(R)-4-Isopropyl-2-[(2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl]-3-methyl-cyclopent-2-enone

Base Information

Chemical Name:(R)-4-Isopropyl-2-[(2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl]-3-methyl-cyclopent-2-enone
CAS No.:897041-93-9
Molecular Formula:C₂₈H₃₆O₄
Molecular Weight:436.591
Hs Code.:

Synonyms:(R)-4-Isopropyl-2-[(2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl]-3-methyl-cyclopent-2-enone

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Chemical Property of (R)-4-Isopropyl-2-[(2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl]-3-methyl-cyclopent-2-enone

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Technology Process of (R)-4-Isopropyl-2-[(2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl]-3-methyl-cyclopent-2-enone

There total 12 articles about (R)-4-Isopropyl-2-[(2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl]-3-methyl-cyclopent-2-enone 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: 78.0%

: 897041-70-2
(R)-4-Isopropyl-3-methyl-2-trimethylstannanyl-cyclopent-2-enone

: 897041-87-1
(S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

: 897041-93-9
(R)-4-Isopropyl-2-[(2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl]-3-methyl-cyclopent-2-enone

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) chloride; lithium chloride; In dimethyl sulfoxide; at 20 - 60 ℃; for 18h;
DOI:10.1021/ja060847g

Reference yield:

: (1R,4R)-1-Methyl-5-oxo-bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic acid dimethyl ester

: 897041-93-9
(R)-4-Isopropyl-2-[(2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl]-3-methyl-cyclopent-2-enone

Guidance literature:: Multi-step reaction with 10 steps

1.1: 96 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 12 h / 20 °C

2.1: 100 percent / camphorsulfonic acid / 16 h / Heating

3.1: 84 percent / camphorsulfonic acid / CH₂Cl₂ / 36 h

4.1: 65 percent / lithium aluminum hydride / diethyl ether / 5 h / 0 - 20 °C

5.1: 80 percent / pyridinium p-toluenesulfonic acid / CH₂Cl₂ / 19 h

6.1: o-nitrophenylselenocyanate; tri-n-butylphosphine / tetrahydrofuran / 1 h / 0 °C

6.2: 71 percent / aq. H₂O₂ / tetrahydrofuran / 3 h / 0 - 45 °C

7.1: 82 percent / pyridinium p-toluenesulfonic acid / methanol / 2 h

8.1: 69 percent / DDQ / CH₂Cl₂ / 0.5 h / 20 °C

9.1: N,N-dimethylaminopyridine; dicyclohexylacarbodiimide / CH₂Cl₂ / 1.5 h / 0 - 20 °C

10.1: 78 percent / tetrakis(triphenylphosphine)palladium; LiCl; cuprous chloride / dimethylsulfoxide / 18 h / 20 - 60 °C

With dmap; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ortho-nitrophenyl selenocyanate; tributylphosphine; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(l) chloride; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ja060847g

Reference yield:

: (1R,5R)-5-Methyl-3-oxo-2-oxa-bicyclo[3.2.2]non-6-ene-6,7-dicarboxylic acid dimethyl ester

: 897041-93-9
(R)-4-Isopropyl-2-[(2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl]-3-methyl-cyclopent-2-enone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / camphorsulfonic acid / 16 h / Heating

2.1: 84 percent / camphorsulfonic acid / CH₂Cl₂ / 36 h

3.1: 65 percent / lithium aluminum hydride / diethyl ether / 5 h / 0 - 20 °C

4.1: 80 percent / pyridinium p-toluenesulfonic acid / CH₂Cl₂ / 19 h

5.1: o-nitrophenylselenocyanate; tri-n-butylphosphine / tetrahydrofuran / 1 h / 0 °C

5.2: 71 percent / aq. H₂O₂ / tetrahydrofuran / 3 h / 0 - 45 °C

6.1: 82 percent / pyridinium p-toluenesulfonic acid / methanol / 2 h

7.1: 69 percent / DDQ / CH₂Cl₂ / 0.5 h / 20 °C

8.1: N,N-dimethylaminopyridine; dicyclohexylacarbodiimide / CH₂Cl₂ / 1.5 h / 0 - 20 °C

9.1: 78 percent / tetrakis(triphenylphosphine)palladium; LiCl; cuprous chloride / dimethylsulfoxide / 18 h / 20 - 60 °C

With dmap; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ortho-nitrophenyl selenocyanate; tributylphosphine; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(l) chloride; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ja060847g