13450-58-3Relevant articles and documents
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Leete
, p. 4433 (1968)
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Hu et al.
, p. 79,84 (1974)
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A short and efficient synthesis of unnatural (R)-nicotine
Girard,Robins,Villieras,Lebreton
, p. 9245 - 9249 (2000)
A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). (C) 2000 Elsevier Science Ltd.
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Craig
, p. 2854 (1933)
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Zymalkowski,Trenktrog
, p. 9,13 (1959)
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ABILITY OF A NICOTIANA PLUMBAGINIFOLIA CELL SUSPENSION TO DEMETHYLATE NICOTINE INTO NORNICOTINE
Manceau, Francoise,Fliniaux, Marc-Andre,Jacquin-Dubreuil, Annie
, p. 2671 - 2674 (1989)
A cell suspension of Nicotiana plumbaginifolia which does not accumulate tobacco alkaloids was found to keep the ability to demethylate nicotine into nornicotine.The highest bioconversion yield was 53.2 percent.The influence of some environmental factors upon the reaction has been studied.In particular, it appears that light enhances the catalytic activity of the cells which leads to the hypothesis that this metabolic step of tobacco alkaloids is bound to photodependent systems.
Preparation method of chiral nicotine synthesized by chiral tert-butyl sulfinamide
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, (2021/09/29)
The preparation method comprises the following steps: 3 - pyridine formaldehyde and chiral tert-butyl sulfinamide are subjected to condensation reaction under the action of titanate. Further, magnesium bromide reacts with (1, 3 - dioxan -2 -ethyl) magnesium bromide. Cyclization is carried out under acidic conditions. Finally, by reduction and amine methylation, chiral nicotine is obtained. The method has the advantages of short reaction route, easily available and cheap raw materials, high yield of chiral nicotine generated by reaction, high ee-value and reduced production cost of chiral nicotine.
Preparation method of nicotine and intermediate thereof
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, (2021/06/02)
The invention relates to a preparation method of nicotine and an intermediate thereof, wherein the intermediate has a structure as shown in a formula (II), X1, X2 and X3 are respectively and independently CR2R3, R1 is a C1-6 alkyl group, and R2 and R3 are each independently H or a C1-6 alkyl group. According to the invention, the preparation method of the nicotine and the intermediate thereof has the advantages of simple operation, mild reaction conditions, easily available raw materials, and high conversion rate, can effectively reduce the production cost of the nicotine, and has the potential of industrial production, and each reaction can be directly post-fed through simple post-treatment basically.
Method for synthesizing chiral nicotine from butyrolactone
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Paragraph 0057-0059, (2021/11/03)
The invention discloses a method for synthesizing chiral nicotine from butyrolactone. The fumarates and γ - butyrolactone are condensed under the action of a basic catalyst to yield 4 - chloro -1 - (3 - pyridine) -1 -butanone by reaction with hydrochloric acid and reacted with a chlorination reagent to produce (- B -) S (-4 -1 -dichlorobutyl) pyridine which is reacted with an amine reagent under basic conditions to give (-3 -) -1 -methyl nicotine and (S)-3 - nicotinic acetylbutanolamines obtained by the reaction with the aminating reagent under an alkaline condition to produce a chiral hydroxy S S group - (1) S- methylnicotine or a (4 -) S nicotinic acid. The application can determine whether a methylation reaction is needed according to the type of amination reagent. The yield of (S)- nicotine was high.
