230642-84-9Relevant articles and documents
A practical pilot-scale synthesis of 4-vinyl-2,3-dihydrobenzofuran using imidate ester chemistry and phase-transfer catalysis
Rao, Meena,Yang, Ming,Kuehner, Daniel,Grosso, John,Deshpande, Rajendra P.
, p. 547 - 550 (2003)
A two-step telescoped synthesis of 4-vinyl-2,3-dihydrobenzofuran (2) was demonstrated using imidate ester chemistry and phase-transfer catalysis. Treatment of 2,3-bis(2-hydroxyethyl)-phenol (1) with the Vilsmeier reagent resulted in an in situ generation of a bis-imidate intermediate 4, which was converted to 4-(2-chloroethyl)-2,3-dihydrobenzofuran (6) via a sequential ring closure and chloride displacement reactions. Further dehydrohalogenation of 6 using a phase-transfer catalyst provided an excellent, cost-effective method to prepare high quality 4-vinyl-2,3-dihydrobenzofuran (2). The yields for the two-step telescoped process ranged from 83 to 90%.
Gram-Scale Synthesis of Chiral Cyclopropane-Containing Drugs and Drug Precursors with Engineered Myoglobin Catalysts Featuring Complementary Stereoselectivity
Bajaj, Priyanka,Sreenilayam, Gopeekrishnan,Tyagi, Vikas,Fasan, Rudi
, p. 16110 - 16114 (2016/12/26)
Engineered hemoproteins have recently emerged as promising systems for promoting asymmetric cyclopropanations, but variants featuring predictable, complementary stereoselectivity in these reactions have remained elusive. In this study, a rationally driven strategy was implemented and applied to engineer myoglobin variants capable of providing access to 1-carboxy-2-aryl-cyclopropanes with high trans-(1R,2R) selectivity and catalytic activity. The stereoselectivity of these cyclopropanation biocatalysts complements that of trans-(1S,2S)-selective variants developed here and previously. In combination with whole-cell biotransformations, these stereocomplementary biocatalysts enabled the multigram synthesis of the chiral cyclopropane core of four drugs (Tranylcypromine, Tasimelteon, Ticagrelor, and a TRPV1 inhibitor) in high yield and with excellent diastereo- and enantioselectivity (98–99.9% de; 96–99.9% ee). These biocatalytic strategies outperform currently available methods to produce these drugs.
Preparation method of 4-vinyl-2,3-dihydrobenzene
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Paragraph 0061; 0062, (2017/03/08)
The invention provides a preparation method of 4-vinyl-2,3-dihydrobenzene. The preparation method comprises the following steps that under the alkaline condition, a compound (1) and a sulfonylation reagent take a reaction to obtain a compound (2); in the inert gas atmosphere, the compound (2) takes a reaction under the alkaline condition to obtain a product (3). The route is simple; three steps of reactions including sulphonate hydrolysis, cyclization and elimination of the compound (2) are skillfully completed in one pot, so that the reaction efficiency is greatly improved; the reaction steps are shortened; the operation work procedure is simplified; the high-purity 4-vinyl-2,3-dihydrobenzene (3) is prepared almost at a quantitative yield. The synthesis method has the advantages that the reaction conditions are mild; the operation is simple and convenient; the yield is high; the selectivity is good; the production cost is low; the product quality is good; the method is suitable for industrial production; great practical application values and social economical benefits are realized. The structural formula is shown as the accompanying drawing.
