171017-19-9

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 3-methyl-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester
• CAS NO: 171017-19-9
• Molecular Formula: C16H21NO3Se
• Molecular Weight: 354.308
• Mol File: 171017-19-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 3-methyl-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 3-methyl-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester(171017-19-9)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 3-methyl-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester(171017-19-9)

Safety Data

• Hazardous Substances Data: 171017-19-9(Hazardous Substances Data)

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 171017-18-8 tert-butyl 3-methyl-2-oxo-1-pyrrolidine-carboxylate 
• 2555-05-7 3-methyl-2-pyrrolidinone 
• 34837-55-3 Phenylselenyl bromide 

Downstream Products

• 171017-24-6 5-[4-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-but-(E)-ylidene]-3-methyl-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 171017-31-5 5-[4-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-but-(Z)-ylidene]-3-methyl-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 215106-54-0 N-Benzyl-4-[4-methyl-5-oxo-1,5-dihydro-pyrrol-(2Z)-ylidene]-butyramide 
• 171017-25-7 N-Benzyl-4-[4-methyl-5-oxo-1,5-dihydro-pyrrol-(2E)-ylidene]-butyramide 
• 462629-66-9 2-{4-[3-methyl-2-oxo-3-(phenylselanyl)-1-pyrrolidinyl]-butyl}1H-isoindole-1,3(2H)-dione 
• 462629-68-1 (E)-N-{4-[3-methyl-2-oxo-3-(phenylselanyl)-1-pyrrolidinyl]butyl}-3-phenyl-2-propenamide 
• 462629-67-0 1-(4-aminobutyl)-3-methyl-3-(phenylselanyl)-2-pyrrolidinone 
• 462629-65-8 3-methyl-3-(phenylselanyl)-2-pyrrolidinone 

Relevant articles and documents

Total synthesis of (+)-ampullicin and (+)-isoampullicin: Two fungal metabolites with growth regulatory activity isolated from Ampulliferina sp. 27

The total synthesis of the growth regulators (+)-ampullicin 1 and (+)-isoampullicin 2 from (R)-(-)-carvone 5 was accomplished by application of an 18-step sequence with 4.5% overall yield. The crucial step of the synthetic strategy lies on the internal displacement of tosylate 13 by means of the lactone enolate. In this way, access was opened to the tricyclic core present in these biologically active sesquiterpenic amides. A Horner-Emmons reaction between the carbaldehyde 16 and the phosphonate 22 led us to the stereoselective preparation of (+)-ampullicin 1. Standard transformation of 1 into the thermodynamically more stable geometric isomer (+)-isoampullicin 2 was trivial. The absolute configuration of both amides was established by X-ray analysis of a sample of synthetic (+)-isoampullicin 2.

Synthesis of α,β-Unsaturated Spirolactams by Intramolecular Cyclization of Endocyclic N-Acyliminium Ions

The synthesis of (+/-)-6-benzyl-3-methyl-3-en-1,6-diazaspirodecane-2,7-dione (18), the spiro moiety of (+/-)-pandamarine has been achieved by oxidative cyclization of the (Z) and (E) isomers of 5-(N-benzyl-4-carboxamido-butylidene)-3-methyl-3-en-pyrrolin-2-one (15a) and (15b).The stereoselectivity exhibited in the intramolecular cyclization by both butylidene precursors has also been discussed.