2,6-di-tert-butyl-1,4-benzoquinone-4-N-(8-acetylamino-1-naphthyl)imine | 137438-59-6

• 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-1,4-benzoquinone-4-N-(8-acetylamino-1-naphthyl)imine
• 英文别名: N-[8-[(3,5-ditert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)amino]naphthalen-1-yl]acetamide
• CAS: 137438-59-6
• 化学式: C₂₆H₃₀N₂O₂
• 分子量: 402.536
• InChiKey: YXRMABUBODATIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  乙酸酐 、 2,3-Dihydroperimidine-2-spiro-1'(3,5-di-tert-butyl-2,5-cyclohexadien-4-one) 反应 0.08h， 以92%的产率得到2,6-di-tert-butyl-1,4-benzoquinone-4-N-(8-acetylamino-1-naphthyl)imine
  参考文献：
  名称：

  Synthesis and structure of 2,6-di-tert-butyl-1,4-benzoquinone-4N-(8-tosylamino-1-naphthyl) imine

  摘要：

  The structure of 2,6-di-tert-butyl-1,4-benzoquinone-4-N-(8-tosylamino-1-naphthyl)imine (IId) has been studied as a model for the open form of thermo- and photochromic compounds in the cyclohexadienoneperimidine series (I), in which rearrangement occurs due to C(spiro)-N bond cleavage and N --> N proton transfer upon thermal or photoexcitation. Introduction of a bulky, electron-withdrawing tosyl substituent to the nitrogen atom stabilizes the open quinoneimine form, both in the crystalline state and in solution. The cyclohexadienone fragment is nonplanar and exists in a "boat" configuration. The open quinoneimine structure is retained upon replacement of the tosyl substituent by a less bulky electron-withdrawing acetyl substituent, suggesting that electronic factors are decisive in formation of the open structure.

  DOI：

  10.1007/bf01172258