(-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline

Base Information

Chemical Name:(-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline
CAS No.:1360807-88-0
Molecular Formula:C₁₉H₂₂INO₂
Molecular Weight:423.294
Hs Code.:

Synonyms:(-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline

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Technology Process of (-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline

There total 5 articles about (-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 46.0%

: 1360807-86-8
(2E)-5-(3,4-dimethoxyphenyl)pent-2-en-1-yl methyl carbonate

: 615-43-0
2-iodophenylamine

: 1,2-dimethoxy-4-[(3S)-3-methoxypent-4-en-1-yl]benzene

: 1374459-94-5
N-[(2E)-5-(3,4-dimethoxyphenyl)pent-2-en-1-yl]-2-iodoaniline

: 1360807-88-0
(-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline

Guidance literature:: With bis(1,5-cyclooctadiene)diiridium(I) dichloride; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; In tetrahydrofuran; at 50 ℃; for 6h; optical yield given as %ee; enantioselective reaction;
DOI:10.1002/ejoc.201100981

Reference yield:

: C₁₇H₂₅BO₂

: 1,2-dimethoxy-4-[(3S)-3-methoxypent-4-en-1-yl]benzene

: 1360807-88-0
(-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline

Guidance literature:: Multi-step reaction with 4 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate / water; N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere; Microwave irradiation

2: diisobutylaluminium hydride / tetrahydrofuran; hexane / 2.5 h / -78 °C / Inert atmosphere

3: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4: bis(1,5-cyclooctadiene)diiridium(I) dichloride; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / tetrahydrofuran / 6 h / 50 °C

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenyl-arsane; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; diisobutylaluminium hydride; caesium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1: Suzuki Miyaura coupling;
DOI:10.1002/ejoc.201100981

Reference yield:

: 1200112-80-6
methyl (2E)-5-(3,4-dimethoxyphenyl)-2-pentenoate

: 1,2-dimethoxy-4-[(3S)-3-methoxypent-4-en-1-yl]benzene

: 1360807-88-0
(-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline

Guidance literature:: Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 2.5 h / -78 °C / Inert atmosphere

2: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3: bis(1,5-cyclooctadiene)diiridium(I) dichloride; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / tetrahydrofuran / 6 h / 50 °C

With pyridine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/ejoc.201100981