2-oxo-2H-benzo[g]chromene-3-carboxylic acid | 82119-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-oxo-2H-benzo[g]chromene-3-carboxylic acid
• 英文别名: 2H-benzo[g]chromen-2-one-3-carboxylic acid；2-Oxo-2H-benzo[g]chromen-3-carbonsaeure；2-oxobenzo[g]chromene-3-carboxylic acid
• CAS: 82119-81-1
• 化学式: C₁₄H₈O₄
• 分子量: 240.215
• InChiKey: MKUZSPRQSHPWCE-UHFFFAOYSA-N

物化性质

• 沸点：
  486.2±33.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-oxo-2H-benzo[g]chromene-3-carboxylic acid 在 溶剂黄146 、 silver carbonate 作用下， 以 2,4-滴二甲胺盐 为溶剂， 反应 16.0h， 以67%的产率得到8-(naphthalen-1-yl)-2H-chromen-2-one
  参考文献：
  名称：

  银催化香豆素-3-羧酸的轻松脱羧

  摘要：

  已经开发了具有温和反应条件的简单且高效的方案，该方案允许各种功能化的香豆素-3-羧酸的平滑的丙级羧化。在催化量的Ag 2 CO 3和乙酸的存在下，即使未活化的香豆素-3-羧酸也以良好的产率转化为优异的产率，并且易于制备成相应的香豆素衍生物。

  DOI：

  10.1016/j.tet.2010.10.019
• 作为产物：
  描述：

  3-乙酰基氧基-2-萘甲酸 在 Pd-BaSO₄ 、 氯化亚砜 、 乙醇 、 苯胺 、 xylene 作用下， 生成 2-oxo-2H-benzo[g]chromene-3-carboxylic acid
  参考文献：
  名称：

  Zur Kenntnis des dritten ortho-Oxynaphthaldehyds und der isomeren ß-Naphthocumarine

  摘要：

  DOI：

  10.1002/ardp.19312690105

文献信息

• Improvement of Fluorescence Characteristics of Coumarins: Syntheses and Fluorescence Properties of 6-Methoxycoumarin and Benzocoumarin Derivatives as Novel Fluorophores Emitting in the Longer Wavelength Region and Their Application to Analytical Reagents
  作者：Chiyomi Murata、Toshinobu Masuda、Yasuko Kamochi、Kenichiro Todoroki、Hideyuki Yoshida、Hitoshi Nohta、Masatoshi Yamaguchi、Akira Takadate

  DOI：10.1248/cpb.53.750

  日期：——

  To improve the fluorescence characteristics, especially emission wavelength, of coumarins, various 3-substituted-6-methoxycoumarin derivatives were synthesized, and then benzocoumarin derivatives were also synthesized in expectation of the shift to the longer wavelength region by the extension of the conjugated system. Their fluorescence properties were investigated spectrophotometrically in acetonitrile and evaluated from the viewpoint of the intramolecular charge transfer (ICT) between push- and pull-substituents in the ground and the excited states. Among them, benzocoumarin derivatives especially fluoresced in the longer wavelength around 540 nm with remarkably large Stokes shifts beyond 10000 cm−1. Using such fluorophores, some novel fluorescence derivatization reagents for carboxylic acids, alcohols, phenols, and amines were preliminarily prepared as an example, and their derivatized products were also found to fluoresce in the longer wavelength region with large Stokes shifts.

  为了改善香豆素的荧光特性，特别是发射波长，合成了多种3取代-6-甲氧基香豆素衍生物，随后又合成了苯香豆素衍生物，期待通过延长共轭体系实现向长波长区域的转移。采用光谱法在乙腈中研究了它们的荧光特性，并从基态和激发态中推送和拉动取代基之间的分子内电荷转移（ICT）角度进行了评估。在这些衍生物中，苯香豆素衍生物特别在540 nm附近的长波长范围内具有显著的荧光，斯托克斯位移超过10000 cm−1。利用这些荧光基团，初步制备了一些新型的荧光衍生化试剂用于羧酸、醇、酚和胺，发现其衍生化产物在长波长区域也具有显著的荧光和较大的斯托克斯位移。
• Synthesis and Characterization of Immobilized Lipase on Fe3O4 Nanoparticles as Nano biocatalyst for the Synthesis of Benzothiazepine and Spirobenzothiazine Chroman Derivatives
  作者：Robabeh Baharfar、Saadieh Mohajer

  DOI：10.1007/s10562-016-1797-3

  日期：2016.9

  A retrievable nanostructure heterogeneous catalyst, based on lipase (lipase from the fungus Aspergillus niger), namely Fe3O4-bonded lipase (Fe3O4 NPs@ lipase) was prepared in nano size and fully characterized by several techniques such as Fourier transform infrared spectroscopy, X-ray diffraction, Scanning electron microscopy, Transmission electron microscopy and Vibrating sample magnetometer. The

