18881-17-9

Basic information

• Product Name: (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL
• Synonyms: (3S)-3-(Hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline;(3S)-3-(Hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline97%;(S)-1,2,3,4-Tetrahydro-3-isoquinolinylmethanol;(3S)-1,2,3,4-Tetrahydro-3-isoquinolinemethanol;(S)-1,2,3,4-Tetrahydro-3-isoquinolinylmethanol,99%e.e.;3-HYDROXYMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE;(S)-3-HYDROXYMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE;(S)-1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL-METHANOL
• CAS NO: 18881-17-9
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.22
• Product Categories: chiral;Chiral Building Blocks;Heterocyclic Building Blocks;Isoquinolines
• Mol File: 18881-17-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 114-116 °C(lit.)
• Boiling Point: 290.31°C (rough estimate)
• Flash Point: 146.97 °C
• Appearance: Off-white/Crystalline Powder and/or Chunks
• Density: 1.0508 (rough estimate)
• Vapor Pressure: 0.000305mmHg at 25°C
• Refractive Index: -97 ° (C=0.2, MeOH)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 14.57±0.10(Predicted)
• CAS DataBase Reference: (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL(18881-17-9)
• EPA Substance Registry System: (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL(18881-17-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 18881-17-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C10H13NO/c12-7-10-5-8-3-1-2-4-9(8)6-11-10/h1-4,10-12H,5-7H2/p+1/t10-/m0/s1

Upstream product

• 74163-81-8 L-Tic-OH 
• 15912-55-7 ethyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 79815-19-3 methyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate 
• 1510832-00-4 (S)-(2-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol 
• 62708-42-3 o-allylbenzaldehyde 
• 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 
• 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

• 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 
• 939027-70-0 C₁₇H₁₆FNO₂ 
• 939027-72-2 C₁₈H₁₉NO₃ 
• 939027-73-3 C₁₈H₁₉NO₃ 
• 444583-19-1 tert-butyl (3R)-3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Relevant articles and documents

A Highly Effective One-Pot Bicycloannulation Methodology for the Synthesis of Berban and Yohimban Systems Based on Organotin-Mediated Three-Component Coupling (N-Acylative Pentadienylation of C=N Bonds)

A highly effective bicycloannulation methodology for the synthesis of berban and yohimban alkaloid systems is described.Three-component coupling reactions of 2,4-pentadienyltin reagents with C=N bonds and α,β-unsaturated acyl chlorides furnish bicycloannulated products in a one-pot operation.For example, the reactions of 2,4-pentadienyltributyltin(1) with isoquinoline derivatives activated by acryloyl chloride afford the tetracyclic (+/-)-allo-berban systems stereoselectively.Similarly, the reaction of 1 with 3,4-dihydro-β-carboline (11) gives the pentacyclic (+/-)-allo-yohimban system.The reaction is not affected by the stereochemistry of the 2,4-pentadienyltin reagent.A new substituted 2,4-pentadienyltin reagent, 3-(hydroxymethyl)-2,4-pentadienyltrimethyltin (19), is prepared via 3-(hydroxymethyl)pentadienyl dianion.The three-component coupling reaction of 19 with 11 and acryloyl chloride affords the (+/-)-allo-16-(hydroxymethyl)yohimban system, from which (+/-)nitraraine is readily synthesized.In addition, 1,3-asymmetric induction leads to the high diastereoselectivity realized in bicycloannulation (up to 94percent de) when (S)-3--3,4-dihydroisoquinoline (27), which is readily derived from L-phenylalanine, is used in the three-component coupling reaction.

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.

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.