1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)-3-phenylprop-2-yn-1-one | 1424284-35-4

• 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-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)-3-phenylprop-2-yn-1-one
• 英文别名: 1-(6-methoxy-3,4-dihydro-2H-quinolin-1-yl)-3-phenylprop-2-yn-1-one
• CAS: 1424284-35-4
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: NLLCWVZUGCQXMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)-3-phenylprop-2-yn-1-one 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以91%的产率得到2-iodo-1-phenyl-6,7-dihydro-3H-pyrrolo[2,1-j]quinoline-3,9(5H)-dione
  参考文献：
  名称：

  Synthesis of pyrrolo-[2,1-j]quinolone framework via intramolecular electrophilic ipso-cyclization

  摘要：

  The challenging pyrrolo-12,1-j]quinolone core structure has been synthesized from N-(alkynoyl)-6-methoxytetrahydroquinoline in good yields using electrophilic cyclization as the key step. These reactions require simple starting materials and mild reaction conditions. In addition, we have demonstrated that the iodine moiety, which could be easily introduced in the final step, is very useful for further functionalization by employing various palladium-catalyzed cross-coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.014
• 作为产物：
  描述：

  6-甲氧基-1,2,3,4-四氢喹啉 、 苯丙炔酸 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以80%的产率得到1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)-3-phenylprop-2-yn-1-one
  参考文献：
  名称：

  Synthesis of pyrrolo-[2,1-j]quinolone framework via intramolecular electrophilic ipso-cyclization

  摘要：

  The challenging pyrrolo-12,1-j]quinolone core structure has been synthesized from N-(alkynoyl)-6-methoxytetrahydroquinoline in good yields using electrophilic cyclization as the key step. These reactions require simple starting materials and mild reaction conditions. In addition, we have demonstrated that the iodine moiety, which could be easily introduced in the final step, is very useful for further functionalization by employing various palladium-catalyzed cross-coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.014

文献信息

• Ag-Catalyzed Oxidative <i>ipso</i>-Cyclization via Decarboxylative Acylation/Alkylation: Access to 3-Acyl/Alkyl-spiro[4.5]trienones
  作者：Chada Raji Reddy、Dattahari H. Kolgave、Muppidi Subbarao、Mounika Aila、Santosh Kumar Prajapti

  DOI：10.1021/acs.orglett.0c01588

  日期：2020.7.17

  A strategy to functionalized spiro[4.5]trienones, by domino silver-catalyzed decarboxylative acylation or alkylation/ ipso-cyclization of N-arylpropiolamides with α-keto acids/alkyl carboxylic acids, is presented. This transformation offers a wide range of substituted 3-acyl/alkyl-spiro[4.5]trienones in high yields with a broad substrate scope. The approach was further extended to access fused tricyclic

  的策略官能螺[4.5] trienones，通过多米诺银催化的脱羧酰化或烷基化/烷基本位的-cyclization Ñ与-arylpropiolamidesα酮酸/烷基羧酸，被呈现。该转化以高收率和广泛的底物范围提供了广泛的取代的3-酰基/烷基-螺[4.5]三烯酮。该方法进一步延长到接入稠合三环框架，6,7-二氢-3- ħ吡咯并[2,1- Ĵ ]喹啉-3,9-（5 ħ） -二酮。
• Na ₂ S ₂ O ₈ ‐Promoted Radical Cyclization for the Synthesis of Azaspiro[4.5]deca‐3,6,9‐triene‐2,8‐dione and Pyrrolo[2,1‐ <i>j</i> ]quinolone Derivatives
  作者：C. Ravikumar Reddy、Suresh Yarlagadda、Boora Ramesh、M. Rajashekhar Reddy、B. Sridhar、B. V. Subba Reddy

  DOI：10.1002/ejoc.201700058

  日期：2017.4.26

  An efficient radical cyclization of N‐(4‐methoxyphenyl)‐N‐methyl‐3‐phenylpropiolamides with 1‐phenylcyclopropan‐1‐ols has been achieved using Na2S2O8 to produce azaspiro[4.5]deca‐3,6,9‐triene‐2,8‐diones. Similarly, the reaction of 1‐[6‐methoxy‐3,4‐dihydroquinolin‐1(2H)‐yl]‐3‐phenylprop‐2‐yn‐1‐ones with 1‐phenylcyclopropan‐1‐ols gives 6,7‐dihydro‐3H‐pyrrolo[2,1‐j]quinoline‐3,9(5H)‐diones.

