97505-87-8

Upstream product

• 1873-77-4 tris-(trimethylsilyl)silane 
• 199276-69-2 (4-azidobut-1-yn-1-yl)benzene 
• 700-91-4 2-phenyl-1-pyrroline 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 97505-84-5 2-Phenyl-1-p-toluolsulfonyl-Δ²-pyrrolin 

Downstream Products

• 76238-10-3 3-(2'-Phenyl-Δ2'-pyrrolin-1'-yl)-acrolein 

Relevant academic research and scientific papers

METHOD FOR PRODUCING OPTICALLY ACTIVE ALPHA-SUBSTITUTED PROLINE

The present invention aims to provide an industrial method practically suitable for producing optically active α-substituted prolines from an acyclic ketone compound by a small number of steps under mild conditions. The present invention relates to a production method of an optically active α-substituted proline (4) and/or an optically active α-substituted prolinamide (5), including (a) reacting an acyclic ketone compound (1) with at least one selected from ammonia, an ammonium salt, primary amine and a salt of primary amine, and a cyanating agent to give a cyclic nitrogen-containing compound (2), (b) hydrating the cyclic nitrogen-containing compound (2) to give an α-substituted prolinamide (3), and (c) resolving the α-substituted prolinamide (3) by one or more of (d) enzymatical hydrolysis, (e) resolution by diastereomeric salt formation, and (f) separation by column chromatography.

Linear or cyclic aminophosphonates as pH markers in phosphorus 31 NMR spectroscopy

Linear or cyclic aminophosphonates are disclosed which are useful as pH markers. A method of using the linear or cyclic aminophosphonates in phosphorus-31 NMR spectroscopy is also disclosed.

A study of vinyl radical cyclization onto the azido group by addition of sulfanyl, stannyl, and silyl radicals to alkynyl azides

Thermal radical reactions of azidoalkynes 2, 8, 14, and 21a-c with thiols 1a-c afford 2-sulfanylvinyl radicals by selective addition of sulfanyl radicals to the triple bond. 1-Phenylvinyl radicals 23 and 30a, as well as vinyl radical 30b, undergo fast 5-cyclization onto the aromatic azide function to give cyclized indoles. In contrast, both 1-phenyl (15, 17) and 1-alkyl (3a,b, 9) vinyl radicals fail to add to their aliphatic azido substituents and exclusively undergo cyclization onto the aromatic sulfanyl ring and H transfer from the thiol precursor. Azidoalkynes 14 and 21a react with Bu3SnH and TMSS under radical conditions to give instead the corresponding amines as a result of preferential attack of Bu3Sn · and (TMS)3Si · radicals on the azido group rather than on the triple bond. Evidence is provided that alkyl radical cyclizations onto azides are not feasible in the presence of thiol, in contrast with the reported utility of these cyclization reactions in the presence of Bu3SnH and TMSS.

Ring Opening and Isomerisation of Δ1-Pyrrolinium Salts

Alkaline hydrolysis of 2-methyl-Δ1-pyrrolinium salts leads to ω-aminopentanone derivatives and the Δ2-pyrroline 4c.Isomerisation of 2-phenyl-Δ1-pyrroline to the Δ2- and Δ3-derivatives is observed when