123620-80-4

Basic information

• Product Name: (1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL
• Synonyms: (1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL;(1S,2R)-1-PHENYL-2-PYRROLIDIN-1-YL-PROPAN-1-OL;(1S,2R)-N,N-TETRAMETHYLENENOREPHEDRINE;Phenylpyrrolidinylpropanol;(IS,2R)-N-Pyrrolidinyl norephedrine HCL;(1S,2R)-1-Phenyl-2-(1-pyrrolidinyl)-1-propanol hydrochloride;(1S,2R)-1-Phenyl-2-(1-pyrrolid;1-Pyrrolidineethanol, .beta.-methyl-.alpha.-phenyl-, (.alpha.S,.beta.R)-
• CAS NO: 123620-80-4
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.3
• Product Categories: chiral;Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 123620-80-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 48 °C
• Boiling Point: 155℃/3mm
• Flash Point: 148.089 °C
• Appearance: White to cream/Powder
• Density: 1.076 g/cm³
• Vapor Pressure: 1.31E-05mmHg at 25°C
• Refractive Index: -14.5 ° (C=2, CHCl3)
• PKA: 13.89±0.20(Predicted)
• CAS DataBase Reference: (1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL(123620-80-4)
• EPA Substance Registry System: (1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL(123620-80-4)

Safety Data

• Hazardous Substances Data: 123620-80-4(Hazardous Substances Data)

Usage

General Description

(1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL is a stereochemically defined organic compound with the molecular formula C15H21NO. It is a chiral molecule with two stereocenters, and it exists as a pair of enantiomers. The compound features a phenyl group and a pyrrolidinyl group attached to a propan-1-ol backbone. This chemical is commonly used as an intermediate in the synthesis of various pharmaceuticals and other organic compounds. It also exhibits some pharmacological activity, acting as an agonist at certain G protein-coupled receptors. Its stereochemistry and molecular structure make it an important compound in the field of drug development and medicinal chemistry.

InChI:InChI=1/C13H19NO.ClH/c1-11(14-9-5-6-10-14)13(15)12-7-3-2-4-8-12;/h2-4,7-8,11,13,15H,5-6,9-10H2,1H3;1H/t11-,13-;/m1./s1

Upstream product

• 628-21-7 1,4-Diiodobutane 
• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 110-52-1 1,4-dibromo-butane 
• 123-75-1 pyrrolidine 
• 4436-22-0 1-phenylpropylene oxide 
• 210558-66-0 (1R,2S)-(+)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol hydrochloride 
• 71-43-2 benzene 
• 1215194-08-3 (S)-(-)-1-phenyl-2-(1-pyrrolidinyl)-1-propanone 
• 19134-50-0 (SR)-(+/-)-1-phenyl-2-(1-pyrrolidinyl)-1-propanone 
• 173676-57-8 1-phenyl-2-(pyrrolidin-1-yl)propan-1-ol 
• 93-55-0 1-phenyl-propan-1-one 
• 492-41-1 (1R,2S)-norephedrine 

Downstream Products

• 209414-27-7 (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol 
• 1224847-71-5 (1R,2S)-1-phenyl-2-(pyrrolidin-1-yl)propyl (2S)-5-[(tert-butoxycarbonyl)amino]-2-(4,5-dihydroimidazo[1,5-a]quinolin-3-ylmethyl)pentanoate 
• 1224847-72-6 (1R,2S)-1-phenyl-2-(pyrrolidin-1-yl)propyl (2R)-5-[(tert-butoxycarbonyl)amino]-2-(4,5-dihydroimidazo[1,5-a]quinolin-3-ylmethyl)pentanoate 
• 1224849-26-6 (1R,2S)-1-phenyl-2-(pyrrolidin-1-yl)propyl (2S)-5-[(tert-butoxycarbonyl)amino]-2-[(7-methyl-4,5-dihydroimidazo[1,5-a]quinolin-3-yl)methyl]pentanoate 
• 1239346-72-5 (2S,3R,7aR)-3-methyl-2-phenylhexahydropyrrolo[2.1-b]oxazole 
• 1403388-28-2 C₁₅H₂₀F₃NO₂Zn 
• 592551-69-4 (1R,2S)-1-phenyl-2-pyrrolidinylpropanamine 
• 166031-45-4 Thioacetic acid S-((1R,2S)-1-phenyl-2-pyrrolidin-1-yl-propyl) ester 

