10,11-dihydro-10,10-dimethyl-7-phenyl-7H-chromeno[4,3-b]quinoline-6,8(9H,12H)-dione | 1372100-48-5

• 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: 10,11-dihydro-10,10-dimethyl-7-phenyl-7H-chromeno[4,3-b]quinoline-6,8(9H,12H)-dione
• 英文别名: 10,10-dimethyl-7-phenyl-7,10,11,12-tetrahydro-6H-chromeno[4,3-b]quinoline-6,8(9H)-dione；10,10-dimethyl-7-phenyl-7,10,11,12-tetrahydro-9H-chromeno[4,3-b]quinoline-6,8-dione；10,11-Dihydro-10,10-dimethyl-7-phenyl-7h-chromeno[4,3-b]quinoline-6,8(9h,12h)-dione；10,10-dimethyl-7-phenyl-7,9,11,12-tetrahydrochromeno[4,3-b]quinoline-6,8-dione
• CAS: 1372100-48-5
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: LGLSODQBDLKONL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 10,11-dihydro-10,10-dimethyl-7-phenyl-7H-chromeno[4,3-b]quinoline-6,8(9H,12H)-dione
  参考文献：
  名称：

  An Efficient One-Pot Three-Component Synthesis of Highly Functionalized Coumarin Fused Indenodihydropyridine and Chromeno[4,3-b]quinoline Derivatives

  摘要：

  An efficient one-pot, three-component synthesis method of highly functionalized coumarin fused 7,13-dihydro-5-oxa-13-aza-indeno[2,1-b]phenanthrene and chromeno[4,3-b]quinoline derivatives was accomplished using aromatic aldehyde, 4-aminocoumarin and cyclic 1,3-dione in acetic acid at reflux temperature. Environmental-friendly protocol has advantages of high yields, creating three new bonds and one stereocenter in single operation. Further, XRD and DFT study confirmed the molecular structure, stability and different interaction in the crystal packing.

  DOI：

  10.3987/com-12-12494

文献信息

• Green synthetic approach toward new chromeno[4,3-b]quinoline and chromeno[4,3-b]pyridine derivatives
  作者：Abolfazl Olyaei、Reyhaneh Mohammad Ebrahimi、Alireza Adl、Mahdieh Sadeghpour

  DOI：10.1007/s10593-019-02585-4

  日期：2019.11

  A facile, convenient, and efficient synthesis of new chromeno[4,3-b]quinoline and chromeno[4,3-b]pyridine derivatives has been accomplished via one-pot three-component reaction of 4-aminocoumarin, 1,3-dicarbonyl compounds (dimedone and Meldrum's acid), and substituted aromatic aldehydes in H2O or EtOH under reflux conditions using 10 mol % of guanidine hydrochloride as organocatalyst. Formation of

  通过4-氨基香豆素、1,3-的一锅三组分反应，实现了一种简便、高效的新型色烯[4,3-b]喹啉和色烯[4,3-b]吡啶衍生物的合成。使用 10 mol% 的盐酸胍作为有机催化剂，在回流条件下，在 H2O 或 EtOH 中的二羰基化合物（二甲酮和 Meldrum 酸）和取代的芳香醛。产物的形成通过串联的 Knoevenagel 和 Michael 反应进行，然后是伴随的环化和脱水或脱羧。所开发的协议可以容忍多种芳香醛。这种环境友好的合成方法的优点是反应时间短、原子经济性高、操作简单、应用容易获得的催化剂、产品收率高、后处理程序简单、
• Novel marine‐based gold nanocatalyst in solvent‐free synthesis of polyhydroquinoline derivatives: Green and sustainable protocol
  作者：Mahsa Sepahvand、Foad Buazar、Mohammad Hosein Sayahi

  DOI：10.1002/aoc.6000

  日期：2020.12

  11 ± 1.5 nm in transmission electron microscopy (TEM) and exhibited a crystal structure of face‐centered cubic in X‐ray diffraction (XRD) analyses. Our results indicated that bioinspired AuNPs demonstrate superior catalytic activity in the safe and facile one‐pot synthesis of polyhydroquinoline derivatives under solvent‐free reaction conditions. This green route encompasses multiple benefits including

  我们报告了一种环保的合成方法，该方法利用富电子海参提取物作为生物还原剂和稳定剂，在最佳条件下将金阳离子还原为AuNPs，从而制备生物金纳米颗粒（AuNPs）。所产生的AuNP呈球形，在透射电子显微镜（TEM）中的平均粒径为11±1.5 nm，并且在X射线衍射（XRD）分析中显示出面心立方的晶体结构。我们的结果表明，在无溶剂的反应条件下，以生物为灵感的AuNPs在安全，便捷的一锅法合成多氢喹啉衍生物中显示出优异的催化活性。这条绿色路线包含多项优势，包括可高度循环利用的生物启发催化剂（5个循环），较短的反应时间，方便的锻炼，
• An efficient four-component reaction for the synthesis of chromeno[4,3-b]quinolone derivatives
  作者：Azadeh Yahya-Meymandi、Hamideh Nikookar、Setareh Moghimi、Mohammad Mahdavi、Loghman Firoozpour、Ali Asadipour、Parviz Rashidi Ranjbar、Alireza Foroumadi

  DOI：10.1007/s13738-016-1027-3

  日期：2017.4

  Chromenoquinolines have been prepared via an efficient one-pot, multi-component reaction of 4-hydroxy coumarin, aqueous ammonia, dimedone and different aldehydes.

  铬喹啉是通过4-羟基香豆素，氨水，二甲酮和不同醛的高效一锅多组分反应制得的。
• An efficient green protocol for the synthesis of coumarin fused highly decorated indenodihydropyridyl and dihydropyridyl derivatives
  作者：Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.02.077

  日期：2012.4

  A simple, convenient, environmentally benign, and mild synthetic method has been established to afford highly decorated indenodihydropyridine and dihydropyridine derivatives employing a green solvent ethyl-L-lactate and an organo-catalyst (+/-)lactic acid. A wide range of functional groups were tolerated in the developed protocol. The target molecules were obtained in moderate to good yields applying the current method. (c) 2012 Elsevier Ltd. All rights reserved.
• An Efficient One-Pot Three-Component Synthesis of Highly Functionalized Coumarin Fused Indenodihydropyridine and Chromeno[4,3-b]quinoline Derivatives
  作者：Naseem Ahmed、B. Venkata Babu、Sandeep Singh、Petar M. Mitrasinovic

  DOI：10.3987/com-12-12494

  日期：——

  An efficient one-pot, three-component synthesis method of highly functionalized coumarin fused 7,13-dihydro-5-oxa-13-aza-indeno[2,1-b]phenanthrene and chromeno[4,3-b]quinoline derivatives was accomplished using aromatic aldehyde, 4-aminocoumarin and cyclic 1,3-dione in acetic acid at reflux temperature. Environmental-friendly protocol has advantages of high yields, creating three new bonds and one stereocenter in single operation. Further, XRD and DFT study confirmed the molecular structure, stability and different interaction in the crystal packing.