((1R,3aR,6aR)-1-Allyl-2,2-dimethyl-4-methylene-5-oxo-hexahydro-pentalen-3a-yl)-acetaldehyde

Base Information

Chemical Name:((1R,3aR,6aR)-1-Allyl-2,2-dimethyl-4-methylene-5-oxo-hexahydro-pentalen-3a-yl)-acetaldehyde
CAS No.:83588-31-2
Molecular Formula:C₁₆H₂₂O₂
Molecular Weight:246.349
Hs Code.:

Synonyms:((1R,3aR,6aR)-1-Allyl-2,2-dimethyl-4-methylene-5-oxo-hexahydro-pentalen-3a-yl)-acetaldehyde

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Chemical Property of ((1R,3aR,6aR)-1-Allyl-2,2-dimethyl-4-methylene-5-oxo-hexahydro-pentalen-3a-yl)-acetaldehyde

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Technology Process of ((1R,3aR,6aR)-1-Allyl-2,2-dimethyl-4-methylene-5-oxo-hexahydro-pentalen-3a-yl)-acetaldehyde

There total 1 articles about ((1R,3aR,6aR)-1-Allyl-2,2-dimethyl-4-methylene-5-oxo-hexahydro-pentalen-3a-yl)-acetaldehyde 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:

: 22748-16-9
4,4-dimethylcyclopent-2-ene-1-one

: 83588-31-2
((1R,3aR,6aR)-1-Allyl-2,2-dimethyl-4-methylene-5-oxo-hexahydro-pentalen-3a-yl)-acetaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) Rieke magnesium, cuprous bromide-dimethyl sulfide, 2.) Et₃N / 1.) THF, ether, -78 deg C, 2.) -78 deg C -> 5 deg C

2: 1.) LiNH₂, 2.) perchloric acid / 1.) liquid ammonia, THF, -33 deg C, 6 min 2.) CCl₂H₂, 2 h

3: 75 percent / sodium ethoxide / ethanol / 2 h / Ambient temperature

4: 99 percent / p-TsOH / benzene / 4 h / Heating

5: 68 percent / diisobutylaluminum hydride / diethyl ether; hexane / -116 deg C, 2 h -> -50 deg C

6: 90 percent / mercuric acetate / 6 h / Heating

7: 56 percent / decahydronaphthalene / 4 h / 155 °C

8: 91 percent / pyridinium tosylate / acetone / 0.25 h / Heating

With perchloric acid; lithium amide; copper(I) bromide dimethylsulfide complex; mercury(II) diacetate; sodium ethanolate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; triethylamine; In diethyl ether; ethanol; hexane; acetone; decalin; benzene;
DOI:10.1021/ja00388a029

Reference yield:

: 83588-31-2
((1R,3aR,6aR)-1-Allyl-2,2-dimethyl-4-methylene-5-oxo-hexahydro-pentalen-3a-yl)-acetaldehyde

: 83588-36-7
5-(benzyloxy)octahydro-7-(2-iodoethyl)-8,8-dimethylpentaleno<1,6a-c>pyran-2(1H)-one

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaOH, 2.) Jones reagent / 1.) THF, water, 1 h, 2.) acetone, 0 deg C, 30 min

2: 1.) tert-butylamine-borane, 2.) HCl, 3.) collidine, trifluoromethanesulfonic anhydride

3: 1.) ozone, 2.) dimethyl sulfide / 1.) methanol, -78 deg C, 5 min, 2.) -12 deg C

4: 1.) tert-butylamine-borane, 2.) HCl / 1.) THF, 0 deg C, 30 min

5: 83 percent / 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0 °C

6: 77 percent / NaI / acetone / 1 h

With 2,3,5-trimethyl-pyridine; hydrogenchloride; dmap; sodium hydroxide; jones reagent; dimethylsulfide; borane tert-butylamine; ozone; trifluoromethanesulfonic acid anhydride; triethylamine; sodium iodide; In dichloromethane; acetone;
DOI:10.1021/ja00388a029

Reference yield:

: 83588-31-2
((1R,3aR,6aR)-1-Allyl-2,2-dimethyl-4-methylene-5-oxo-hexahydro-pentalen-3a-yl)-acetaldehyde

: 83588-40-3
Toluene-4-sulfonic acid 2-((4aS,6aR,7R,9aR)-8,8-dimethyl-2,5-dioxo-decahydro-pentaleno[1,6a-c]pyran-7-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaOH, 2.) Jones reagent / 1.) THF, water, 1 h, 2.) acetone, 0 deg C, 30 min

2: 1.) ozone, 2.) dimethyl sulfide / 1.) methanol, -78 deg C, 20 min, 2.) 0 deg C

3: 1.) tert-butylamine-borane, 2.) H₂SO₄ / 1.) THF, 15 min

4: 73 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With sodium hydroxide; jones reagent; dimethylsulfide; sulfuric acid; borane tert-butylamine; ozone; triethylamine; In dichloromethane;
DOI:10.1021/ja00388a029