6-甲氧基-1-(4-甲基苯基)磺酰基-2H-喹啉 | 34129-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-甲氧基-1-(4-甲基苯基)磺酰基-2H-喹啉
• 英文名称: N-p-toluenesulfonyl-6-methoxy-1,2-dihydroquinoline
• 英文别名: 6-methoxy-1-(toluene-4-sulfonyl)-1,2-dihydro-quinoline；6-Methoxy-1-(4-methylbenzene-1-sulfonyl)-1,2-dihydroquinoline；6-methoxy-1-(4-methylphenyl)sulfonyl-2H-quinoline
• CAS: 34129-41-4
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: WDEQQHVAYMWZAX-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  496.9±55.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-甲氧基-1-(4-甲基苯基)磺酰基-2H-喹啉 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 生成 6-甲氧基喹啉
  参考文献：
  名称：

  Tokuyama, Hidetoshi; Sato, Masashi; Ueda, Toshihiro, Heterocycles, 2001, vol. 54, # 1, p. 105 - 108

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲氧基-2-硝基苯甲酸 在 palladium on activated charcoal 吡啶 、 盐酸 、 manganese(IV) oxide 、 Grubbs catalyst first generation 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 33.25h， 生成 6-甲氧基-1-(4-甲基苯基)磺酰基-2H-喹啉
  参考文献：
  名称：

  A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): its application to the synthesis of key intermediates for anti-malarial agents

  摘要：

  A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2-dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.084

文献信息

• Development of Isomerization and Cycloisomerization with Use of a Ruthenium Hydride with <i>N</i>-Heterocyclic Carbene and Its Application to the Synthesis of Heterocycles
  作者：Mitsuhiro Arisawa、Yukiyoshi Terada、Kazuyuki Takahashi、Masako Nakagawa、Atsushi Nishida

  DOI：10.1021/jo060308u

  日期：2006.5.1

  ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline

  第二代Grubbs钌催化剂与乙烯基氧基三甲基硅烷的反应可有效生成具有N-杂环卡宾（NHC）配体的纯氢化钌络合物，并具有明确的特征。该氢化钌络合物对末端烯烃的选择性异构化和1,6-二烯的环异构化显示出高催化活性。的这些反应Ñ -allyl- Ò -vinylaniline导致新的合成方法杂环如吲哚和3-亚甲基-2,3- dihydroindoles，这对于生物活性天然产物有用的合成子。这些程序解决了面向多样性的综合中的一个重要问题。
• The Au(I)-Catalyzed Intramolecular Hydroarylation of Terminal Alkynes Under Mild Conditions: Application to the Synthesis of 2<i>H</i>-Chromenes, Coumarins, Benzofurans, and Dihydroquinolines
  作者：Rajeev S. Menon、Alison D. Findlay、Alex C. Bissember、Martin G. Banwell

  DOI：10.1021/jo902032p

  日期：2009.11.20

  Operationally simple Au(I)-catalyzed intramolecular hydroarylation (IMHA) reactions of terminal alkynes that proceed in high yield and under very mild conditions are described. These processes involve low catalyst loadings, mild reaction temperatures, and short reaction times, require no cocatalysts or additives, and allow for the generation of a number of important heterocyclic motifs from readily

  描述了操作简便的Au（I）催化的末端炔烃分子内氢芳基化（IMHA）反应，该反应以高收率和在非常温和的条件下进行。这些过程涉及低催化剂负载，适度的反应温度和短的反应时间，不需要助催化剂或添加剂，并允许从容易获得的起始原料中产生许多重要的杂环基序。
• Selective Isomerization of a Terminal Olefin Catalyzed by a Ruthenium Complex: The Synthesis of Indoles through Ring-Closing Metathesis
  作者：Mitsuhiro Arisawa、Yukiyoshi Terada、Masako Nakagawa、Atsushi Nishida

  DOI：10.1002/anie.200290031

  日期：2002.12.16
• Decarboxylative cyclizations and cycloadditions of palladium-polarized aza-ortho-xylylenes
  作者：Chao Wang、Nirmal Pahadi、Jon A. Tunge

  DOI：10.1016/j.tet.2009.04.071

  日期：2009.6

  Vinyl benzoxazinones undergo decarboxylation in the presence of palladium catalysts to form palladium-polarized aza-ortho-xylylenes, which are versatile reaction intermediates. These palladium-polarized aza-ortho-xylylenes are generated under exceptionally mild conditions and undergo a plethora of different reactions depending on the reaction conditions. Specifically, they undergo dimerization reactions to produce macrocycles, cyclizations to form dihydroquinolines, cycloadditions with electrophilic p-bonds, and nucleophilic attack by amines. Thus, a wide array of structurally unique aniline derivatives can be accessed from these unique intermediates. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of substituted 1,2-dihydroquinolines and quinolines using ene–ene metathesis and ene–enol ether metathesis
  作者：Mitsuhiro Arisawa、Chumpol Theeraladanon、Atsushi Nishida、Masako Nakagawa

  DOI：10.1016/s0040-4039(01)01714-2

  日期：2001.11

  We describe a novel and convenient method for quinoline synthesis using ring-closing olefin metathesis (RCM), ene-ene metathesis, and ene-enol ether metathesis. We also report the first example of enol silyl ether-ene metathesis to produce cyclic enol silyl ether. Using this method, versatile substituted quinoline derivatives were readily prepared in excellent yield from anthranilic acid derivatives. C 2001 Elsevier Science Ltd. All rights reserved.