5-Bromo-6-(ethylamino)chromen-2-one | 1023659-37-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-Bromo-6-(ethylamino)chromen-2-one
• CAS: 1023659-37-1
• 化学式: C₁₁H₁₀BrNO₂
• 分子量: 268.11
• InChiKey: FOIZRHIGYICOGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Bromo-6-(ethylamino)chromen-2-one 在 iron(III) chloride 、 sodiumsulfide nonahydrate 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-ethylchromeno[5,6-b][1,4]thiazine-3,8(2H,4H)-dione
  参考文献：
  名称：

  有效的无配体氯化铁催化合成的1,4-噻嗪-3-one衍生物

  摘要：

  通过在无配体条件下使用硫化钠作为硫源和氯化铁作为催化剂，已经获得了合成香豆素-，喹诺酮-环化的1,4-噻嗪-3-one衍生物的简便方法。合成过程简单，廉价，并以高收率提供产物。该方法学也适用于萘和苯体系。

  DOI：

  10.1016/j.tetlet.2014.04.005
• 作为产物：
  描述：

  6-ethylamino-coumarin 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 5-Bromo-6-(ethylamino)chromen-2-one
  参考文献：
  名称：

  铁/钯催化的分子内加氢胺化：吡咯修饰的香豆素和喹诺酮衍生物的简便合成

  摘要：

  报道了使用PdCl 2 / FeCl 3催化体系催化的取代胺和游离胺对以杂环为中心的氨基炔烃进行的高效分子内加氢胺化反应，以形成生物学上重要的吡咯香豆素和吡咯并喹诺酮衍生物。在该策略中同时使用具有不同杂环骨架的脂族和芳族取代炔烃证明了该方法的多样性。 加氢胺化-吡咯并香豆素-吡咯并喹诺酮-FeCl 3-氨基炔

  DOI：

  10.1055/s-0030-1258311

文献信息

• Regioselective synthesis of pyrano[3,2-f]quinoline and phenanthroline derivatives using molecular iodine
  作者：K.C. Majumdar、Sudipta Ponra、Tapas Ghosh

  DOI：10.1016/j.tetlet.2013.07.163

  日期：2013.10

  A series of polysubstituted pyrano[3,2-f]quinoline and phenanthroline derivatives have been synthesized by molecular iodine-catalyzed tandem reaction of various propargylic alcohols with or without substituted amines in excellent yields. Moreover, the cyclized side products are also pyrano[3,2-f]quinoline and phenanthroline derivatives.

  已经通过分子碘催化具有或不具有取代胺的各种炔丙醇的串联催化合成了一系列多取代的吡喃并[3,2- f ]喹啉和菲咯啉衍生物。此外，环化副产物也是吡喃并[3，2- f ]喹啉和菲咯啉衍生物。
• A Short Route to the Synthesis of Pyrrolocoumarin and Pyrroloquinolone Derivatives by Sonogashira Cross-Coupling and Gold-Catalyzed Cycloisomerization of Acetylenic Amines
  作者：Krishna Majumdar、Buddhadeb Chattopadhyay、Srikanta Samanta

  DOI：10.1055/s-0028-1083295

  日期：2009.1

  The syntheses of pyrrolocoumarin and pyrroloquinolone derivatives have been achieved in excellent yields from the acetylenic amines by gold-catalyzed cycloisomerization in the absence of any silver salts or any other bases. The acetylenic amines were in turn obtained by Sonogashira coupling of the corresponding coumarin and quinolone derivatives. coumarin - quinolone - Sonogashira coupling - gold catalysis

  在没有任何银盐或任何其他碱的情况下，通过金催化的环异构化反应，由乙炔胺以优异的产率获得了吡咯香豆素和吡咯并喹诺酮衍生物的合成。炔胺又通过Sonogashira偶联相应的香豆素和喹诺酮衍生物而获得。 香豆素-喹诺酮-Sonogashira偶联-金催化-分子内环化-环异构化
• Catalyst-Free 1,3-Dipolar Cycloaddition: An Efficient Route for the Formation of the 1,2,3-Triazole-Fused Diazepinone Framework
  作者：K. Majumdar、Krishanu Ray、Sintu Ganai、Tapas Ghosh

  DOI：10.1055/s-0029-1218610

  日期：2010.3

  A catalyst-free, effective method for the synthesis of the hitherto unreported 1,2,3-triazole-fused diazepinone framework in good to excellent yield through 1,3-dipolar cycloaddition is reported. The generality of the reaction is demonstrated by the synthesis of an array of [1,2,3]triazolodiazepinones. The methodology offers a clean reaction and easy isolation of the products in good to excellent yield.
• Synthesis of novel pyrano[3,2-f]quinoline, phenanthroline derivatives and studies of their interactions with proteins: An application in mammalian cell imaging
  作者：K.C. Majumdar、Sudipta Ponra、Tapas Ghosh、Ratan Sadhukhan、Utpal Ghosh

  DOI：10.1016/j.ejmech.2013.10.067

  日期：2014.1

  A series of tri-cyclic pyrano[3,2-f]quinoline and phenanthroline derivatives have been synthesized by a HCl-mediated 6-'endo-trig' Michael type ring closure reaction of 6-amino-5-(3-hydroxy-3-methylbut-1-ynyl)-2H-chromen-2-one in excellent yields. The process is very simple, facile and inexpensive and can provide a diverse range of substituted quinoline derivatives from simple and easily available starting materials. Moreover, the synthesized derivatives exhibit staining property to the cultured HeLa cells after fixing and can be used as fluorophores which can bind with protein molecule. (C) 2013 Published by Elsevier Masson SAS.
• Palladium-Mediated Reductive Heck Cyclization for the Formation of Dibenzoazepinone Framework
  作者：K. Majumdar、Santanu Chakravorty、Tapas Ghosh、B. Sridhar

  DOI：10.1055/s-0029-1218298

  日期：2009.12

  The dibenzoazepinone framework has been synthesized through a palladium-mediated Sonogashira cross-coupling followed by a reductive Fleck cyclization. The reactions are simple. straightforward, and have been carried Out Under ligand-free conditions.