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

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

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

• 50-00-0 formaldehyd 
• 63-91-2 L-phenylalanine 
• 77497-95-1 (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride 
• 15912-55-7 ethyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 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 
• 67123-97-1 (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 63-91-2 L-phenylalanine 
• 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 

Downstream Products

• 114784-14-4 (S)-4-Benzyloxycarbonylamino-5-((S)-3-hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-5-oxo-pentanoic acid methyl ester 
• 114784-11-1 2-[2-Benzyloxycarbonylamino-3-((S)-3-hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-3-oxo-propyl]-malonic acid dimethyl ester 
• 866186-93-8 N-[2-(3-hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-(1H-indol-3-ylmethyl)-2-oxo-ethyl]-2-nitro-benzenesulfonamide 
• 183958-71-6 tert-butyl (3S)-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 939027-70-0 C₁₇H₁₆FNO₂ 
• 939027-72-2 C₁₈H₁₉NO₃ 
• 939027-73-3 C₁₈H₁₉NO₃ 

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.

Oxazolidines as Intermediates in the Asymmetric Synthesis of 3-Substituted and 1,3-Disubstituted Tetrahydroisoquinolines

A diastereoselective mercury(II)-promoted intramolecular cyclization of unsaturated aldehyde via an oxazolidine to prepare C-3-substituted tetrahydroisoquinoline is disclosed. The C-3 stereogenic center is subsequently exploited to create the C-1 stereocenter by coordination of the nucleophilic reagent to the oxygen atom of oxazolidine. Both cis- and trans-1,3-disubstituted tetrahydroisoquinolines can be readily prepared. In addition, when a cationic rhodium complex was used, intramolecular hydroamination was effected, thus avoiding mercury(II) salts and demercuration. The reaction is general and works well using aliphatic and aromatic aldehydes.

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.

Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands

Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 μM for the cis-dia-stereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4.

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.

Synthesis of (S)-3-aminoethyl-1,2,3,4-tetrahydroisoquinoline (TIQ-diamine) via the Mitsunobu protocol

The synthesis of (S)-3-Aminoethyl-1, 2, 3, 4-tetrahydroisoquinoline (TIQ-diamine) was successfully achieved via the Mitsunobu protocol. The method from earlier reports utilizing aminolysis of commercially available TIQ-amino methyl ester, and reduction of

Utilizing the intramolecular Fukuyama-Mitsunobu reaction for a flexible synthesis of novel heterocyclic scaffolds for peptidomimetic drug design

We report the synthesis of the novel scaffolds pyrazino[1,2-b]isoquinoline and pyrrolo[1,2-a]pyrazine displaying the somatostatin pharmacophores. Both classes of compounds contain a pyrazine heterocycle, which can be prepared in a straightforward manner utilizing an intramolecular Fukuyama-Mitsunobu reaction. As both the families derive from amino acids, they can be accessed in high optical purity.

Isoquinolines useful as analgesics

PCT No. PCT/SE97/00315 Sec. 371 Date Oct. 6, 1997 Sec. 102(e) Date Oct. 6, 1997 PCT Filed Feb. 25, 1997 PCT Pub. No. WO97/31940 PCT Pub. Date Sep. 4, 1997The present invention is directed to compounds that act as analgesics and that have the structure of

3,7-Disubstituted-1,2,3,4-tetrahydroisoquinolines display remarkable potency and selectivity as inhibitors of phenylethanolamine N- methyltransferase versus the α2-adrenoceptor(1a)

3-Hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (4) is a more selective inhibitor (PNMT K(i) = 1.1 μM, α2 K(i) = 6.6 μM, selectivity (α2 K(i)/PNMT K(i)) = 6.0) of phenylethanolamine N-methyltransferase (PNMT, EC 2.1.1.28), with respec

Enantioselective deprotonation of 4-tert-butylcyclohexanone by conformationally constrained chiral lithium amide bases

Conformationally rigid chiral lithium amides based on a tetrahydroisoquinoline motif have been prepared bearing a range of substituents at C1 and C3. These bases were tested in the asymmetric deprotonation reaction of 4-tert-butylcyclohexanone. Although t