Title:
FUNCTIONALIZED CYANOSILANE AND SYNTHESIS METHOD AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2017/012478
Kind Code:
A1
Abstract:
Disclosed are a functionalized cyanosilane and a synthesis method thereof, wherein the method comprises adding the raw material silane and the cyanogen source MCN to an organic solvent, and synthesizing the functionalized cyanosilane under the conditions of no catalyst or using a metal salt as the catalyst. The functionalized cyanosilane can be used for a reaction in which the classical TMSCN can participate, synthesize important synthetic intermediates such as cyanohydrin, amino alcohol and α-amino cyanogen compounds, and can obtain a better reaction activity and selectivity and the like. In particular, the product, which is obtained by a nucleophilic addition reaction with an aldehyde or a ketone, can also perform an intramolecular reaction under suitable conditions to transfer the functional group carried on the silicon group to other moieties linked to the silicon in the product, thereby improving the synthesis efficiency and atomic economy, and achieving some products that the traditional TMSCN reagent cannot synthesize. Also disclosed are a use of the above-mentioned functionalized cyanosilane in the total synthesis of Leptinotarsa decemlineata aggregation pheromones, and an intermediate compound in the synthesis thereof.
Inventors:
ZHOU JIAN (CN)
ZENG XINGPING (CN)
ZENG XINGPING (CN)
Application Number:
PCT/CN2016/089343
Publication Date:
January 26, 2017
Filing Date:
July 08, 2016
Export Citation:
Assignee:
UNIV EAST CHINA NORMAL (CN)
International Classes:
C07F7/10; C01C3/00; C07C45/44; C07C49/00; C07C49/24; C07F7/18
Foreign References:
| US4429145A | 1984-01-31 |
Other References:
ANDREA RENZETTI ET AL.: "Si- CN Bond Cleavage of Silyl Cyanides by an Iron Catalyst. A New Route of Silyl Cyanide Formation", BULL. CHEM. SOC. JPN., vol. 87, no. 1, 19 October 2013 (2013-10-19), pages 59 - 68, XP055347602, ISSN: 1348-0634
LIU YUNLIN ET AL.: "Organocatalytic Asymmetric Strecker Reaction of Di-and Trifluoromethyl Ketoimines. Remarkable Fluorine Effect", ORGANIC LETTERS, vol. 13, no. 15, 30 June 2011 (2011-06-30), pages 3826 - 3829, XP055347603, ISSN: 1523-7060
TSANG W.C.PETER ET AL.: "Evaluation of Enantiomerically Pure Binaphthol-Based Molybdenum Catalysts for Asymmetric Olefin...Generation and Decomposition of Unsubstituted Molybdacyclobutane Complexes", ORGANOMETALLICS, vol. 20, 29 November 2001 (2001-11-29), pages 5658 - 5669, XP055347604, ISSN: 0276-7333
ZENG XING-PING ET AL.: "Activation of Chiral (Salen)AlCl Complex by Phosphorane for Highly Enantioselective Cyanosilylation of Ketones and Enones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 138, 11 December 2015 (2015-12-11), pages 416 - 42, XP055347605, ISSN: 0002-7863
LIU YUN LIN ET AL.: "Organocatalytic Asymmetric Strecker Reaction of Di-and Trifluoromethyl Ketoimines. Remarkable Fluorine Effect", ORGANIC LETTERS, vol. 13, no. 15, 30 June 2011 (2011-06-30), pages 3826 - 3829, XP055347607, ISSN: 1523-7060
W. ROY JACKSON ET AL.: "Stereoselective Syntheses of Ephedrine and Related 2-Aminoalcohols of High Optical Purity from Protected Cyanohydrins", TETRAHEDRON LETTERS, vol. 31, no. 10, 31 December 1990 (1990-12-31), pages 1447 - 1450, XP001095244, ISSN: 0040-4039
WERONIKA WACLAWCZYK-BIEDRON ET AL.: "Synthesis of the Aggregation Pheromone of the Colorado Potato Beetle from Its Degradation Product", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 25, 30 June 2015 (2015-06-30), pages 3560 - 3563, XP029249464, ISSN: 0960-8940
EMILIA KIURU ET AL.: "2, 2-Disubstituted 4-Acylthio-3-oxobutyl Groups as Esterase-and Thermolabile Protecting Groups of Phosphodiesters", JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 3, 28 December 2012 (2012-12-28), pages 950 - 959, XP055347609, ISSN: 0022-3263
PAUL R ORITIZ DE MONTELLANO ET AL.: "Carboxylic and Phosphate Esters of a-Fluoro Alcohols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 101, no. 8, 11 April 1979 (1979-04-11), pages 2222 - 2224, XP055347612, ISSN: 0002-7863
LIU YUNLIN ET AL.: "Organocatalytic Asymmetric Strecker Reaction of Di-and Trifluoromethyl Ketoimines. Remarkable Fluorine Effect", ORGANIC LETTERS, vol. 13, no. 15, 30 June 2011 (2011-06-30), pages 3826 - 3829, XP055347603, ISSN: 1523-7060
TSANG W.C.PETER ET AL.: "Evaluation of Enantiomerically Pure Binaphthol-Based Molybdenum Catalysts for Asymmetric Olefin...Generation and Decomposition of Unsubstituted Molybdacyclobutane Complexes", ORGANOMETALLICS, vol. 20, 29 November 2001 (2001-11-29), pages 5658 - 5669, XP055347604, ISSN: 0276-7333
ZENG XING-PING ET AL.: "Activation of Chiral (Salen)AlCl Complex by Phosphorane for Highly Enantioselective Cyanosilylation of Ketones and Enones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 138, 11 December 2015 (2015-12-11), pages 416 - 42, XP055347605, ISSN: 0002-7863
LIU YUN LIN ET AL.: "Organocatalytic Asymmetric Strecker Reaction of Di-and Trifluoromethyl Ketoimines. Remarkable Fluorine Effect", ORGANIC LETTERS, vol. 13, no. 15, 30 June 2011 (2011-06-30), pages 3826 - 3829, XP055347607, ISSN: 1523-7060
W. ROY JACKSON ET AL.: "Stereoselective Syntheses of Ephedrine and Related 2-Aminoalcohols of High Optical Purity from Protected Cyanohydrins", TETRAHEDRON LETTERS, vol. 31, no. 10, 31 December 1990 (1990-12-31), pages 1447 - 1450, XP001095244, ISSN: 0040-4039
WERONIKA WACLAWCZYK-BIEDRON ET AL.: "Synthesis of the Aggregation Pheromone of the Colorado Potato Beetle from Its Degradation Product", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 25, 30 June 2015 (2015-06-30), pages 3560 - 3563, XP029249464, ISSN: 0960-8940
EMILIA KIURU ET AL.: "2, 2-Disubstituted 4-Acylthio-3-oxobutyl Groups as Esterase-and Thermolabile Protecting Groups of Phosphodiesters", JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 3, 28 December 2012 (2012-12-28), pages 950 - 959, XP055347609, ISSN: 0022-3263
PAUL R ORITIZ DE MONTELLANO ET AL.: "Carboxylic and Phosphate Esters of a-Fluoro Alcohols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 101, no. 8, 11 April 1979 (1979-04-11), pages 2222 - 2224, XP055347612, ISSN: 0002-7863
Attorney, Agent or Firm:
MSJ LAW OFFICE (CN)
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