174213-76-4

Basic information

• Product Name: (S)-2-(phenoxymethyl)pyrrolidine
• Synonyms: (S)-2-(phenoxymethyl)pyrrolidine;(2S)-2-(phenoxymethyl)pyrrolidine
• CAS NO: 174213-76-4
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.245
• Mol File: 174213-76-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 277.3°C at 760 mmHg
• Flash Point: 109.8°C
• Appearance: /
• Density: 1.017g/cm³
• Vapor Pressure: 0.00456mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: (S)-2-(phenoxymethyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(phenoxymethyl)pyrrolidine(174213-76-4)
• EPA Substance Registry System: (S)-2-(phenoxymethyl)pyrrolidine(174213-76-4)

Safety Data

• Hazardous Substances Data: 174213-76-4(Hazardous Substances Data)

Usage

Description

(S)-2-(phenoxymethyl)pyrrolidine is a chiral chemical compound characterized by a pyrrolidine ring with a phenoxymethyl group attached to the second position. This derivative of pyrrolidine, a five-membered heterocyclic ring with four carbon atoms and one nitrogen atom, features a phenoxymethyl group derived from phenol, which includes a phenol group with a methyl group attached to the oxygen atom. The (S)-stereochemistry of the compound denotes its absolute configuration, and its unique structure, along with the presence of a basic nitrogen atom and a phenol group, may contribute to its potential biological activity.

Uses

Used in Pharmaceutical Industry:
(S)-2-(phenoxymethyl)pyrrolidine is used as a building block for the synthesis of various pharmaceutical compounds due to its unique structure and the presence of both a basic nitrogen atom and a phenol group, which can contribute to the biological activity of the resulting molecules.
Used in Agrochemical Industry:
(S)-2-(phenoxymethyl)pyrrolidine is used as a precursor in the development of agrochemicals, such as pesticides and herbicides, owing to its potential to enhance the biological activity and selectivity of these compounds through its structural features.

InChI:InChI=1/C11H15NO/c1-2-6-11(7-3-1)13-9-10-5-4-8-12-10/h1-3,6-7,10,12H,4-5,8-9H2/t10-/m1/s1

Upstream product

• 174213-51-5 (S)-tert-butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylate 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 76-05-1 trifluoroacetic acid 
• 108-95-2 phenol 
• 113304-84-0 N-benzyl-(S)-proline methyl ester 
• 53912-80-4 (S)-N-benzylprolinol 

Downstream Products

• 220509-98-8 5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione 
• 872254-19-8 (S)-1-(4-Hydroxybenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione 
• 899818-41-8 (S)-1-[4-(2-bromoethoxy)-benzyl]-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione 
• 899818-37-2 (S)-1-(p-tert-butyldimethylsilyloxybenzyl)-5-[1-(2-phenoxymethylpyrrolidinyl)sulfonyl]isatin 
• 220510-28-1 (S)-1-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione 
• 912942-82-6 methanesulfonic acid (S)-2-{4-[2,3-dioxo-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-2,3-dihydro-indol-1-ylmethyl]-phenoxy}ethyl ester 
• 872254-18-7 acetic acid (S)-4-[2,3-dioxo-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-2,3-dihydroindol-1-yl-methyl]phenyl ester 
• 220510-31-6 [2,3-dioxo-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-2,3-dihydro-indol-1-yl]-acetic acid tert-butyl ester 

Relevant articles and documents

Synthesis of Optically Active N -(4-Hydroxynon-2-enyl)pyrrolidines: Key Building Blocks in the Total Synthesis of Streptomyces coelicolor Butanolide 5 (SCB-5) and Virginiae Butanolide A (VB-A)

Starting from 5-methylhexanal and (S)-configured N -propargylprolinol ethers, coupling delivered N -(4-hydroxynon-2-ynyl)prolinol derivatives as mixtures of C4 diastereomers. Resolution of the epimers succeeded after introduction of an (R)-mandelic ester derivative and subsequent HPLC separation. Alternatively, suitable oxidation gave the corresponding alkynyl ketone. Midland reagent controlled diastereoselective reduction afforded a defined configured propargyl alcohol with high selectivity. LiAlH 4reduction and Mosher analyses of the allyl alcohols enabled structure elucidation. The suitably protected products are used as key intermediates in enantioselective Streptomyces γ-butyrolactone signaling molecule total syntheses.

AMIDO-THIOPHENE COMPOUNDS AND THEIR USE

The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain amido-thiophene compounds that, inter alia, inhibit 11 β-hydroxysteroid dehydrogenase type 1 (11 β-HSD1 ). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit 11 β-hydroxysteroid dehydrogenase type 1; to treat disorders that are ameliorated by the inhibition of 11 β-hydroxysteroid dehydrogenase type 1; to treat the metabolic syndrome, which includes disorders such as type 2 diabetes and obesity, and associated disorders including insulin resistance, hypertension, lipid disorders and cardiovascular disorders such as ischaemic (coronary) heart disease; to treat CNS disorders such as mild cognitive impairment and early dementia, including Alzheimer's disease; etc.

5-Pyrrolidinylsulfonyl isatins as a potential tool for the molecular imaging of caspases in apoptosis

Caspases are the unique enzymes responsible for the execution of the cell death program and may represent an exclusive target for the specific molecular imaging of apoptosis in vivo. 5-Pyrrolidinylsulfonyl isatins represent potent nonpeptidyl caspase inhibitors that may be suitable for the development of caspase binding radioligands (CBRs). (S)-5-[1-(2-Methoxymethylpyrrolidinyl) sulfonyl]isatin (7) served as a lead compound for modification of its N-1-position. Corresponding pairs of N-1-substituted 2-methoxymethyl- and 2-phenoxymethylpyrrolidinyl derivatives were examined in vitro by biochemical caspase inhibition assays. All target compounds possess high in vitro caspase inhibition potencies in the nanomolar to subnanomolar range for caspase-3 (Ki = 0.2-56.1 nM). As shown for compound (S)-1-(4-(2-fluoroethoxy) benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin (35), the class of N-1-substituted 5-pyrrolidinylsulfonyl isatins competitively inhibits caspase-3. All caspase inhibitors show selectivity for the effector caspases-3 and -7 in vitro. The 2-methoxymethylpyrrolidinyl versions of the isatins appear to possess superior caspase inhibition potencies in cellular apoptosis inhibition assays compared with the 2-phenoxymethylpyrrolidinyl inhibitors.