2,3-Trimethylenebenzoquinoline

• 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: 2,3-Trimethylenebenzoquinoline
• 英文别名: 11-Azatetracyclo[8.7.0.03,8.012,16]heptadeca-1,3,5,7,9,11,16-heptaene
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: KXJFEXZUICMVSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 盐酸 、 manganese(IV) oxide 、 氢氧化钾 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 硫酸 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 93.0h， 生成 2,3-Trimethylenebenzoquinoline
  参考文献：
  名称：

  Synthesis and Properties of Ligands Based on Benzo[g]quinoline

  摘要：

  The preparation of 3-amino-2-naphthaldehyde is described. Ammonolysis of 3-hydroxy-8-naphthoic acid affords the corresponding amino acid which can be esterified and then reduced with LAH. Protection of the amino group, MnO2 oxidation of the primary alcohol to an aldehyde, and deprotection gave the amino aldehyde which is an excellent Friedlander synthon for benzo[g]quinolines. Dimethylene-bridged analogues of 2,2'-bipyridine and 2,2';6,2''-terpyridine were prepared as well as orthocyclophanes derived from tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione (TCU-2,7-dione). The absorption and emission spectra of these species are consistent with the parent benzo[g]quinoline where bathochromic shifts result from increased delocalization. The TCU derivative evidences exciplex formation so that its benzo[g]quinoline emission is almost completely quenched and an exciplex emission appears at 525 nm. Electrochemical analysis indicates that both reduction and UV absorption involve the same pi(*) orbital.

  DOI：

  10.1021/jo00083a024

文献信息

• Synthesis and Properties of Ligands Based on Benzo[g]quinoline
  作者：Emmanuelle Taffarel、Sarah Chirayil、Randolph P. Thummel

  DOI：10.1021/jo00083a024

  日期：1994.2

  The preparation of 3-amino-2-naphthaldehyde is described. Ammonolysis of 3-hydroxy-8-naphthoic acid affords the corresponding amino acid which can be esterified and then reduced with LAH. Protection of the amino group, MnO2 oxidation of the primary alcohol to an aldehyde, and deprotection gave the amino aldehyde which is an excellent Friedlander synthon for benzo[g]quinolines. Dimethylene-bridged analogues of 2,2'-bipyridine and 2,2';6,2''-terpyridine were prepared as well as orthocyclophanes derived from tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione (TCU-2,7-dione). The absorption and emission spectra of these species are consistent with the parent benzo[g]quinoline where bathochromic shifts result from increased delocalization. The TCU derivative evidences exciplex formation so that its benzo[g]quinoline emission is almost completely quenched and an exciplex emission appears at 525 nm. Electrochemical analysis indicates that both reduction and UV absorption involve the same pi(*) orbital.