3-(1-hydroxybut-3-enyl)-8-methyl-1H-quinolin-2-one | 950834-75-0

• 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: 3-(1-hydroxybut-3-enyl)-8-methyl-1H-quinolin-2-one
• CAS: 950834-75-0
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: JJRLQLQUHSPGFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-hydroxybut-3-enyl)-8-methyl-1H-quinolin-2-one 在 碘 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 15.5h， 生成
  参考文献：
  名称：

  Synthesis of diastereomeric 2,4-disubstituted pyrano[2,3-b]quinolines from 3-formyl-2-quinolones through O–C bond formation via intramolecular electrophilic cyclization

  摘要：

  A number of 3-homoallyl-2-quinolones have been synthesized from 3-formyl-2-quinolones by reaction with allylindium bromide in aqueous DMF. Intramolecular electrophilic cyclization of these quinolones with iodine afforded either exclusively, or predominantly, racemic cis-diastereoisomers. Nucleophilic substitution reactions at the iodomethyl group afforded a mixture of tetracyclic products and unreacted racernic trans-diastereoisomer. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.127
• 作为产物：
  描述：

  2-氯-8-甲基喹啉-3-甲醛 在 indium 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(1-hydroxybut-3-enyl)-8-methyl-1H-quinolin-2-one
  参考文献：
  名称：

  Synthesis of diastereomeric 2,4-disubstituted pyrano[2,3-b]quinolines from 3-formyl-2-quinolones through O–C bond formation via intramolecular electrophilic cyclization

  摘要：

  A number of 3-homoallyl-2-quinolones have been synthesized from 3-formyl-2-quinolones by reaction with allylindium bromide in aqueous DMF. Intramolecular electrophilic cyclization of these quinolones with iodine afforded either exclusively, or predominantly, racemic cis-diastereoisomers. Nucleophilic substitution reactions at the iodomethyl group afforded a mixture of tetracyclic products and unreacted racernic trans-diastereoisomer. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.127

文献信息

• Electrophile-induced domino cyclization reaction for the synthesis of 2,2a,10,11-tetrahydrofuro[2′,4′:4,6]pyrano[2,3-b]quinolines
  作者：Bhawana Singh、Atish Chandra、Shraddha Upadhyay、Radhey M. Singh、M.C. Puerta、Pedro Valerga

  DOI：10.1016/j.tetlet.2008.08.079

  日期：2008.11

  A new and efficient synthesis of furo[2',4':4,6]pyrano[2,3-b]quinolines, via a domino cyclization approach, has been achieved by iodine and mercuric oxide-catalyzed intramolecular cyclization of 3-homoallyl-2-quinolones in acetic acid. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of diastereomeric 2,4-disubstituted pyrano[2,3-b]quinolines from 3-formyl-2-quinolones through O–C bond formation via intramolecular electrophilic cyclization
  作者：Mrityunjay K. Singh、Atish Chandra、Bhawana Singh、Radhey M. Singh

  DOI：10.1016/j.tetlet.2007.06.127

  日期：2007.8

  A number of 3-homoallyl-2-quinolones have been synthesized from 3-formyl-2-quinolones by reaction with allylindium bromide in aqueous DMF. Intramolecular electrophilic cyclization of these quinolones with iodine afforded either exclusively, or predominantly, racemic cis-diastereoisomers. Nucleophilic substitution reactions at the iodomethyl group afforded a mixture of tetracyclic products and unreacted racernic trans-diastereoisomer. (c) 2007 Elsevier Ltd. All rights reserved.