118964-06-0

Basic information

• Product Name: (1R)-1,3-dimethyl-2,3,4,5-tetrahydro-1H-1,4-methano-3-benzazepin-8-ol
• CAS NO: 118964-06-0
• Molecular Formula: C₁₃H₁₇NO
• Molecular Weight: 203.2802
• Mol File: 118964-06-0.mol

Chemical Properties

• Boiling Point: 325.4°C at 760 mmHg
• Flash Point: 159.1°C
• Density: 1.148g/cm³
• Vapor Pressure: 0.000121mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: (1R)-1,3-dimethyl-2,3,4,5-tetrahydro-1H-1,4-methano-3-benzazepin-8-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-1,3-dimethyl-2,3,4,5-tetrahydro-1H-1,4-methano-3-benzazepin-8-ol(118964-06-0)
• EPA Substance Registry System: (1R)-1,3-dimethyl-2,3,4,5-tetrahydro-1H-1,4-methano-3-benzazepin-8-ol(118964-06-0)

Safety Data

• Hazardous Substances Data: 118964-06-0(Hazardous Substances Data)

Upstream product

• 128524-63-0 (+)-8-O-methylaphanorphine 
• 929872-83-3 1-methyl-2-(trimethylsilyl)ethyl (1S,3R)-3-[tert-buthoxycarbonyl(methyl)amino]-7-methoxy-2-oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylate 
• 89523-62-6 (4-chlorophenyl)zinc(II) chloride 
• 106-39-8 bromochlorobenzene 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 1301725-78-9 (1R,4R)-N-benzoyl-8-methoxy-1-methyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine 
• 1301725-76-7 (5R)-N-(benzoyl)-5-(4-methoxybenzyl)-3-methylpyrrol-idin-3-ol 
• 1301725-75-6 (5R)-N-(tert-butylsulfonyl)-5-(4-methoxybenzyl)-3-methylpyrrolidin-3-ol 
• 1301725-73-4 (2R)-N-(tert-butylsulfonyl)-1-(4-methoxyphenyl)-3-(2-methyloxiran-2-yl)propan-2-ylamine 
• 1301725-71-2 (4S,Rs)-N-(tert-butylsulfinyl)-5-(4-methoxyphenyl)-2-methylpent-1-en-4-amine 
• 178681-78-2 (R)-2-(3-Methoxy-phenyl)-2-methyl-pentanedioic acid 1-ethyl ester 5-methyl ester 
• 178681-58-8 (R)-2-(3-Methoxy-phenyl)-2-methyl-pentanedioic acid 1-ethyl ester 
• 178681-82-8 (1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-8-one 

Relevant articles and documents

Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters

In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.

Concise route to (-)- and (+)-aphanorphine

This paper presents an application of two recently developed methodologies to the synthesis of naturally occurring (-)-aphanorphine. The first method involves an indium-mediated stereoselective α-aminoallylation of aldehydes to prepare enantioenriched homoallylic amine derivatives. The second is the epoxidation and regioselective opening of the epoxide to afford 2-substituted 3-pyrrolidinols. The synthesis was completed by using a reported Friedel-Crafts alkylation and conventional functional-group manipulation. According to the same route, the O-methyl derivative of unnatural (+)-aphanorphine was prepared from (S)-2-methylpropane-2-sulfinamide. A straightforward synthesis of the marine alkaloid (-)-aphanorphine was accomplished in 9 steps from commercially available starting materials. Indium-mediated stereoselective α-aminoallylation of an aldehyde, pyrrolidin-3-ol formation byintramolecular nucleophilic opening of an epoxide, and intramolecular Friedel-Crafts alkylation are the key steps in this synthesis. Through this methodology, natural (-)-aphanorphine and its enantiomer are affordable. Copyright

An effective route to (-)-aphanorphine using D-tyrosine as a chiral building block

A stereoselective approach toward a naturally occurring alkaloid, (-)-aphanorphine, has been achieved via a series of reactions from Boc-D-tyrosine. Georg Thieme Verlag Stuttgart.

Synthesis of (-)-aphanorphine using a sulfur-directed aryl radical cyclization

Treatment of radical precursor 15a having a vinyl sulfide moiety with Bu3SnH in the presence of AIBN in boiling benzene afforded exclusively the 6-exo cyclization product 16a, whereas similar treatment of the exo-methylene compound 15b gave a mixture of the 6-exo cyclization product 16b and the endo-olefin product 17 formed by a 1,5-hydrogen shift. Based on these findings, the synthesis of (-)-aphanorphine was achieved using a sulfur-directed 6-exo-selective aryl radical cyclization of 22.

Synthesis of (-)-aphanorphine using aryl radical cyclization.

[structure: see text] The synthesis of (-)-aphanorphine was achieved by using Bu(3)SnH-mediated aryl radical cyclization of 1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenylmethyl)-2-methoxycarbonyl-4-(phenylthiomethylene)pyrrolidine, leading to exclusive fo

Asymmetric synthesis of benzylic quaternary carbon center via an enzymatic reaction

(R)-(+)- ((R)-(+)-12) and(S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene((S)-(-)-12) were synthesized based on enantioselective PLE hydrolysis of diethyl 2-(m-methoxyphenyl)-2-methylmalonate. From (R)-(+)-12, (+)-O-Methylaphanorphine (16

The enantioselective total synthesis of natural (-)-aphanorphine

(-)-Aphanorphine, a novel 3-benzazepine alkaloid isolated from the freshwater blue-green alga Aphanizomenon flos-aquae, has been synthesized in an enantioselective fashion.