14028-68-3

Usage

Synthesis Reference(s)

Synthesis, p. 474, 1987 DOI: 10.1055/s-1987-33431

InChI:InChI=1/C15H21NO4/c1-4-20-15(17)9-12-11-8-14(19-3)13(18-2)7-10(11)5-6-16-12/h7-8,12,16H,4-6,9H2,1-3H3

Upstream product

• 112342-27-5 (6,7-dimethoxy-3,4-dihydro-2H-isoquinoline-1-ylidene)acetic acid ethyl ester 
• 105-53-3 diethyl malonate 
• 21271-01-2 (6,7-dimethoxy-3,4-dihydro-isoquinolin-1-yl)-acetic acid ethyl ester 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 79641-41-1 N-[2-(3,4-dimethoxyphenyl)ethyl]malonic acid ethyl ester amide 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 1071-46-1 hydrogen ethyl malonate 
• 40129-54-2 (6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-ylidene)-acetic acid ethyl ester 

Downstream Products

• 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 
• 120639-04-5 3-(cyclohexylmethyl)-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol 
• 114795-49-2 3-(cyclohexylmethyl)-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one 
• 17447-42-6 (R)-ethyl 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate 
• 1417826-91-5 (S)-ethyl-2-(6,7-dimethoxy-2-(3-phenylpropanoyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate 
• 52927-74-9 (+/-)-(3t-ethyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-ylidene)-malononitrile 
• 129147-52-0 (4S,11bS)-9,10-Dimethoxy-4-(4-nitro-phenyl)-3-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-1,3,4,6,7,11b-hexahydro-pyrimido[6,1-a]isoquinolin-2-one 
• 129147-62-2 (4S,11bS)-3-Cyclododecylideneamino-9,10-dimethoxy-4-(4-nitro-phenyl)-1,3,4,6,7,11b-hexahydro-pyrimido[6,1-a]isoquinolin-2-one 
• 129147-61-1 (4S,11bS)-3-Cycloheptylideneamino-9,10-dimethoxy-4-(4-nitro-phenyl)-1,3,4,6,7,11b-hexahydro-pyrimido[6,1-a]isoquinolin-2-one 
• 129147-60-0 (4S,11bS)-3-Cyclohexylideneamino-9,10-dimethoxy-4-(4-nitro-phenyl)-1,3,4,6,7,11b-hexahydro-pyrimido[6,1-a]isoquinolin-2-one 
• 129147-59-7 (4S,11bS)-3-Cyclopentylideneamino-9,10-dimethoxy-4-(4-nitro-phenyl)-1,3,4,6,7,11b-hexahydro-pyrimido[6,1-a]isoquinolin-2-one 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 3-alkyl-dihydrotetrabenazine derivatives as vesicular monoamine transporter-2 (VMAT2) ligands

In the search of new probes for in vivo brain imaging of vesicular monoamine transporter type 2 (VMAT2), we have developed an efficient synthesis of a novel series of 3-alkyl-dihydrotetrabenazine (DTBZ) derivatives. The affinity of VMAT2 was evaluated by an in vitro inhibitory binding assay using [125I]-iodovinyl-TBZ or [18F](+)-FP-DTBZ as radioligands in rat striatal tissue homogenates. New DTBZ derivatives exhibited moderate to good binding affinity to VMAT2. Among these new ligands, compound 4b showed the best affinity for VMAT2 (Ki = 5.98 nM) and may be a useful lead compound for future structure-activity studies.

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.

The Reaction of 3,4-Dihydroisoquinolines With Malonic Acid and Its Derivatives

The reaction of various 3,4-dihydroisoquinolines with malonic acid gives the corresponding 1,2,3,4-tetrahydro-1-isoquinolineacetic acids in good yield, while the reaction with cyanoacetic acid and malonic acid half ethyl ester affords 1,2,3,4-tetrahydro-1