(3aS,8S,8aS,8bR)-8-Hydroxy-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione

Base Information

Chemical Name:(3aS,8S,8aS,8bR)-8-Hydroxy-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione
CAS No.:114673-90-4
Molecular Formula:C₁₇H₁₇NO₃
Molecular Weight:283.327
Hs Code.:

Synonyms:(3aS,8S,8aS,8bR)-8-Hydroxy-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione

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Chemical Property of (3aS,8S,8aS,8bR)-8-Hydroxy-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione

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Technology Process of (3aS,8S,8aS,8bR)-8-Hydroxy-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione

There total 7 articles about (3aS,8S,8aS,8bR)-8-Hydroxy-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione 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: 75.0%

: 114673-91-5
(3aS,8S,8aS,8bR)-8-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione

: 114673-90-4
(3aS,8S,8aS,8bR)-8-Hydroxy-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione

Guidance literature:: With acetic acid; In tetrahydrofuran; water; for 72h; Ambient temperature;
DOI:10.1021/ja00222a022

Reference yield: 53.0%

: 941-69-5
N-phenyl-maleimide

: 114614-91-4
3-vinyl-2-cyclopenten-1-ol

: 114673-90-4
(3aS,8S,8aS,8bR)-8-Hydroxy-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione

: 114633-62-4
(2aR,3S,7aR,7bS)-2-Oxo-2,2a,3,4,6,7,7a,7b-octahydro-indeno[1,7-bc]furan-3-carboxylic acid phenylamide

Guidance literature:: In toluene; for 36h; Product distribution; Ambient temperature; also other dienes, also other dienophile (TCNE); cycloaddition selectivity;
DOI:10.1021/ja00222a022

Reference yield:

: 4683-50-5
3-methoxycyclopent-2-enone

: 114673-90-4
(3aS,8S,8aS,8bR)-8-Hydroxy-2-phenyl-4,6,7,8,8a,8b-hexahydro-3aH-cyclopenta[e]isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / tetrahydrofuran / 1 h / -78 °C

2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C

3: 1.) toluene, roomtemp., 36 h; 2.) CH₂Cl₂, 0 deg C, 0.5 h

4: 75 percent / acetic acid / tetrahydrofuran; H₂O / 72 h / Ambient temperature

With water; diisobutylaluminium hydride; sodium fluoride; acetic acid; In tetrahydrofuran; diethyl ether; water;
DOI:10.1021/ja00222a022