(S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate

Base Information

Chemical Name:(S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate
CAS No.:1264519-79-0
Molecular Formula:C₃₂H₂₇NO₄
Molecular Weight:489.571
Hs Code.:

Synonyms:(S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate

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Chemical Property of (S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate

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Technology Process of (S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate

There total 3 articles about (S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate 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: 97.0%

: 1264519-10-9
phenanthren-9-yl 2-(4-cyanophenyl)acrylate

: 189078-68-0
tert-butyl buta-2,3-dienoate

: 1264519-79-0
(S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate

Guidance literature:: With 1,1,1-trichloro-2-methyl-propan-2-yl (S)-1-[(2R,3S)-3-(tert-butyldiphenylsilyloxy)-1-(diphenylphosphino)-butan-2-ylamino]-3,3-dimethyl-1-oxobutan-2-ylcarbamate; In toluene; at 20 ℃; for 0.166667h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ja1106282

Reference yield:

: 934476-97-8
2-(4-cyanophenyl)acrylic acid

: 1264519-79-0
(S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C

2: 1,1,1-trichloro-2-methyl-propan-2-yl (S)-1-[(2R,3S)-3-(tert-butyldiphenylsilyloxy)-1-(diphenylphosphino)-butan-2-ylamino]-3,3-dimethyl-1-oxobutan-2-ylcarbamate / toluene / 0.17 h / 20 °C / Inert atmosphere

With dmap; 1,1,1-trichloro-2-methyl-propan-2-yl (S)-1-[(2R,3S)-3-(tert-butyldiphenylsilyloxy)-1-(diphenylphosphino)-butan-2-ylamino]-3,3-dimethyl-1-oxobutan-2-ylcarbamate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; toluene;
DOI:10.1021/ja1106282

Reference yield:

: 409359-86-0
ethyl 2-(4-cyanophenyl)propenoate

: 1264519-79-0
(S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydroxide / water / 1 h / Reflux

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C

3: 1,1,1-trichloro-2-methyl-propan-2-yl (S)-1-[(2R,3S)-3-(tert-butyldiphenylsilyloxy)-1-(diphenylphosphino)-butan-2-ylamino]-3,3-dimethyl-1-oxobutan-2-ylcarbamate / toluene / 0.17 h / 20 °C / Inert atmosphere

With dmap; 1,1,1-trichloro-2-methyl-propan-2-yl (S)-1-[(2R,3S)-3-(tert-butyldiphenylsilyloxy)-1-(diphenylphosphino)-butan-2-ylamino]-3,3-dimethyl-1-oxobutan-2-ylcarbamate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In dichloromethane; water; toluene;
DOI:10.1021/ja1106282