(-)-4α-acetoxy-1-ethenyl-2-(7-methoxy-Δ³-isochromenyl)-1β-methylcyclohexane

Base Information

Chemical Name:(-)-4α-acetoxy-1-ethenyl-2-(7-methoxy-Δ³-isochromenyl)-1β-methylcyclohexane
CAS No.:81293-75-6
Molecular Formula:C₂₂H₂₈O₄
Molecular Weight:356.462
Hs Code.:

(-)-4α-acetoxy-1-ethenyl-2-(7-methoxy-Δ<sup>3</sup>-isochromenyl)-1β-methylcyclohexane

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Chemical Property of (-)-4α-acetoxy-1-ethenyl-2-(7-methoxy-Δ³-isochromenyl)-1β-methylcyclohexane

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Technology Process of (-)-4α-acetoxy-1-ethenyl-2-(7-methoxy-Δ³-isochromenyl)-1β-methylcyclohexane

There total 19 articles about (-)-4α-acetoxy-1-ethenyl-2-(7-methoxy-Δ³-isochromenyl)-1β-methylcyclohexane 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: 20.0%

: 81277-55-6
4α-acetoxy-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-oxoethyl>-1β-methylcyclohexane

: 77727-36-7
(-)-3α-acetoxy-17-methoxy-D-homo-18-nor-7-oxo-5β-androsta-13,15,17-triene

: 81293-75-6
(-)-4α-acetoxy-1-ethenyl-2-(7-methoxy-Δ³-isochromenyl)-1β-methylcyclohexane

Guidance literature:: In 1,2-dichloro-benzene; for 0.75h; Heating;
DOI:10.1021/jo00133a020

Reference yield:

: 61950-54-7
(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene

: 81293-75-6
(-)-4α-acetoxy-1-ethenyl-2-(7-methoxy-Δ³-isochromenyl)-1β-methylcyclohexane

Guidance literature:: Multi-step reaction with 20 steps

1: 89 percent / H₂ / 10percent palladium on carbon / aq. ethanol / 6 h / 760 Torr / Ambient temperature

2: 79 percent / sodium borohydride / methanol / 1 h / 0 °C

3: 85 percent / pyridine / 16 h / Ambient temperature

4: 96 percent / 5percent aq. hydrochloric acid / acetone / 16 h / Ambient temperature

5: bromine / CHCl₃ / 2 h / 0 °C

6: 97 percent / lithium bromide, lithium carbonate / dimethylformamide / 3.5 h / 125 - 130 °C

7: 1.) sodium amide, 2.) 5percent aq. potassium hydroxide / 1.) ammonia (liquid)/THF, -78 deg C, 2 h, 2.) methanol, room temp., 2 h

8: 90 percent / p-toluenesulfonic acid / benzene / 3 h / Heating

9: 96 percent / sodium / liquid ammonia; tetrahydrofuran; ethanol / 2 h / -78 °C

10: 99 percent / 5percent aq. hydrochloric acid / acetone / 16 h / Ambient temperature

11: pyridinium hydrobromide perbromide / CHCl₃ / 1 h / Ambient temperature

12: 96 percent / lithium bromide, lithium carbonate / dimethylformamide / 14 h / 45 °C

13: 77 percent / 30percent hydrogen peroxide, 10percent aq. sodium hydroxide / methanol / 6 h / Ambient temperature

14: 100 percent / p-toluenesulfonic acid / CH₂Cl₂ / 4 h / Ambient temperature

15: 77 percent / lithium aluminum hydride / tetrahydrofuran / 15 h / Ambient temperature

16: 85 percent / 4-(dimethylamino)pyridine / pyridine / 16 h / Ambient temperature

17: 91 percent / sodium hydride / tetrahydrofuran / 14 h / Heating

18: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

19: 91 percent / pyridine / 14 h / Ambient temperature

20: 20 percent / 1,2-dichloro-benzene / 0.75 h / Heating

With hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; dihydrogen peroxide; bromine; pyridinium hydrobromide perbromide; sodium; lithium carbonate; sodium hydride; toluene-4-sulfonic acid; sodium amide; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; chloroform; ammonia; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; benzene;
DOI:10.1021/jo00133a020

Reference yield:

: 81277-56-7
(+)-(4aR,6R,8aS)-6α-acetoxy-1,2,3,4,4aβ,5,6,7,8,8a-decahydro-1,1-(1,2-ethylenedioxy)-8aβ-methylnaphthalene

: 81293-75-6
(-)-4α-acetoxy-1-ethenyl-2-(7-methoxy-Δ³-isochromenyl)-1β-methylcyclohexane

Guidance literature:: Multi-step reaction with 17 steps

1: 96 percent / 5percent aq. hydrochloric acid / acetone / 16 h / Ambient temperature

2: bromine / CHCl₃ / 2 h / 0 °C

3: 97 percent / lithium bromide, lithium carbonate / dimethylformamide / 3.5 h / 125 - 130 °C

4: 1.) sodium amide, 2.) 5percent aq. potassium hydroxide / 1.) ammonia (liquid)/THF, -78 deg C, 2 h, 2.) methanol, room temp., 2 h

5: 90 percent / p-toluenesulfonic acid / benzene / 3 h / Heating

6: 96 percent / sodium / liquid ammonia; tetrahydrofuran; ethanol / 2 h / -78 °C

7: 99 percent / 5percent aq. hydrochloric acid / acetone / 16 h / Ambient temperature

8: pyridinium hydrobromide perbromide / CHCl₃ / 1 h / Ambient temperature

9: 96 percent / lithium bromide, lithium carbonate / dimethylformamide / 14 h / 45 °C

10: 77 percent / 30percent hydrogen peroxide, 10percent aq. sodium hydroxide / methanol / 6 h / Ambient temperature

11: 100 percent / p-toluenesulfonic acid / CH₂Cl₂ / 4 h / Ambient temperature

12: 77 percent / lithium aluminum hydride / tetrahydrofuran / 15 h / Ambient temperature

13: 85 percent / 4-(dimethylamino)pyridine / pyridine / 16 h / Ambient temperature

14: 91 percent / sodium hydride / tetrahydrofuran / 14 h / Heating

15: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

16: 91 percent / pyridine / 14 h / Ambient temperature

17: 20 percent / 1,2-dichloro-benzene / 0.75 h / Heating

With hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; dihydrogen peroxide; bromine; pyridinium hydrobromide perbromide; sodium; lithium carbonate; sodium hydride; toluene-4-sulfonic acid; sodium amide; lithium bromide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; chloroform; ammonia; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; benzene;
DOI:10.1021/jo00133a020