(1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

Base Information

Chemical Name:(1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one
CAS No.:108401-51-0
Molecular Formula:C₂₅H₃₂O₅Se
Molecular Weight:491.486
Hs Code.:

Synonyms:(1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

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Chemical Property of (1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

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Technology Process of (1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

There total 10 articles about (1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one 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: 38.0%

: 5707-04-0
Phenylselenyl chloride

: 108425-29-2
(1'S,4'aS,8'aS)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

: 108401-51-0
(1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(00)84950-3

Reference yield:

: 41019-71-0
(+/-)-3,4,8,8a-tetrahydro-5,8a-dimethyl-1,6(2H,7H)-naphthalenedione

: 108401-51-0
(1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

Guidance literature:: Multi-step reaction with 10 steps

1: 84 percent / NaBH₄ / ethanol / 0 °C

2: 75 percent / Li / liquid ammonia

3: 95 percent / p-TsOH / benzene / 80 °C / Dean-Stark

4: 91 percent / PCC / CH₂Cl₂

5: 93 percent / LDA / tetrahydrofuran / -78 °C

6: 83 percent / H₂O₂ / pyridine; CH₂Cl₂ / 0 °C

7: 92 percent / CuI / tetrahydrofuran / -78 °C

8: 78 percent / NaH / tetrahydrofuran / 0 °C

9: 75 percent / p-TsOH / benzene / 80 °C / Dean-Stark

10: 38 percent / LDA / tetrahydrofuran / -78 °C

With sodium tetrahydroborate; copper(l) iodide; dihydrogen peroxide; lithium; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; pyridine; ethanol; dichloromethane; ammonia; benzene;
DOI:10.1016/S0040-4039(00)84950-3

Reference yield:

: 104850-96-6
5,9-Dimethyl-Δ⁵-octalindiol-(1,6)

: 108401-51-0
(1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

Guidance literature:: Multi-step reaction with 9 steps

1: 75 percent / Li / liquid ammonia

2: 95 percent / p-TsOH / benzene / 80 °C / Dean-Stark

3: 91 percent / PCC / CH₂Cl₂

4: 93 percent / LDA / tetrahydrofuran / -78 °C

5: 83 percent / H₂O₂ / pyridine; CH₂Cl₂ / 0 °C

6: 92 percent / CuI / tetrahydrofuran / -78 °C

7: 78 percent / NaH / tetrahydrofuran / 0 °C

8: 75 percent / p-TsOH / benzene / 80 °C / Dean-Stark

9: 38 percent / LDA / tetrahydrofuran / -78 °C

With copper(l) iodide; dihydrogen peroxide; lithium; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; pyridine; dichloromethane; ammonia; benzene;
DOI:10.1016/S0040-4039(00)84950-3