequivalent; one of these bonds is cleaved in the photo- and thermochromic transformations. The nitrogen atom of the perimidine ring in both compounds was found to have pyramidal configuration with cis arrangement of the unshared electron pairs, while the cyclohexadienone fragments are strongly distorted toward the boat conformation. The nature of the dependence of the photo- and thermochromic properties on their structure and solvent was established.
• ——
  作者：V. A. Kharlanov

  DOI：10.1023/a:1012405229637

  日期：——

  Thermodynamic equilibrium between the spirane and quinonimine structures of photochromic perimidine derivatives was studied by electron absorption spectroscopy and semiempirical quantum-chemical methods (AM1 and PM3). The experimental data showed that the reaction entropy DeltaS(0) in octane weakly depends on the substituent structure (0.015-0.024 kJ mol(-1) K-1) and that the enthalpy of the reaction for the compound with bulky isobutyl substituent (DeltaH(0) = 7.1 kJ/mol) is lower than for those containing hydrogen and methyl group (12.9 and 13.1 kJ/mol, respectively). According to the calculations, in the spirane structure the orientation of lone electron pairs on the perimidine nitrogen atoms may be both cisoid or transoid for different orientations of the cyclohexadiene fragment which adopts a boat conformation. The quinonimine isomer can also exist in different stable conformations.