  使用Na 2 S 2 O 8生成氮杂螺[4.5] deca-3,6，可以有效地将N-（4-甲氧基苯基）-N-甲基-3-苯基丙酰胺与1-苯基环丙烷-1-醇进行自由基环化。9-三烯-2,8-二酮。同样，1- [6-甲氧基-3,4-二氢喹啉-1（2 H）-基] -3-苯基丙-2-炔-1-酮与1-苯基环丙-1-醇的反应得到6,7二氢-3- ħ吡咯并[2,1- Ĵ ]喹啉-3,9-（5 ħ） -二酮。
• Expeditious Access to Spiro-Fused 2,5-Cyclohexadienones <i>via</i> Thio(seleno)cyanative <i>ipso</i>-Cyclization
  作者：Chada Raji Reddy、Uprety Ajaykumar、Dattahari H. Kolgave

  DOI：10.1021/acs.joc.0c02270

  日期：2020.12.4

  A facile oxidative dearomatization of N-(p-methoxyaryl)propiolamides has been established for the synthesis of spiro-fused 2,5-cyclohexadienone frameworks via thio(seleno)cyanative ipso-cyclization in the presence of ceric ammonium nitrate (CAN) as the oxidant. The present method, involving the formation of C–S and C–C bonds, was also extended to (p-methoxyaryl)propiolates for thiocyanative ipso-cyclization

  的一种简便的氧化脱芳构化ñ - （p -methoxyaryl）propiolamides已建立螺稠合的2,5-环己二烯酮框架的合成通过硫代（硒）cyanative本位-cyclization在硝酸铈铵（CAN）作为存在氧化剂。本发明的方法，涉及C-S和C-C键的形成，也扩展到（p -methoxyaryl）的丙炔酸酯为thiocyanative本位-cyclization。此外，将获得的硫属元素基-螺环己二酮转化为独特官能化的螺环己二酮衍生物。
• Copper(<scp>ii</scp>)-catalyzed oxidative <i>ipso</i>-annulation of <i>N</i>-arylpropiolamides and biaryl ynones with 1,3-diketones: construction of diketoalkyl spiro-trienones
  作者：Chada Raji Reddy、Dattahari H. Kolgave、Uprety Ajaykumar、Remya Ramesh

  DOI：10.1039/d2ob01282k

  日期：——

  A diverse range of diketoalkylated spiro-trienones involving a copper(ii)-catalyzed cascade radical addition/ipso-annulation/dearomatization reaction of N-arylpropiolamides and biaryl ynones are synthesized.

  合成了一系列不同的二酮基螺环三烯酮，该反应涉及铜（II）催化的级联自由基加成/ ipso-环化/去芳香化反应，使用N-芳基丙炔酰胺和双芳基炔酮。
• Synthesis of pyrrolo-[2,1-j]quinolone framework via intramolecular electrophilic ipso-cyclization
  作者：Lila Low-Beinart、Xiaohan Sun、Eli Sidman、Tanay Kesharwani

  DOI：10.1016/j.tetlet.2012.12.014

  日期：2013.3

  The challenging pyrrolo-12,1-j]quinolone core structure has been synthesized from N-(alkynoyl)-6-methoxytetrahydroquinoline in good yields using electrophilic cyclization as the key step. These reactions require simple starting materials and mild reaction conditions. In addition, we have demonstrated that the iodine moiety, which could be easily introduced in the final step, is very useful for further functionalization by employing various palladium-catalyzed cross-coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.