  基于脂肪酶（来自真菌黑曲霉的脂肪酶），即 Fe3O4 键合脂肪酶（Fe3O4 NPs@脂肪酶），制备了纳米尺寸的可回收纳米结构多相催化剂，并通过傅里叶变换红外光谱、X 射线等多种技术进行了充分表征。衍射、扫描电子显微镜、透射电子显微镜和振动样品磁强计。通过香豆素-3-羧酸衍生物、2-氨基苯硫酚和烷基异氰化物在室温温和条件下的三组分反应，该可回收纳米结构催化剂被认为是合成苯并噻嗪和螺苯并噻嗪色满衍生物的有效催化剂。 .
• Synthesis of coumarins derivatives via decarboxylative cross-coupling of coumarin-3-carboxylic acid with benzylic C(sp3)-H bond
  作者：Shuang-hong Hao、Li-Xia Li、Dao-Qing Dong、Zu-Li Wang、Xian-Yong Yu

  DOI：10.1016/j.tetlet.2018.10.001

  日期：2018.11

  The reaction of coumarin-3-carboxylic acid with benzylic C(sp3)-H bond was established in this paper. A series of 3-benzylcoumarin derivatives were efficiently isolated in moderated to high yield using Cu(OAc)2 as catalyst and TBPB as oxidant.

  建立了香豆素-3-羧酸与苄基C（sp3）-H键的反应。使用Cu（OAc）2作为催化剂和TBPB作为氧化剂，可以中等至高收率高效分离出一系列3-苄香豆素衍生物。
• Design, Synthesis, and Cholinesterase Inhibition Assay of Coumarin‐3‐carboxamide‐ <i>N</i> ‐morpholine Hybrids as New Anti‐Alzheimer Agents
  作者：Maliheh Barazandeh Tehrani、Zahra Rezaei、Mehdi Asadi、Hossein Behnammanesh、Hamid Nadri、Fatemeh Afsharirad、Alireza Moradi、Bagher Larijani、Maryam Mohammadi‐Khanaposhtani、Mohammad Mahdavi

  DOI：10.1002/cbdv.201900144

  日期：2019.7

  Among them, propylmorpholine derivative 5g (N-[3-(morpholin-4-yl)propyl]-2-oxo-2H-chromene-3-carboxamide) bearing an unsubstituted coumarin moiety and ethylmorpholine derivative 5d (6-bromo-N-[2-(morpholin-4-yl)ethyl]-2-oxo-2H-chromene-3-carboxamide) bearing a 6-bromocoumarin moiety showed the most activity against AChE and BuChE, respectively. The inhibitory activity of compound 5g against AChE was

  设计并合成了一系列新的香豆素-3-羧酰胺-N-吗啉杂化物5a-5l作为胆碱酯酶抑制剂。标题化合物的合成方法始于2-羟基苯甲醛衍生物与Meldrum's酸的反应，得到相应的香豆素3-羧酸。然后，将后面的化合物与2-吗啉代乙胺或N-（3-氨基丙基）吗啉酰胺化导致形成化合物5a-5l。对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）的体外抑制筛选显示，大多数合成的化合物具有有效的AChE抑制作用，而它们的BuChE抑制作用为中度至弱。其中，带有未取代香豆素部分的丙基吗啉衍生物5g（N- [3-（吗啉-4-基）丙基] -2-氧代-2H-色烯-3-羧酰胺）和乙基吗啉衍生物5d（6-溴-N- [2-带有6-溴香豆素部分的（吗啉-4-基）乙基] -2-氧代-2H-亚甲基-3-羧酰胺分别显示出对AChE和BuChE的最大活性。化合物5g对AChE的抑制活性是rivastigmine的1.78倍，化合
• Atom-economical isocyanide-based multicomponent synthesis of 2,5-dioxopyrrolidines, spirobenzothiazinechromans and 1,5-benzothiazepines
  作者：Roya Akbarzadeh、Tayebeh Amanpour、Hamid Reza Khavasi、Ayoob Bazgir

  DOI：10.1016/j.tet.2013.12.011

  日期：2014.1

  An efficient synthesis of new pharmaceutically relevant dioxopyrrolidines, spirobenzo thiazine-2,3'chromans, and benzothiazepines via isocyanide-based multicomponent condensation reactions at room temperature is reported. This synthesis serves as a nice addition to group-assistant-purification (GAP) chemistry in which purification via chromatography and recrystallization can be avoided, and the pure products are obtained simply by washing the crude products with 95% ethanol. (C) 2013 Elsevier Ltd. All rights reserved.