1-allyl-1,2,3,4-tetrahydroquinoline-8-carbaldehyde | 849936-12-5

• 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: 1-allyl-1,2,3,4-tetrahydroquinoline-8-carbaldehyde
• 英文别名: 1-prop-2-enyl-3,4-dihydro-2H-quinoline-8-carbaldehyde
• CAS: 849936-12-5
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: PEKUEAAOUWKYTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-allyl-1,2,3,4-tetrahydroquinoline-8-carbaldehyde 在 哌啶 、 苯甲酸 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 2.0h， 生成 dimethyl 3-vinyljulolidine-2,2-dicarboxylate
  参考文献：
  名称：

  1,5-Hydride-Shift-Triggered Cyclization for the Synthesis of Unsymmetric Julolidines

  摘要：

  直接可访问的8-取代四氢喹啉在钪(III)三氟甲磺酸催化下发生1,5-氢移位引发的环化反应，以产生难以获得的苯并喹啉衍生物，收率为21-98%。此外，突出了该反应的范围、几种后续转化以及在优化条件过程中发现的一个显著的副反应过程。

  DOI：

  10.1055/a-1559-2728
• 作为产物：
  描述：

  8-(2-Chloro-ethyl)-1,2,3,4-tetrahydro-quinoline 在 异氰环已烷 、 TEA 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-allyl-1,2,3,4-tetrahydroquinoline-8-carbaldehyde
  参考文献：
  名称：

  Investigations concerning the organolanthanide and group 3 metallocene-catalyzed cyclization–functionalization of nitrogen-containing dienes

  摘要：

  Organolanthanide catalyzed cyclization-silylation of nitrogen-containing polyunsaturated systems allows access to core structures commonly found in naturally occurring alkaloids. Nitrogen-containing dienes with various substitution patterns were investigated. The method was most successful for substrates with terminal alkenes. Cyclization upon pendant 1,1-disubstituted olefins was not realized under various conditions. Interestingly, sterically hindered sulfonamides, which were previously believed to render the catalyst inactive, were actually compatible with the catalyst, thus affording the cyclized products after prolonged reaction times. Variations using fused ring systems were also investigated. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.048

文献信息

• US6734193B1
  申请人：——

  公开号：US6734193B1

  公开（公告）日：2004-05-11
• [EN] (1,2,3,4-TETRAHYDROQUINOLIN-8-YL)-HEPTATRIENOIC ACID DERIVATIVES HAVING SERUM GLUCOSE REDUCING ACTIVITY<br/>[FR] DERIVES D'ACIDE (1,2,3,4-TETRAHYDROQUINOLIN-8-YL)-HEPTATRIENOIQUE A ACTIVITE DE REDUCTION DU GLUCOSE DU SERUM
  申请人：ALLERGAN INC

  公开号：WO2004108678A1

  公开（公告）日：2004-12-16

  Compounds of the formula (I) where the variables have the meaning defined in the specification are capable of reducing serum glucose levels in diabetic mammals without the undesirable side effects of reducing serum thyroxine levels and transiently increasing triglyceride levels.
• 1,5-Hydride-Shift-Triggered Cyclization for the Synthesis of Unsymmetric Julolidines
  作者：Andrey A. Mikhaylov、Vasilissa V. Shirokova、Viktoria A. Ikonnikova、Pavel N. Solyev、Vladislav A. Lushpa、Alexander A. Korlyukov、Alexander D. Volodin、Nadezhda S. Baleeva、Mikhail S. Baranov

  DOI：10.1055/a-1559-2728

  日期：2021.12

  Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride-shift-triggered cyclization to provide difficult to access julolidine derivatives in yields of 21–98% under scandium(III) triflate catalysis. Additionally, the scope of the reaction, several follow-up transformations and a remarkable side process discovered during optimization of the conditions are highlighted.

  直接可访问的8-取代四氢喹啉在钪(III)三氟甲磺酸催化下发生1,5-氢移位引发的环化反应，以产生难以获得的苯并喹啉衍生物，收率为21-98%。此外，突出了该反应的范围、几种后续转化以及在优化条件过程中发现的一个显著的副反应过程。

• Investigations concerning the organolanthanide and group 3 metallocene-catalyzed cyclization–functionalization of nitrogen-containing dienes
  作者：Gary A. Molander、Jan Antoinette C. Romero

  DOI：10.1016/j.tet.2005.01.048

  日期：2005.3

  Organolanthanide catalyzed cyclization-silylation of nitrogen-containing polyunsaturated systems allows access to core structures commonly found in naturally occurring alkaloids. Nitrogen-containing dienes with various substitution patterns were investigated. The method was most successful for substrates with terminal alkenes. Cyclization upon pendant 1,1-disubstituted olefins was not realized under various conditions. Interestingly, sterically hindered sulfonamides, which were previously believed to render the catalyst inactive, were actually compatible with the catalyst, thus affording the cyclized products after prolonged reaction times. Variations using fused ring systems were also investigated. (C) 2005 Elsevier Ltd. All rights reserved.