MICROWAVE-ASSISTED SYNTHESIS AND PKA DETERMINATION OF UMBELLIFERONE: AN EXPERIMENT FOR THE UNDERGRADUATE ORGANIC CHEMISTRY LABORATORY

被引：2

作者：

Pereira, Thiago M. ^{[1
]}

Franco, Daiana F. P. ^{[1
]}

Vitorio, Felipe ^{[1
]}

Amaral, Ronaldo C. ^{[2
]}

Ponzoni, Aparecida C. ^{[1
]}

Kummerle, Arthur E. ^{[1
]}

机构：

[1] Univ Fed Rural Rio de Janeiro, Dept Quim, BR-23897000 Rio De Janeiro, RJ, Brazil

[2] Inst Fed Educ Ciencia & Tecnol Sao Paulo, Campus Sorocaba, BR-18095410 Sorocaba, SP, Brazil

来源：

QUIMICA NOVA | 2018年 / 41卷 / 10期

关键词：

umbelliferone; microwave; synthesis; undergraduate; pKa; DESIGN;

D O I：

10.21577/0100-4042.20170262

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A synthetic procedure for obtaining the fluorescent coumarin umbelliferone (7-hydroxycoumarin) and its spectral parameters were fully developed aiming at an undergraduate organic chemistry laboratory class. Umbelliferone is traditionally prepared via Pechmann condensation using malic acid, resorcinol and sulfuric acid as catalyst. The use of domestic microwave oven and the absence of solvent allow our methodology to be simple, fast and easy applied in obtaining umbelliferone at organic chemistry laboratory being greener than classical techniques of synthesis. In this class the student will learn how to measure the potency of a microwave oven, the applicability of this kind of irradiation in the organic synthesis of fluorescent compounds and how to determine the pKa of an organic compound through an UV/VIS spectrometric analysis. These experiments were designed to be suitable for a second and third year undergraduate curriculum.

引用

页码：1205 / 1208

页数：4

共 21 条

[1]

Andrade P, 2015, BIOORGAN MED CHEM, V23, P6815, DOI [10.1016/j.bmc.2015.10.008, DOI 10.1016/J.BMC.2015.10.008]

[2] A study of the relationship between the chemical structures and the fluorescence quantum yields of coumarins, quinoxalinones and benzoxazinones for the development of sensitive fluorescent derivatization reagents [J].

Azuma, K ;

Suzuki, S ;

Uchiyama, S ;

Kajiro, T ;

Santa, T ;

Imai, K .

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2003, 2 (04) :443-449

[3] Heating in microwave ovens/developing of basic concepts [J].

Barboza, ACRN ;

Cruz, CVMS ;

Graziani, MB ;

Lorenzetti, MCF ;

Sabadini, E .

QUIMICA NOVA, 2001, 24 (06) :901-904

[4] Improved synthesis of some hydroxycoumarins [J].

Bulut, M ;

Erk, C .

DYES AND PIGMENTS, 1996, 30 (02) :99-104

[5] Microwave-mediated synthesis of lophine: Developing a mechanism to explain a product [J].

Crouch, R. David ;

Howard, Jessica L. ;

Zile, Jennifer L. ;

Barker, Kathryn H. .

JOURNAL OF CHEMICAL EDUCATION, 2006, 83 (11) :1658-1660

[6] Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore [J].

Du, Lupei ;

Li, Minyong ;

Zheng, Shilong ;

Wang, Binghe .

TETRAHEDRON LETTERS, 2008, 49 (19) :3045-3048

[7] PH EFFECTS ON FLUORESCENCE OF UMBELLIFERONE [J].

FINK, DW ;

KOEHLER, WR .

ANALYTICAL CHEMISTRY, 1970, 42 (09) :990-&

[8] Dielectric parameters relevant to microwave dielectric heating [J].

Gabriel, C ;

Gabriel, S ;

Grant, EH ;

Halstead, BSJ ;

Mingos, DMP .

CHEMICAL SOCIETY REVIEWS, 1998, 27 (03) :213-223

[9] Coumarins Preparation by Pechmann Reaction Under Ultrasound Irradiation. Synthesis of Hymecromone as Insecticide Intermediate [J].

Gutierrez-Sanchez, C. ;

Calvino-Casilda, V. ;

Perez-Mayoral, E. ;

Martin-Aranda, R. M. ;

Lopez-Peinado, A. J. ;

Bejblova, M. ;

Cejka, J. .

CATALYSIS LETTERS, 2009, 128 (3-4) :318-322

[10]

Helavi V. B., 2003, J CHEM RES, P279

← 1 2 3 →