N-tosyl-7-methoxy-1,2-dihydroquinoline | 168648-70-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-tosyl-7-methoxy-1,2-dihydroquinoline
• 英文别名: 7-methoxy-1-(4-methylphenyl)sulfonyl-2H-quinoline
• CAS: 168648-70-2
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: QZLYKOPUEXGAGK-UHFFFAOYSA-N

物化性质

• 沸点：
  487.1±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：

  甲氧苯醌 、 N-tosyl-7-methoxy-1,2-dihydroquinoline 在 titanium(IV) isopropylate 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到N-tosyl-3,9-dimethoxy-8-hydroxy-5-azapterocarpan
  参考文献：
  名称：

  1,4-苯醌单-和双酰亚胺与苯乙烯基体系的环加成反应：氮取代的氮杂ero果，蝶果，2-芳基-2,3-二氢吲哚和-二氢苯并呋喃的新合成

  摘要：

  1，4-苯醌，1，4-苯醌双和单酰亚胺与各种2 H-色烯，N-甲苯磺酰基-1,2-二氢喹啉和苯乙烯的路易斯酸促进反应，区域和立体选择性地产生标题化合物，收率高。

  DOI：

  10.1016/0040-4039(95)00375-m
• 作为产物：
  描述：

  2-溴-5-甲氧基苯胺 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 吡啶 、 potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 37.5h， 生成 N-tosyl-7-methoxy-1,2-dihydroquinoline
  参考文献：
  名称：

  N-杂环碳氢化物与氢化钌异构化和环异构化的发展及其在杂环合成中的应用

  摘要：

  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。

  DOI：

  10.1021/jo060308u

文献信息

• Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis
  作者：Yunfei Zhang、Jae Hun Sim、Samantha N. MacMillan、Tristan H. Lambert

  DOI：10.1021/acs.orglett.0c02116

  日期：2020.8.7

  The synthesis of 1,2-dihydroquinolines by the hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) of N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnish quinoline. In comparison with related oxygen-containing substrates, the

  报道了通过N-异戊二烯基化 2-氨基苯甲醛的肼催化闭环羰基-烯烃复分解 (RCCOM) 合成 1,2-二氢喹啉。显示了具有多种替代模式的基材。氮原子上带有酸不稳定的保护基团，原位脱保护和自动氧化得到喹啉。与相关的含氧底物相比，催化循环的环加成步骤较慢，但发现环化更容易。
• Switchable regioselectivity in lewis acid-promoted reactions of 1,4-benzoquinone monoimides with styrenyl systems: Selective syntheses of either 2-aryl-2,3-dihydrobenzofurans or 2-aryl-2,3-dihydroindoles
  作者：Thomas A. Engler、Wenying Chai、Kenneth O. Lynch

  DOI：10.1016/0040-4039(95)01449-r

  日期：1995.9

  Reactions of 4-(N-phenylsulfonyl)-2-alkoxy-1,4-benzoquinone monoimines with electron-rich propenylbenzenes promoted by BF3 yield 7-alkoxy-2-aryl-3-methyl-5-(N-phenylsulfonyl)amino-2,3-dihydrobenzofurans nearly exclusively; whereas, promotion of the reactions by >2 equiv of Ti(IV) gives mainly N-phenylsulfonyl-6alkoxy-2-aryl-5-hydroxy-3-methyl-2,3-dihydoinidoles.
• Lewis Acid-Controlled Regioselectivity in Reactions of Styrenyl Systems with Benzoquinone Monoimides:  New Regioselective Syntheses of Substituted 2-Aryl-2,3-dihydrobenzofurans, 2-Aryl-2,3-dihydroindoles, and 2-Arylindoles
  作者：Thomas A. Engler、Wenying Chai、Kenneth O. LaTessa

  DOI：10.1021/jo9617068

  日期：1996.1.1

  Reactions of 4-(N-phenylsulfonyl)-2-alkoxy-1,4-benzoquinone monoimines 2-4 with electron-rich propenylbenzenes promoted by BF3 yield 7-alkoxy-2-aryl-3-methyl-5-[(N-phenylsulfonyl)amino]2,3-dihydrobenzofurans 5-7 nearly exclusively, whereas promotion of the reactions by Ti4+ gives mixtures of the dihydrobenzofurans and their N-(phenylsulfonyl)-6-alkoxy-2-aryl-5-hydroxy-3-methyl-2,3-dihydroindole isomers 8-10, depending upon substituents present on the propenylbenzene. However, reactions promoted with excess Ti4+, as mixtures of TiCl4:Ti(OiPr)(4), give the dihydroindoles as nearly the exclusive products. Evidence for a mechanism involving initial 5 + 2 cycloaddition of the Lewis acid-bound quinone monoimide with the propenylbenzene is found in reactions of styrenes 1f/g with monoimide 3 in which 7-aryl-3-hydroxy-6-methylbicyclo[3.2.1]oct-3-ene-2,8-diones 33 (5 + 2 adducts) are isolated. These reactions have been applied to stereoselective syntheses of pterocarpans bearing N-phenylsulfonyl groups, azapterocarpans and diazapterocarpans. In addition, DDQ oxidation of derivatives of several of the 2-aryl-2,3-dihydroindoles afford the corresponding 2-arylindoles in good yield. Finally, the experimental details of a general synthetic approach to 7-alkoxy-benzofuranoid neolignans, including (+/-)-licarin B and eupomatenoids-1 and -12 are reported.
• Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues
  作者：Thomas A. Engler、Kenneth O. LaTessa、Rajesh Iyengar、Wenying Chai、Konstantinos Agrios

  DOI：10.1016/0968-0896(96)00192-7

  日期：1996.10

  Oxygenated pterocarpans and 5-azapterocarpans are prepared utilizing Lewis acid-promoted reactions of 2-alkoxy-1,4-benzoquinones with 2H-chromenes and N-tosyl-3,2-dihydroquinolines, respectively. Similarly, benzannulated analogues are prepared via reactions of 5-alkoxy-1,4-naphthoquinones with chromenes, and related 2-aryl-2,3-dihydrobenzofurans result from reactions of styrenes with the quinones. Syntheses of 5-thiapterocarpans are also described utilizing Pd(0)-coupling of o-chloromercuriophenols with 2H-chromenes. Copyright (C) 1996 Elsevier Science Ltd
• Tokuyama, Hidetoshi; Sato, Masashi; Ueda, Toshihiro, Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
  作者：Tokuyama, Hidetoshi、Sato, Masashi、Ueda, Toshihiro、Fukuyama, Tohru

  DOI：——

  日期：——