Relevant articles and documents

Chiral Co(II) and Mn(II) catalysts for the 1,3-dipolar cycloaddition reactions of azomethine ylides derived from arylidene imines of glycine

Anhydrous MnBr2 and CoCl2 in conjunction with chiral ephedrine ligands effect substantial asymmetric induction in cycloadducts derived from methyl acrylate and imines of glycine methyl ester. CoCl2 is most effective and gi

Kinetic and computational studies of the composition and structure of activated complexes in the asymmetric deprotonation of cyclohexene oxide by a norephedrine-derived chiral lithium amide

Rational design of efficient chiral lithium amides for enantioselective deprotonations demands understanding of the origin of the selectivity. The mechanism of deprotonation of cyclohexene oxide 1 by lithium (1R,2S)-N-methyl-1-phenyl-2-pyrrolidinylpropanamide 3, which yields (S)-cyclohex-2-en-1-ol (S)-5 in 93% enantiomeric excess in tetrahydrofuran (THF), has been investigated. Kinetics have been used to show that the reaction is first order with respect to the reagents 1 and 3, respectively. NMR investigations of a 6Li and 15N labelled isotopologue of 3 have previously shown that 3 is mainly a dimer of the lithium amide monomer in THF in the initial state. On the basis of these results it is concluded that the rate-limiting activated complexes for the epoxide deprotonation are composed of two molecules of monomer of lithium amide 3 and one molecule of epoxide. Structures and energies of unsolvated and specific THF-solvated reagents and activated complexes have been calculated using PM3 and B3LYP/6-31+G(d). The results are currently being explored for the rational design of chiral lithium amides with improved stereoselectivities.

Enantioselective Conjugate Addition of Catalytically Generated Zinc Homoenolate

We report herein an enantioselective conjugate addition reaction of a zinc homoenolate, catalytically generated via ring opening of a cyclopropanol, to an α,β-unsaturated ketone. The reaction is promoted by a zinc aminoalkoxide catalyst generated from Et2Zn and a chiral β-amino alcohol to afford 1,6-diketones, which undergo, upon heating, intramolecular aldol condensation to furnish highly substituted cyclopentene derivatives with good to high enantioselectivities. The reaction has proved applicable to various 1-substituted cyclopropanols as well as chalcones and related enones. The chiral amino alcohol has proved to enable ligand-accelerated catalysis of the homoenolate generation and its conjugate addition. Positive nonlinear effects and lower reactivity of a racemic catalyst have been observed, which can be attributed to a stable and inactive heterochiral zinc aminoalkoxide dimer.

Method for preparing chiral (1R,2S)-1-phenyl-2-(1-pyrrolidyl)propane-1-alcohol

The invention provides a new method for simply and feasibly synthesizing (1R,2S)-1-phenyl-2-(1-pyrrolidyl)propane-1-alcohol through enzymatic catalysis. The method is easy to operate and mild in condition, an intermediate does not need to be separated, th

A (S)- N - methoxy - methyl -2 - (tetrahydro-pyrrolyl) propionamide and its preparation method and application

The invention discloses a (S)-N-methoxy-methyl-2-(pyrrolidine) propionamide shown as a formula (5). A preparation method is as follows: subjecting a starting material L-alanine to amino protection, reaction with N,O-dimethyl hydroxylamine hydrochloride, removal of amino protecting group, and alkylation; and subjecting the prepared compound shown as (5) to addition elimination and reduction to obtain an Efavirenz chiral ligand shown as the formula (7). The synthetic method of Efavirenz chiral ligand provided by the invention has the advantages of mild reaction conditions, simple operation, high yield and low production cost, and is suitable for industrialized production.