5-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline

• 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: 5-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline
• 英文别名: 5-methoxy-2,2,4-trimethyl-1H-quinoline
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: OUXHGROLLOYRIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  四氰基乙烯 、 5-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline 在 正丁基锂 作用下， 生成 5-methoxy-3,4-(2',2',3',3'-tetracyanocyclobutano)-1,2-dihydro-2,2,4-trimethylquinoline
  参考文献：
  名称：

  Substitution Reaction of Tetracyanoethylene with Acetone-Anils

  摘要：

  AbstractThe products from the condensation of acetone‐anils (1) and TCNE reaction were characterized after separation. The main products, tricyanoethylene derivatives (7–9) were isolated with the malonodinitrile derivatives (10–12), respectively. The [2+2] cycloaddition product (13), namely 5‐methoxy‐3,4‐(2′,2′,3′,3′‐tetracyanocyclobutano)‐l,2‐dihydro‐2,2,4‐trimethylquinoline also has been isolated. The distribution of these three products is substituent dependent.

  DOI：

  10.1002/jccs.199600073
• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 、 间氨基苯甲醚 在 lithium carbonate 、 magnesium bromide 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以48%的产率得到7-甲氧基-2,2,4-三甲基-1,2-二氢喹啉
  参考文献：
  名称：

  无溶剂MgBr 2催化多组分反应区域选择性合成1，2-二氢喹啉

  摘要：

  描述了通过苯胺和两个酮之间的多组分反应的1，2-二氢喹啉的高效和区域选择性合成。该反应用溴化镁催化，并在无溶剂的条件下进行。当通过使用3-取代的苯胺和非对称取代的酮进行反应时，在四种预期的区域异构体中主要发现单一产物。对包括环酮在内的各种苯胺和酮进行了评估，从而提供了一系列具有不同取代方式的1,2-二氢喹啉。讨论了该机制的研究。有证据表明，在环化杂环之前，由于苯胺和一种酮之间的反应而导致亚胺的原位形成。

  DOI：

  10.1021/jo400973g

文献信息

• Efficient Green Coumarin Dopants for Organic Light-Emitting Devices
  作者：Meng-Ting Lee、Chia-Kuo Yen、Wen-Ping Yang、Hsian-Hung Chen、Chi-Hung Liao、Chih-Hung Tsai、Chin H. Chen

  DOI：10.1021/ol049903d

  日期：2004.4.1

  [GRAPHICS]We have synthesized a new green fluorescent dopant C-545P having incorporated five strategically placed "methyl" steric spacers on the julolidyl ring system. C-545P has good thermal properties and photostability, and when fabricated as a dopant in an Alq(3)-hosted OLED device, it shows notable improvement in luminance efficiency and is more resistant to concentration quenching than C-545T, particularly in the doping concentration range between 1 and 2% v/v, while achieving comparable device stability.
• Regioselective Synthesis of 1,2-Dihydroquinolines by a Solvent-Free MgBr₂-Catalyzed Multicomponent Reaction
  作者：Rsuini U. Gutiérrez、Hans C. Correa、Rafael Bautista、José Luis Vargas、Alberto V. Jerezano、Francisco Delgado、Joaquín Tamariz

  DOI：10.1021/jo400973g

  日期：2013.10.4

  two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of

  描述了通过苯胺和两个酮之间的多组分反应的1，2-二氢喹啉的高效和区域选择性合成。该反应用溴化镁催化，并在无溶剂的条件下进行。当通过使用3-取代的苯胺和非对称取代的酮进行反应时，在四种预期的区域异构体中主要发现单一产物。对包括环酮在内的各种苯胺和酮进行了评估，从而提供了一系列具有不同取代方式的1,2-二氢喹啉。讨论了该机制的研究。有证据表明，在环化杂环之前，由于苯胺和一种酮之间的反应而导致亚胺的原位形成。
• Substitution Reaction of Tetracyanoethylene with Acetone-Anils
  作者：Wen-Chung Lin、Shing-Ting Huang、Shaw-Tao Lin

  DOI：10.1002/jccs.199600073

  日期：1996.12

  AbstractThe products from the condensation of acetone‐anils (1) and TCNE reaction were characterized after separation. The main products, tricyanoethylene derivatives (7–9) were isolated with the malonodinitrile derivatives (10–12), respectively. The [2+2] cycloaddition product (13), namely 5‐methoxy‐3,4‐(2′,2′,3′,3′‐tetracyanocyclobutano)‐l,2‐dihydro‐2,2,4‐trimethylquinoline also has been isolated. The distribution of these three products is substituent dependent.