(4aR^*,6S^*,7S^*,9R^*)-3,4,6,7,8,9,10,11-octahydro-7-hydroxy-6-(phenylseleno)-4a,9-methano-4H-benzocyclononene-1,12(5H)-dione

Base Information

• Chemical Name: (4aR^*,6S^*,7S^*,9R^*)-3,4,6,7,8,9,10,11-octahydro-7-hydroxy-6-(phenylseleno)-4a,9-methano-4H-benzocyclononene-1,12(5H)-dione
• CAS No.: 88671-34-5
• Molecular Formula: C₂₀H₂₂O₃Se
• Molecular Weight: 389.353

Synonyms:(4aR^*,6S^*,7S^*,9R^*)-3,4,6,7,8,9,10,11-octahydro-7-hydroxy-6-(phenylseleno)-4a,9-methano-4H-benzocyclononene-1,12(5H)-dione

Chemical Property of (4aR^*,6S^*,7S^*,9R^*)-3,4,6,7,8,9,10,11-octahydro-7-hydroxy-6-(phenylseleno)-4a,9-methano-4H-benzocyclononene-1,12(5H)-dione

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Technology Process of (4aR^*,6S^*,7S^*,9R^*)-3,4,6,7,8,9,10,11-octahydro-7-hydroxy-6-(phenylseleno)-4a,9-methano-4H-benzocyclononene-1,12(5H)-dione

There total 3 articles about (4aR^*,6S^*,7S^*,9R^*)-3,4,6,7,8,9,10,11-octahydro-7-hydroxy-6-(phenylseleno)-4a,9-methano-4H-benzocyclononene-1,12(5H)-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:

(1S,9R)-4-Methoxy-tricyclo[7.4.1.01,6]tetradeca-3,5,11-trien-14-one (88671-29-8) → (4aR*,6S*,7S*,9R*)-3,4,6,7,8,9,10,11-octahydro-7-hydroxy-6-(phenylseleno)-4a,9-methano-4H-benzocyclononene-1,12(5H)-dione (88671-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.5 N hydrochloric acid / tetrahydrofuran / Ambient temperature

2: 1) bromine, AgOCOCF₃; 2) sodium bicarbonate / 1) THF, 30 min, -78 deg C; 2) H₂O, MeOH, RT, overnight

With hydrogenchloride; bromine; silver trifluoroacetate; sodium hydrogencarbonate; In tetrahydrofuran;

DOI:10.1021/ja00317a043

Reference yield:

(S)-8a-((Z)-4-Chloro-but-2-enyl)-6-methoxy-3,4,8,8a-tetrahydro-2H-naphthalen-1-one (88671-28-7) → (4aR*,6S*,7S*,9R*)-3,4,6,7,8,9,10,11-octahydro-7-hydroxy-6-(phenylseleno)-4a,9-methano-4H-benzocyclononene-1,12(5H)-dione (88671-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 10.3 g / KH / 2-methyl-propan-2-ol; 1,2-dimethoxy-ethane / 2 h, -78 deg C; RT, overnight

2: 1.5 N hydrochloric acid / tetrahydrofuran / Ambient temperature

3: 1) bromine, AgOCOCF₃; 2) sodium bicarbonate / 1) THF, 30 min, -78 deg C; 2) H₂O, MeOH, RT, overnight

With hydrogenchloride; bromine; silver trifluoroacetate; potassium hydride; sodium hydrogencarbonate; In tetrahydrofuran; 1,2-dimethoxyethane; tert-butyl alcohol;

DOI:10.1021/ja00317a043

Reference yield:

diphenyl diselenide (1666-13-3) + (4aR*,9R*)-3,4,8,9,10,11-hexahydro-4a,9-methano-4aH-benzocyclononene-2,12(5H)-dione (88671-30-1) → (4aR*,6S*,7S*,9R*)-3,4,6,7,8,9,10,11-octahydro-7-hydroxy-6-(phenylseleno)-4a,9-methano-4H-benzocyclononene-1,12(5H)-dione (88671-34-5)

Guidance literature:

With bromine; silver trifluoroacetate; sodium hydrogencarbonate; Yield given. Multistep reaction; 1) THF, 30 min, -78 deg C; 2) H₂O, MeOH, RT, overnight;

DOI:10.1021/ja00317a043

upstream raw materials:

diphenyl diselenide

(4aR^*,9R^*)-3,4,8,9,10,11-hexahydro-4a,9-methano-4aH-benzocyclononene-2,12(5H)-dione

(1S,9R)-4-Methoxy-tricyclo[7.4.1.0^1,6]tetradeca-3,5,11-trien-14-one

(S)-8a-((Z)-4-Chloro-but-2-enyl)-6-methoxy-3,4,8,8a-tetrahydro-2H-naphthalen-1-one

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