(1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene

Base Information

Chemical Name:(1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene
CAS No.:199180-35-3
Molecular Formula:C₂₃H₃₄O₂
Molecular Weight:342.522
Hs Code.:

Synonyms:(1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene

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Chemical Property of (1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene

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Technology Process of (1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene

There total 15 articles about (1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene 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: 83.0%

: 199180-34-2
(4aS,5R,6S,8aR)-5-(2,5-Dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one

: 74-95-3
1,1-dibromomethane

: 199180-35-3
(1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene

Guidance literature:: With titanium tetrachloride; zinc; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(97)10075-2

Reference yield:

: 113666-06-1
(-)-(4aR)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione

: 199180-35-3
(1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene

Guidance literature:: Multi-step reaction with 15 steps

1: 89 percent / p-TsOH / benzene / Heating

2: NaOMe / methanol / Heating

3: AcOH / ethanol / 15 °C

4: 1.) SOCl₂, pyridine, 2.) DIBAL / 1.) CH₂Cl₂, 0 deg C, 2.) toluene, -78 deg C

5: 99 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

6: hydroquinone / 1,2-dichloro-benzene / 180 °C

7: H₂ / Pd/C / CH₂Cl₂

8: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

9: n-Bu₃P / tetrahydrofuran / Ambient temperature

10: 30percent H₂O₂ / 0 °C

11: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C to 0 deg C

12: 1.) n-BuLi / 1.) Et₂O, -78 deg C, 2.) Et₂O, -78 deg C

13: 88 percent / pyridine / 0 °C

14: 85 percent / H₂ / 10percent Pd/C / methanol / 3800 Torr / Ambient temperature

15: 83 percent / Zn, TiCl₄ / tetrahydrofuran / Ambient temperature

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; tributylphosphine; hydrogen; dihydrogen peroxide; sodium methylate; titanium tetrachloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; acetic acid; hydroquinone; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-benzene; benzene;
DOI:10.1016/S0040-4039(97)10075-2

Reference yield:

: 199180-20-6
5,8a-dimethyl-3,4,8,8a-tetrahydro-2H-spiro[naphthalene-1,2′-[1,3]dioxolan]-6(7H)-one

: 199180-35-3
(1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene

Guidance literature:: Multi-step reaction with 14 steps

1: NaOMe / methanol / Heating

2: AcOH / ethanol / 15 °C

3: 1.) SOCl₂, pyridine, 2.) DIBAL / 1.) CH₂Cl₂, 0 deg C, 2.) toluene, -78 deg C

4: 99 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

5: hydroquinone / 1,2-dichloro-benzene / 180 °C

6: H₂ / Pd/C / CH₂Cl₂

7: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

8: n-Bu₃P / tetrahydrofuran / Ambient temperature

9: 30percent H₂O₂ / 0 °C

10: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C to 0 deg C

11: 1.) n-BuLi / 1.) Et₂O, -78 deg C, 2.) Et₂O, -78 deg C

12: 88 percent / pyridine / 0 °C

13: 85 percent / H₂ / 10percent Pd/C / methanol / 3800 Torr / Ambient temperature

14: 83 percent / Zn, TiCl₄ / tetrahydrofuran / Ambient temperature

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; tributylphosphine; hydrogen; dihydrogen peroxide; sodium methylate; titanium tetrachloride; diisobutylaluminium hydride; ozone; acetic acid; hydroquinone; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-benzene;
DOI:10.1016/S0040-4039(97)10075-2