61160-12-1

Basic information

• Product Name: 1H-Pyrrolo[1,2-c]imidazol-1-one,hexahydro-3-thioxo-,(7aS)-(9CI)
• Synonyms: 1H-Pyrrolo[1,2-c]imidazol-1-one,hexahydro-3-thioxo-,(7aS)-(9CI)
• CAS NO: 61160-12-1
• Molecular Formula: C₆H₈N₂OS
• Molecular Weight: 156.2055
• Product Categories: PYRROLE
• Mol File: 61160-12-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.44g/cm³
• Refractive Index: 1.673
• PKA: 11.04±0.20(Predicted)
• CAS DataBase Reference: 1H-Pyrrolo[1,2-c]imidazol-1-one,hexahydro-3-thioxo-,(7aS)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[1,2-c]imidazol-1-one,hexahydro-3-thioxo-,(7aS)-(9CI)(61160-12-1)
• EPA Substance Registry System: 1H-Pyrrolo[1,2-c]imidazol-1-one,hexahydro-3-thioxo-,(7aS)-(9CI)(61160-12-1)

Safety Data

• Hazardous Substances Data: 61160-12-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H8N2OS/c9-5-4-2-1-3-8(4)6(10)7-5/h4H,1-3H2,(H,7,9,10)/t4-/m0/s1

Upstream product

• 147-85-3 L-proline 
• 17356-08-0 thiourea 
• 609-36-9 rac-Pro-OH 
• 367906-67-0 N-cyanoproline methyl ester 
• 1147550-11-5 ammonium thiocyanate 
• 108-24-7 acetic anhydride 
• 1074-79-9 N-Acetyl-DL-prolin 
• 532-55-8 Benzoyl isothiocyanate 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 

Relevant articles and documents

Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate

We propose a new concept of the triple role of protic ionic liquids with nucleophilic anions: a) a regenerable solvent, b) a Br?nsted acid inducing diverse transformations via general acid catalysis, and c) a source of a nucleophile. The efficiency of this strategy was demonstrated using thiocyanate-based protic ionic liquids for the ring-opening of donor-acceptor cyclopropanes. A wide variety of activated cyclopropanes were found to react with 1-methylimidazolium thiocyanate under mild metal-free conditions via unusual nitrogen attack of the ambident thiocyanate ion on the electrophilic center of the three-membered ring affording pyrrolidine-2-thiones bearing donor and acceptor substituents at the C(5) and C(3) atoms, respectively, in a single time-efficient step. The ability of 1-methylimidazolium thiocyanate to serve as a triplex reagent was exemplarily illustrated by (4+2)-annulation with 1-acyl-2-(2-hydroxyphenyl)cyclopropane, epoxide ring-opening and other organic transformations.

Catalytic enantioselective synthesis of N,Cα,Cα-trisubstituted α-amino acid derivatives using 1H-imidazol-4(5H)-ones as key templates

Abstract 1H-Imidazol-4(5H)-ones are introduced as novel nucleophilic α-amino acid equivalents in asymmetric synthesis. These compounds not only allow highly efficient construction of tetrasubstituted stereogenic centers, but unlike hitherto known templates, provide direct access to N-substituted (alkyl, allyl, aryl) α-amino acid derivatives. A BB method: 1H-imidazol-4(5H)-ones serve as effective and easily available α-amino acid surrogates for the catalytic and highly diastereo- and enantioselective direct construction of N-substituted quaternary α-amino acid derivatives. The reaction is catalyzed by a Br?nsted base (BB) and proceeds with different Michael acceptors. EWG=electron-withdrawing group.

A simple synthesis of 2-thiohydantoins

2-Thiohydantoin derivatives are produced by heating a mixture of thiourea and an a-amino acid. The method described offers the advantages of simplicity, low cost, easy work-up and scalability.