62855-02-1

Basic information

• Product Name: (R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL
• Synonyms: 3(R)-HYDROXYMETHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE;(R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL;(R)-1,2,3,4-Tetrahydroisoquinolyl-methan-3-ol;(3R)-1,2,3,4-Tetrahydroisoquinolin-3-ylmethanol;(R)-(+)-1,2,3,4-Tetrahydro-3-isoquinolinemethanol;(3R)-1,2,3,4-tetrahydroisoquinolin-4-ylMethanol;(R)-(1,2,3,4-tetrahydroisoduinolin-3-yl)-Methanol;(R)-3-Hydroxymethyl-1, 2, 3, 4-tetrahydroisoquinoline
• CAS NO: 62855-02-1
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.22
• Mol File: 62855-02-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 307.9 °C at 760 mmHg
• Flash Point: 147 °C
• Appearance: White/Crystalline
• Density: 1.081 g/cm³
• Vapor Pressure: 0.000305mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 14.57±0.10(Predicted)
• CAS DataBase Reference: (R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL(62855-02-1)
• EPA Substance Registry System: (R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL(62855-02-1)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 62855-02-1(Hazardous Substances Data)

Usage

Description

(R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL, also known as (3R)-1,2,3,4-Tetrahydro-3-isoquinolinemethanol, is an organic compound with a unique structure that features a tetrahydroisoquinoline core and a hydroxyl group attached to a methyl group. This chiral molecule plays a significant role in various chemical reactions and processes, particularly in the field of asymmetric synthesis.

Uses

Used in Pharmaceutical Industry:
(R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL is used as a key intermediate in the asymmetric synthesis of vinylmorpholines, which are important compounds with potential applications in the development of pharmaceuticals and agrochemicals. The asymmetric synthesis is achieved through palladium-catalyzed tandem allylic substitutions with amino alcohols, allowing for the selective formation of desired enantiomers with improved biological activity and reduced side effects.
Used in Chemical Research:
In the field of chemical research, (R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL serves as a valuable building block for the synthesis of various complex organic molecules and natural products. Its unique structure and reactivity make it an attractive candidate for the development of new synthetic methods and strategies, as well as for the exploration of novel chemical transformations and reactions.

InChI:InChI=1/C10H13NO/c12-7-10-5-8-3-1-2-4-9(8)6-11-10/h1-4,10-12H,5-7H2/t10-/m1/s1

Upstream product

• 103733-65-9 (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 62708-42-3 o-allylbenzaldehyde 
• 1510832-00-4 (S)-(2-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol 
• 79815-19-3 methyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate 
• 15912-55-7 ethyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 67123-97-1 (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 63-91-2 L-phenylalanine 
• 77497-95-1 (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride 
• 74163-81-8 L-Tic-OH 
• 15912-56-8 ethyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride 
• 77497-96-2 (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester 
• 50-00-0 formaldehyd 
• 63-91-2 L-phenylalanine 

Downstream Products

• 1510832-00-4 (S)-(2-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol 
• 1033594-26-1 {2-[4-(1-benzyl-piperidin-4-ylamino)-6-(3-fluoro-phenyl)-[1,3,5]rriazin-2-yl]-1,2,3,4-tetrahydro-isoquinolin-(3R)-yl}-methanol 
• 1033594-03-4 3-{4-((3R)-hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-6-[4-(tetrahydropyran-4-yl)-piperazin-1-yl]-[1,3,5]triazin-2-yl}-phenol 
• 1033593-87-1 3-[4-((3R)-hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-6-(4-methyl-piperazin-1-yl)-[1,3,5]triazin-2-yl]-benzoic acid methyl ester 
• 1033594-24-9 {2-[4-(3-fluoro-phenyl)-6-(piperidin-4-ylamino)-[1,3,5]triazin-2-yl]-1,2,3,4-tetrahydro-isoquinolin-(3R)-yl}-methanol 
• 1033594-25-0 {2-[4-(1-benzyl-piperidin-4-ylamino)-6-chloro-[1,3,5]triazin-2-yl]-1,2,3,4-tetrahydro-isoquinolin-(3R)-yl}-methanol 
• 1033594-09-0 C₂₅H₃₁ClN₄O₂Si 
• 1033594-34-1 4-[4-(3-fluoro-phenyl)-6-(3-hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-[1,3,5]triazin-2-ylamino]-piperidine-1-carboxylic acid amide 
• 1033594-32-9 4-[4-(3-fluoro-phenyl)-6-((3R)-hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-[1,3,5]triazin-2-ylamino]-piperidine-1-carboxylic acid methyl ester 
• 1033594-29-4 {2-[4-(3-fluoro-phenyl)-6-(4-morpholin-4-yl-piperidin-1-yl)-[1,3,5]triazin-2-yl]-1,2,3,4-tetrahydro-isoquinolin-(3R)-yl}-methanol 
• 1033594-22-7 {2-[4-(3-fluoro-phenyl)-6-(tetrahydro-pyran-4-yloxy)-[1,3,5]triazin-2-yl]-1,2,3,4-tetrahydro-isoquinolin-(3R)-yl}-methanol 
• 762245-27-2 (S)-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)(3-(hydroxymethyl)-3,4- dihydroisoquinolin-2(1H)-yl)methanone 

Relevant articles and documents

Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides

The preparation of chiral pool-derived nitrone 3 and its use in the protecting-group free, stereoselective synthesis of a range of 1,3-disubstituted tetrahydroisoquinolines is described. Grignard reagent additions to nitrone 3 yielded trans-1,3-disubstituted N-hydroxytetrahydroisoquinolines 6 with good levels of selectivity, while 1,3-dipolar cycloadditions to this nitrone provided access to 3-(2-hydroxyalkyl)isoquinolines 12 as single diastereomers.

Practical and cost-effective manufacturing route for the synthesis of a β-lactamase inhibitor

Compound 1, a potent and irreversible inhibitor of β-lactamases, is in clinical trials with β-lactam antibiotics for the treatment of serious and antibiotic-resistant bacterial infections. A short, scalable, and cost-effective route for the production of this densely functionalized polycyclic molecule is described.

An organogel formed from a cyclic β-aminoalcohol

A new organogelator with unique structural feature of a cyclic β-aminoalcohol is presented as the first example of gelation by aminoalcohol through hydrogen-bonding between hydroxy and amine.