(3S,6S,SS,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

Base Information

Chemical Name:(3S,6S,SS,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene
CAS No.:114790-66-8
Molecular Formula:C₂₁H₂₆O₂S
Molecular Weight:342.502
Hs Code.:

Synonyms:(3S,6S,SS,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

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Chemical Property of (3S,6S,SS,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

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Technology Process of (3S,6S,SS,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

There total 16 articles about (3S,6S,SS,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene 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: 82.0%

: 114790-65-7
(3S,6S,SS,1'S,2'R)-3-<2-<(benzoyloxy)methyl>-1-methyl-3-oxocyclopentyl>-3,6-dimethyl-1-(phenylsulfinyl)cyclohexene

: 114790-66-8
(3S,6S,SS,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

Guidance literature:: With 2,6-dichloro-benzonitrile; In toluene; at 80 ℃; for 1.5h;
DOI:10.1021/ja00222a036

Reference yield:

: 114790-65-7,114883-10-2
(3S,6S,SR,1'S,2'R)-3-<2-<(benzoyloxy)methyl>-1-methyl-3-oxocyclopentyl>-3,6-dimethyl-1-(phenylsulfinyl)cyclohexene

: 114790-66-8,114790-86-2
(3S,6S,SR,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

Guidance literature:: With 2,6-dichloro-benzonitrile; In toluene; at 80 ℃; for 1.5h;
DOI:10.1021/ja00222a036

Reference yield:

: 2758-18-1
3-Methyl-2-cyclopenten-1-one

: 114790-66-8
(3S,6S,SS,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) Br₂/Et₃N, 2.) p-toluenesulfonic acid / 1.) CCl₄, 2.) benzene, reflux

2: 1.) n-BuLi, 3.) oxalic acid / 1.) THF, hexane, -78 deg C, 45 min; 2.) THF, hexane, -78 deg C, 30 min, 25 deg C, 15 min; 3.) CH₂Cl₂-water, 25 deg C, 12 h

3: 1.) LDA / 1.) THF, -78 deg C, 10 min; 2.) THF, -78 deg C, 15 min

4: 67 percent / LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 2.) 25 deg C, 18 h

5: 70 percent / triethylamine / acetonitrile / 2 h / -10 °C

6: 84 percent / 3A molecular sieves, PCC / CH₂Cl₂ / 3 h / 25 °C

7: 82 percent / DBN / toluene / 1.5 h / 80 °C

With lithium borohydride; n-butyllithium; 2,6-dichloro-benzonitrile; 3 A molecular sieve; bromine; oxalic acid; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ja00222a036