(1α,3aβ,6aβ)-hexahydro-1,3a,6a-trimethyl-1-<3-oxo-4-(phenylthio)butyl>-2(1H)-pentalenon

Base Information

Chemical Name:(1α,3aβ,6aβ)-hexahydro-1,3a,6a-trimethyl-1-<3-oxo-4-(phenylthio)butyl>-2(1H)-pentalenon
CAS No.:80907-01-3
Molecular Formula:C₂₁H₂₈O₂S
Molecular Weight:344.518
Hs Code.:

Synonyms:(1α,3aβ,6aβ)-hexahydro-1,3a,6a-trimethyl-1-<3-oxo-4-(phenylthio)butyl>-2(1H)-pentalenon

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Chemical Property of (1α,3aβ,6aβ)-hexahydro-1,3a,6a-trimethyl-1-<3-oxo-4-(phenylthio)butyl>-2(1H)-pentalenon

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Technology Process of (1α,3aβ,6aβ)-hexahydro-1,3a,6a-trimethyl-1-<3-oxo-4-(phenylthio)butyl>-2(1H)-pentalenon

There total 16 articles about (1α,3aβ,6aβ)-hexahydro-1,3a,6a-trimethyl-1-<3-oxo-4-(phenylthio)butyl>-2(1H)-pentalenon 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: 55.0%

: 13307-75-0
(phenylthio)methyllithium

: 72346-57-7
(3aα,4α,8α,8aα)-octahydro-3a,8,8a-trimethyl-4,8-methanoazulene-5,9(1H)-dione

: 80907-01-3
(1α,3aβ,6aβ)-hexahydro-1,3a,6a-trimethyl-1-<3-oxo-4-(phenylthio)butyl>-2(1H)-pentalenon

Guidance literature:: In tetrahydrofuran; at -78 - -30 ℃; for 2h;
DOI:10.1021/ja00372a016

Reference yield:

: 74629-83-7,74629-84-8,80906-77-0,80906-78-1
(3aR,6aR)-1-Allyl-1,3a,6a-trimethyl-octahydro-pentalen-2-ol

: 80907-01-3
(1α,3aβ,6aβ)-hexahydro-1,3a,6a-trimethyl-1-<3-oxo-4-(phenylthio)butyl>-2(1H)-pentalenon

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) KH / tetrahydrofuran / 18 h / Heating

2: 1.) B₂H₆, 2.) NaOH-H₂O₂ / 1.) THF, RT, 18 h, 2.) THF-H₂O, 0,5 h

3: CrO₃-dipyridine complex / CH₂Cl₂ / 0.5 h / Ambient temperature

4: p-toluenesulfonic acid hydrate / benzene / 18 h / Heating

5: 62 percent / Li / liquid ammonia; tetrahydrofuran / -33 °C

6: 77 percent / CrO₃-dipyridine complex / CH₂Cl₂

7: 100 percent / 1.2 N hydrochloric acid / acetone / 3 h / Heating

8: 92 percent / 6 N chromic acid / acetone / 0.17 h / Ambient temperature

9: 64 percent / Ac₂O, HClO₄ / CH₂Cl₂ / 0.33 h

10: 90 percent / i-Bu₂AlH / tetrahydrofuran / 1.) -78 deg C, 5 min, 2.) 0 deg C, 6 h

11: 62 percent / 6 N chromic acid / acetone / 0.17 h

12: 55 percent / tetrahydrofuran / 2 h / -78 - -30 °C

With hydrogenchloride; sodium hydroxide; perchloric acid; dihydrogen peroxide; acetic anhydride; chromic acid; lithium; potassium hydride; dipyridine chromium trioxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; diborane; In tetrahydrofuran; dichloromethane; ammonia; acetone; benzene;
DOI:10.1021/ja00372a016

Reference yield:

: 80906-89-4,80906-90-7
3-((3aR,6aR)-2-Benzyloxy-1,3a,6a-trimethyl-octahydro-pentalen-1-yl)-propionaldehyde

: 80907-01-3
(1α,3aβ,6aβ)-hexahydro-1,3a,6a-trimethyl-1-<3-oxo-4-(phenylthio)butyl>-2(1H)-pentalenon

Guidance literature:: Multi-step reaction with 9 steps

1: p-toluenesulfonic acid hydrate / benzene / 18 h / Heating

2: 62 percent / Li / liquid ammonia; tetrahydrofuran / -33 °C

3: 77 percent / CrO₃-dipyridine complex / CH₂Cl₂

4: 100 percent / 1.2 N hydrochloric acid / acetone / 3 h / Heating

5: 92 percent / 6 N chromic acid / acetone / 0.17 h / Ambient temperature

6: 64 percent / Ac₂O, HClO₄ / CH₂Cl₂ / 0.33 h

7: 90 percent / i-Bu₂AlH / tetrahydrofuran / 1.) -78 deg C, 5 min, 2.) 0 deg C, 6 h

8: 62 percent / 6 N chromic acid / acetone / 0.17 h

9: 55 percent / tetrahydrofuran / 2 h / -78 - -30 °C

With hydrogenchloride; perchloric acid; acetic anhydride; chromic acid; lithium; dipyridine chromium trioxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; ammonia; acetone; benzene;
DOI:10.1021/ja00372a016