51452-46-1

Basic information

• Product Name: 1-Isoquinolineethanol,1,2,3,4-tetrahydro-6,7-dimethoxy-
• Synonyms: 1-Isoquinolineethanol,1,2,3,4-tetrahydro-6,7-dimethoxy-
• CAS NO: 51452-46-1
• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.29
• Product Categories: Drug Intermediates
• Mol File: 51452-46-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 399.6°C at 760 mmHg
• Flash Point: 195.5°C
• Appearance: /
• Density: 1.101g/cm³
• Vapor Pressure: 4.2E-07mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: 1-Isoquinolineethanol,1,2,3,4-tetrahydro-6,7-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Isoquinolineethanol,1,2,3,4-tetrahydro-6,7-dimethoxy-(51452-46-1)
• EPA Substance Registry System: 1-Isoquinolineethanol,1,2,3,4-tetrahydro-6,7-dimethoxy-(51452-46-1)

Safety Data

• Hazardous Substances Data: 51452-46-1(Hazardous Substances Data)

Usage

Chemical Class

Isoquinoline Alkaloids

Subclass

Tetrahydroisoquinoline Alkaloid

Natural Occurrence

Found in various plant species, including the bark of the magnolia tree

Pharmacological Properties

Anti-inflammatory, antioxidant, neuroprotective, potential analgesic and anxiolytic effects

Potential Therapeutic Applications

Treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's

Ongoing Research

To explore the full range of its biological activities and potential therapeutic applications.

InChI:InChI=1/C13H19NO3/c1-16-12-7-9-3-5-14-11(4-6-15)10(9)8-13(12)17-2/h7-8,11,14-15H,3-6H2,1-2H3

Upstream product

• 14028-68-3 ethyl 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate 
• 112342-27-5 (6,7-dimethoxy-3,4-dihydro-2H-isoquinoline-1-ylidene)acetic acid ethyl ester 
• 79641-41-1 N-[2-(3,4-dimethoxyphenyl)ethyl]malonic acid ethyl ester amide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 14028-71-8 9,10-dimethoxy-4-phenyl-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline 
• 87496-36-4 1-(2-Hydroxy-ethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid phenylamide 
• 87496-33-1 1-(2-Hydroxy-ethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbothioic acid phenylamide 
• 87496-34-2 1-(2-Hydroxy-ethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbothioic acid cyclohexylamide 
• 627862-69-5 (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 740817-44-1 1-(2-hydroxy-ethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester 
• 627862-68-4 1-(S)-N-carbobenzyloxy-O-triisopropylsilyl-2-(6,7-dimethoxy-3,4-dihydro-2H-isoquinoline-1-yl)ethanol 
• 628723-98-8 1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline 
• 87496-41-1 [6,7-Dimethoxy-4,4a,9,10-tetrahydro-3H-2-oxa-10a-aza-phenanthren-(1Z)-ylidene]-phenyl-amine 

Relevant articles and documents

Enantioselective total syntheses of the Ipecacuanha alkaloid emetine, the Alangium alkaloid tubulosine and a novel benzoqainolizidine alkaloid by using a domino process

The first enantioselective syntheses of the Ipecacuanha alkaloid emetine (1) and the Alangium alkaloid tubulosine (2) is described employing a domino Knoevenagel/hetero-Diels-Alder reaction and an enantioselective catalytic transfer hydrogenation of imines as key steps. Thus, hydrogenation of the imine 15 with the catalyst (R,R)-16 gives the tetrahydroisoquinoline 14 with 95% ee which was transformed into the aldehyde (1S)-7. The three-component domino reaction of (1S)-7 with 6 and 8 led to 19, which in a second domino process was treated with K2CO3 in methanol followed by a hydrogenation to give the benzoquinolizidine 4 together with the diastereomers 22 and 23 in a overall yield of 66%. Further transformation of 4 with the amines 3 and 5 yielded enantiopure emetine (1) and tubulosine (2), respectively. In addition, starting from 19 the novel benzoquinolizidine alkaloid 34 was synthesised; this compound resembles the vallesiachotamine alkaloid dihydroantirhin 31, which has not been isolated so far but probably must also exist in nature.