12,13-dihydro-5H-indolo[3,2-c]acridine | 209268-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 12,13-dihydro-5H-indolo[3,2-c]acridine
• 英文别名: 6,13-dihydro-5H-indolo[3,2-c]acridine；6,13-dihydro-5H-indolo[3,2-c]acridine；6,13-Dihydro-5H-indolo[3,2-c]acridin
• CAS: 209268-82-6
• 化学式: C₁₉H₁₄N₂
• 分子量: 270.334
• InChiKey: WGGKDCQBVFJRLU-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C
• 沸点：
  526.9±30.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  12,13-dihydro-5H-indolo[3,2-c]acridine 在 ammonium hydroxide 、 sodium acetate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.17h， 生成 12-Methyl-5,6-dihydroindolo[3,2-c]acridine
  参考文献：
  名称：

  Preparation and Study of Tautomers Derived from 2-(2‘-Pyridyl)indole and Related Compounds

  摘要：

  Methylation of 2-(2'-pyridyl)indole provides the corresponding N-methylated salt that undergoes deprotonation with mild base to provide the tautomeric (E)-1-methyl-2-(2'-indolenylidene)-1,2-dihydropyridine, whose geometry is established through a NOE experiment. Bridging at the 3,3'-positions leads to tautomers having the opposite stereochemistry. A benzo-fused analogue exhibits similar behavior as does 2-(2'-quinolinyl)pyrrole. The importance of the connectivity to pyridine is examined by considering three possible regioisomers, only two of which show tautomeric behavior. The tautomers show strong solvatochromic dependence and good linear behavior. The indoles absorb at shorter wavelengths and are strongly emitting while the tautomers show a strong bathochromic shift and emit only weakly; the salts exhibit intermediate behavior. NMR properties are consistent with contributions from a dipolar and uncharged resonance form while MO calculations indicate that the indole is about 40 kcal/mol more stable than its tautomer.

  DOI：

  10.1021/jo980134j
• 作为产物：
  描述：

  (1,2,3,4-tetrahydro-acridin-4-yl)-glyoxylic acid ethyl ester 在 吡啶 、 盐酸 作用下， 生成 12,13-dihydro-5H-indolo[3,2-c]acridine
  参考文献：
  名称：

  Borsche; Manteuffel, Justus Liebigs Annalen der Chemie, 1938, vol. 534, p. 56,62

  摘要：

  DOI：

文献信息

• Combined effect of hydrogen bonding interactions and freezing of rotameric equilibrium on the enhancement of photostability
  作者：Barbara Golec、Krzysztof Nawara、Alexandr Gorski、Randolph P. Thummel、Jerzy Herbich、Jacek Waluk

  DOI：10.1039/c8cp00726h

  日期：——

  which can exist only in the syn form, is more photostable in alcohols than similar, but non-rigid molecules. This additional photostability enhancement is due to the elimination of a slower channel of excited state deactivation in alcohol complexes, S0 ← S1 internal conversion. The dominant, faster channel of S1 depopulation is the excited state double proton transfer, manifested by the presence of low

  12,13-dihydro-5 H-吲哚并[3,2- c ] ac啶（IA）是一种具有质子给体/受体官能团的刚性双官能吲哚衍生物，其光物理性质和光稳定性可被环境急剧改变。与醇形成氢键导致三重态形成效率的显着降低和光稳定性的提高。光降解产率被发现是大约200倍降低的甲醇和1-丙醇比Ñ正己烷或乙腈。已经报道了两种吲哚-萘啶核苷的相似作用，它们可以以顺式和反式的形式存在。我们证明了IA只能以合成形式存在的，在醇中的光稳定性高于类似但非刚性的分子。这种额外的光稳定性增强是由于消除了醇配合物中S 0 ←S 1内部转化的较慢的激发态失活通道。S 1减少的主要，较快的通道是激发态双质子转移，表现为低能互变异构荧光的存在。
• Preparation and Study of Tautomers Derived from 2-(2‘-Pyridyl)indole and Related Compounds
  作者：Feiyue Wu、Jon Hardesty、Randolph P. Thummel

  DOI：10.1021/jo980134j

  日期：1998.6.1

  Methylation of 2-(2'-pyridyl)indole provides the corresponding N-methylated salt that undergoes deprotonation with mild base to provide the tautomeric (E)-1-methyl-2-(2'-indolenylidene)-1,2-dihydropyridine, whose geometry is established through a NOE experiment. Bridging at the 3,3'-positions leads to tautomers having the opposite stereochemistry. A benzo-fused analogue exhibits similar behavior as does 2-(2'-quinolinyl)pyrrole. The importance of the connectivity to pyridine is examined by considering three possible regioisomers, only two of which show tautomeric behavior. The tautomers show strong solvatochromic dependence and good linear behavior. The indoles absorb at shorter wavelengths and are strongly emitting while the tautomers show a strong bathochromic shift and emit only weakly; the salts exhibit intermediate behavior. NMR properties are consistent with contributions from a dipolar and uncharged resonance form while MO calculations indicate that the indole is about 40 kcal/mol more stable than its tautomer.
• Borsche; Manteuffel, Justus Liebigs Annalen der Chemie, 1938, vol. 534, p. 56,62
  作者：Borsche、Manteuffel

  DOI：——

  日期：——