Synthesis of Vitamin K1 and K1-Chromanol by Friedel-Crafts Alkylation in Heterogeneous Catalysis

被引：31

作者：

Coman, Simona M. ^{[1
,2
]}

Parvulescu, Vasile I. ^{[2
]}

Wuttke, Stefan ^{[1
]}

Kemnitz, Erhard ^{[1
]}

机构：

[1] Humboldt Univ, Inst Chem, D-12489 Berlin, Germany

[2] Univ Bucharest, Dept Chem Technol & Catalysis, Fac Chem, Bucharest 030016, Romania

来源：

CHEMCATCHEM | 2010年 / 2卷 / 01期

关键词：

fluorides; green chemistry; heterogeneous catalysis; Lewis acids; vitamins; SOL-GEL SYNTHESIS; METAL FLUORIDES; DERIVATIVES;

D O I：

10.1002/cctc.200900205

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The partly hydroxylated MgF2 and AIF(3) materials are efficient and selective catalysts for the preparation of two important members of the vitamin K class: vitamin K, and vitamin K-1-chromanol. The high activity in combination with high selectivity in one of the target products os due to both the acidic strength and the synergistic effect of the presence of both optimized Bronsted and Lewis sites. Therefore, the-best catalyst for a target product can be obtained through a very simple tuning of the acidic properties of the material. Moreover, the results obtained in the present study (Y-vitamin k1-57.8% and Yvitamin k1-chromanol-71.4% are also very encouraging from the environment standpoint as green elements are introduced by using solid catalysts and a biphasic solvent system.

引用

页码：92 / 97

页数：6

共 16 条

[1] The antihemorrhagic activity of sulfonated derivatives of 2-methylnaphthalene [J].

Baker, BR ;

Davies, TH ;

McElroy, L ;

Carlson, GH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :1096-1101

[2] Catalytic Performance of Nanoscopic, Aluminium Trifluoride-Based Catalysts in the Synthesis of (all-rac)-α-Tocopherol [J].

Coman, S. M. ;

Wuttke, S. ;

Vimont, A. ;

Daturi, M. ;

Kemnitz, E. .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (16) :2517-2524

[3] Cyclisation of citronellal over heterogeneous inorganic fluorides-highly chemo- and diastereoselective catalysts for (±)-isopulegol [J].

Coman, Simona M. ;

Patil, Pratap ;

Wuttke, Stefan ;

Kemnitz, Erhard .

CHEMICAL COMMUNICATIONS, 2009, (04) :460-462

[4] THE SYNTHESIS OF VITAMIN-K [J].

HIRSCHMANN, R ;

MILLER, R ;

WENDLER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (18) :4592-4594

[5] Practical synthesis of (R)-(+)-6-(1,4-dimethoxy-3-methyl-2-naphthyl)-6-(4-hydroxyphenyl)hexanoic acid:: a key intermediate for a therapeutic drug for neurodegenerative diseases [J].

Ito, T ;

Ikemoto, T ;

Yamano, T ;

Mizuno, Y ;

Tomimatsu, K .

TETRAHEDRON-ASYMMETRY, 2003, 14 (22) :3525-3531

[6] Amorphous metal fluorides with extraordinary high surface areas [J].

Kemnitz, E ;

Gross, U ;

Rudiger, S ;

Shekar, CS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4251-4254

[7]

Kemnitz E., 2003, ANGEW CHEM, V115, P4383, DOI DOI 10.1016/J.JFLUCHEM.2006.11.006

[8]

Mayer H., 1971, VITAMINS, VIII

[9] SYNTHESIS AND STOPPED-FLOW INVESTIGATION OF ANTIOXIDANT ACTIVITY OF TOCOPHEROLS - FINDING OF NEW TOCOPHEROL DERIVATIVES HAVING THE HIGHEST ANTIOXIDANT ACTIVITY AMONG PHENOLIC ANTIOXIDANTS [J].

MUKAI, K ;

OKABE, K ;

HOSOSE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :557-560

[10] Synthesis of α-tocopherol (vitamin E), vitamin K1-chromanol, and their analogs in the presence of aluminosilicate catalysts Tseokar-10 and Pentasil [J].

Odinokov, VN ;

Spivak, AV ;

Emelyanova, GA ;

Mallyabaeva, MI ;

Nazarova, OV ;

Dzhemilev, UM .

ARKIVOC, 2003, :101-118

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