486-99-7

Basic information

• Product Name: CALYCOTOMINE
• Synonyms: CALYCOTOMINE;[S,(+)]-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-isoquinolinemethanol
• CAS NO: 486-99-7
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.27
• Mol File: 486-99-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 135-139 °C
• Appearance: /
• CAS DataBase Reference: CALYCOTOMINE(CAS DataBase Reference)
• NIST Chemistry Reference: CALYCOTOMINE(486-99-7)
• EPA Substance Registry System: CALYCOTOMINE(486-99-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 486-99-7(Hazardous Substances Data)

Upstream product

• 104058-34-6 (+/-)-8,9-dimethoxy-3-oxo-1,5,6,10b-tetrahydro-3H-oxazolo<4,3-a>isoquinoline 
• 321669-63-0 2α-(2'-bromo-4',5'-dimethoxyphenylmethyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 321669-67-4 N-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-8-aminomenthol 
• 90841-59-1 2-(2-bromo-4,5-dimethoxyphenyl)acetaldehyde 
• 55171-60-3 2-bromo-3,4-dimethoxybenzylaldehyde 
• 204056-59-7 (S)-1-benzyloxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 101053-33-2 (R)-1,5,6,10b-tetrahydro-8,9-dimethoxy-3H-oxazolo<4,3-a>isoquinolin-3-one 
• 486-99-7 (6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolyl)methanol 
• 14022-16-3 (2-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methanol 
• 124201-24-7 1-formyl-4,5-dimethoxyphenylacetic acid methyl ester 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 1370371-82-6 N-(2,2-dimethoxyethyl)-α-(3,4-dimethoxyphenyl)glycine 
• 1370371-81-5 N-(2,2-dimethoxyethyl)-N-benzyl-α-(3,4-dimethoxyphenyl)glycine 
• 1370371-80-4 N-(2,2-diethoxyethyl)-α-(3,4-dimethoxyphenyl)glycine 

Downstream Products

• 98979-80-7 8,9-dimethoxy-3-phenyl-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinoline 
• 87496-32-0 1-Hydroxymethyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbothioic acid phenylamide 
• 87496-35-3 1-Hydroxymethyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbothioic acid cyclohexylamide 
• 93598-34-6 (+/-)-N-methylcalycotomine 
• 1308338-95-5 (S)-(2-(2-fluorobenzyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)(1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone 
• 1308338-32-0 (S)-(2-(2-fluorobenzyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)(1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone 
• 109717-72-8 (-)-threo-N-(ethoxycarbonyl)hydroxynorlaudanosine 
• 109717-73-9 (S)-3,4-dimethoxyphenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl-methanol 
• 6872-27-1 (R)-(+)-xylopinine 

Relevant articles and documents

Continuous-flow enzymatic resolution strategy for the acylation of amino alcohols with a remote stereogenic centre: Synthesis of calycotomine enantiomers

Both enantiomers of calycotomine (R)-5 and (S)-5 were prepared through the CAL-B-catalysed asymmetric O-acylation of N-Boc-protected (6,7-dimethoxy-1,2,3, 4-tetrahydroisoquinolin-1-yl)methanol [(±)-3)]. The optimum conditions for the enzymatic resolution were determined under continuous-flow conditions, while the preparative-scale resolution of (±)-3 was performed as a batch reaction with high enantioselectivity (E >200). The resulting amino alcohol (S)-3 and amino ester (R)-4, obtained with high enantiomeric excess (ee = 99%), were transformed into the desired calycotomine (S)-5 and (R)-5 (ee = 99%). A systematic study was carried out in a continuous-flow system on the O-acylation of tetrahydroisoquinoline amino alcohol homologues (±)-1 to (±)-3 containing a remote stereogenic centre.

Iridium-Catalyzed Enantioselective α-C(sp3)-H Borylation of Azacycles

We herein report an iridium-catalyzed enantioselective α-C(sp3)-H borylation of a wide range of azacycles. The combination of an iridium precursor and a chiral bidentate boryl ligand has been shown to effectively differentiate enantiotropic methylene C-H bonds from a single carbon center, affording a variety of synthetically useful azacycles from readily available starting materials with good to excellent enantioselectivities.

A concise synthesis of tetrahydroisoquinoline-1-carboxylic acids using a Petasis reaction and Pomeranz-Fritsch-Bobbitt cyclization sequence

A sequence of two reactions: the Petasis reaction, in which an aminoacetaldehyde acetal was used as the amine component, followed by Pomeranz-Fritsch-Bobbitt cyclization, has been shown to be a convenient and simple method for the synthesis of tetrahydroisoquinoline-1-carboxylic acids. Using this method several acids have been prepared in good to excellent yields and characterized as hydrochloride salts.