trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,7,10-triene-4-one

Base Information

• Chemical Name: trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,7,10-triene-4-one
• CAS No.: 111251-77-5
• Molecular Formula: C₂₃H₂₄O₃
• Molecular Weight: 348.442

Synonyms:trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,7,10-triene-4-one

Chemical Property of trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,7,10-triene-4-one

Chemical Property:

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Technology Process of trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,7,10-triene-4-one

There total 10 articles about trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,7,10-triene-4-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:

cis-12β-hydroxy-6β,9α,10-trimethyl-3-(phenylthio)tricyclo<7.4..0.02,6>trideca-2,10-diene-4,8-dione (80114-30-3,111251-70-8) → trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.02,6>trideca-2,7,10-triene-4-one (111251-77-5)

Guidance literature:

Multi-step reaction with 9 steps

1: Ph₃P, DEAD / tetrahydrofuran / 1 h / 15 - 20 °C

2: NaBH₄ / methanol

3: MnO₂

4: 1M aq. NaOH / methanol / 50 °C

5: W₂ Raney-nickel / methanol / 2 h / Ambient temperature

6: NaOH / methanol / Heating; t 1/2 = ca. 24 h

7: 94 percent / Et₃N / CH₂Cl₂; various solvent(s) / 16 h / 3 °C

8: pyridine / 15 h / 50 °C

9: DBU / toluene / 72 h / Heating

With pyridine; manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; W₂ Raney-nickel; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene;

Reference yield:

cis-12α-benzoyloxy-6β,9α,10-trimethyl-3-(phenylthio)tricyclo<7.4.0.02,6>trideca-2,10-diene-4,8-dione (111251-71-9) → trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.02,6>trideca-2,7,10-triene-4-one (111251-77-5)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH₄ / methanol

2: MnO₂

3: 1M aq. NaOH / methanol / 50 °C

4: W₂ Raney-nickel / methanol / 2 h / Ambient temperature

5: NaOH / methanol / Heating; t 1/2 = ca. 24 h

6: 94 percent / Et₃N / CH₂Cl₂; various solvent(s) / 16 h / 3 °C

7: pyridine / 15 h / 50 °C

8: DBU / toluene / 72 h / Heating

With pyridine; manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; W₂ Raney-nickel; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; toluene;

Reference yield:

Benzoic acid (3aS,5R,5aR,8R,9aR)-5-methanesulfonyloxy-3a,5a,6-trimethyl-2-oxo-3,3a,4,5,5a,8,9,9a-octahydro-2H-cyclopenta[a]naphthalen-8-yl ester → trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.02,6>trideca-2,7,10-triene-4-one (111251-77-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 72h; Yield given; Heating;

upstream raw materials:

benzoyl chloride

cis-12β-hydroxy-6β,9α,10-trimethyl-3-(phenylthio)tricyclo<7.4..0.0^2,6>trideca-2,10-diene-4,8-dione

cis-8β,12α-dihydroxy-6β,9α,10-trimethyl-3-(phenylthio)tricyclo<7.4.0.0^2,6>trideca-2,10-diene-4-one

cis-12α-benzoyloxy-8β-hydroxy-6β,9α,10-trimethyl-3-(phenylthio)tricyclo<7.4.0.0^2,6>trideca-2,10-diene-4-one

Downstream raw materials:

trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-triene-4-one

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