63006-93-9

Usage

Uses

Used in Organic Synthesis:
1,2,3,4-Tetrahydroisoquinoline-3-methanol is used as a synthetic building block for the creation of various organic compounds. Its unique structure allows it to be a versatile starting material for the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydroisoquinoline-3-methanol is used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to be modified and functionalized makes it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 1,2,3,4-Tetrahydroisoquinoline-3-methanol is used as a key component in the development of new pesticides, herbicides, and other crop protection agents. Its unique chemical properties enable the creation of novel molecules with improved efficacy and selectivity.
Used in Dye and Pigment Industry:
1,2,3,4-Tetrahydroisoquinoline-3-methanol is used as a precursor in the synthesis of dyes and pigments due to its light orange solid appearance. Its chemical structure can be modified to produce a variety of colors, making it a valuable asset in the development of new dyes and pigments for various applications, such as textiles, plastics, and inks.
Used in Research and Development:
1,2,3,4-Tetrahydroisoquinoline-3-methanol is also used in research and development laboratories as a model compound for studying various chemical reactions and mechanisms. Its unique structure and properties make it an ideal candidate for exploring new synthetic routes and understanding the reactivity of related compounds.

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

Upstream product

• 15912-55-7 ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate 
• 67123-97-1 (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 62708-42-3 o-allylbenzaldehyde 
• 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 
• 57060-86-3 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 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 
• 63-91-2 L-phenylalanine 

Downstream Products

• 243858-66-4 N-tert-butyloxycarbonyl-1,2,3,4-tetrahydroisoquinoline-3-methanol 
• 1093364-99-8 C₁₉H₂₁NO 
• 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 
• 183958-71-6 tert-butyl (3S)-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1124157-92-1 C₃₄H₂₉BrN₄O₃ 
• 1124157-94-3 C₃₄H₂₉ClN₄O₃ 
• 1124157-98-7 C₂₆H₂₉BrN₄O₃ 
• 1124158-00-4 C₂₆H₂₃ClF₆N₄O₃ 
• 1124158-04-8 C₃₀H₃₇ClN₄O₃ 
• 1124157-41-0 C₃₄H₃₀N₄O₃ 
• 1154425-51-0 C₃₅H₃₂N₄O₃ 
• 1415657-99-6 (S)-3-(((3-iodobenzyl)oxy)methyl)-1,2,3,4-tetrahydroisoquinoline 
• 1415657-96-3 tert-butyl (S)-3-(((3-iodobenzyl)oxy)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Relevant academic research and scientific papers

STEREOCHEMICAL ASPECTS OF PHOTO-SET INDUCED DIRADICAL CYCLIZATION REACTIONS AS A PART OF ISOQUINOLINE ALAKALOID SYNTHETIC STRATEGIES

Studies of the photo-SET induced cyclization reactions of an N-silylbenzyldihydroisoquinolinium salt have uncovered a potentially interesting feature governing stereoselectivities of diradical cyclization reactions.

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.

(η5-Pentamethylcyclopentadienyl)iridium Complex Catalyzed Imine Reductions Utilizing the Biomimetic 1,4-NAD(P)H Cofactor and N-Benzyl-1,4-dihydronicotinamide as the Hydride-Transfer Agent

The interaction between synthetic organometallic complexes and metabolic cofactors has proven to be a newly emerging topic in bioorganometallic chemistry. Thus, the first cationic Cp*Ir-catalyzed (Cp=η5-pentamethylcyclopentadienyl) imine reduction in neutral buffered aqueous medium was examined. The reaction was found to proceed through hydride transfer from NADH as the hydride source at room temperature in air. Cationic Cp*Ir complexes proved to be the most efficient catalysts for this transformation. We also highlighted that the choice of the proton source was essential. The method was subsequently applied to cyclic and noncyclic imines. Eventually, the concept was extended to the reductive alkylation of one amine.

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.

MODULATORS OF REV-ERB

The subject matter herein concerns the identification and development of potent synthetic REV-ERB ligands, such as in vivo agonists and antagonists. These compounds allow for characterization of the effects of modulation of this receptor in vivo specifically on circadian behavior and metabolism, and have suitable characteristics for development of medicinal compounds useful for treatment of malconditions such as diabetes, obesity, atherosclerosis, dyslipidemia, a circadian rhythm disorder, coronary artery disease, bipolar disorder, depression, cancer, a sleep disorder, an anxiety disorder, an addiction disorder, a bone-related disorder such osteoporosis, a skeletal muscle disease, e.g., with compromised exercise capacity, or an autoimmune disorder such as psoriasis, multiple sclerosis, inflammatory bowel disease, and others.

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.