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

Base Information

• Chemical Name: trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-triene-4-one
• CAS No.: 111251-78-6
• Molecular Formula: C₂₃H₂₆O₃
• Molecular Weight: 350.458

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

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

Chemical Property:

Purity/Quality:

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

There total 11 articles about trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-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: 92.0%

trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.02,6>trideca-2,7,10-triene-4-one (111251-77-5) → trans-12α-benzoyloxy-6β,9α,10-trimethyltricyclo<7.4.0.02,6>trideca-2,10-triene-4-one (111251-78-6)

Guidance literature:

With hydrogen; Wilkinson's catalyst; In benzene; for 48h; under 2585.7 Torr;

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-2,10-triene-4-one (111251-78-6)

Guidance literature:

Multi-step reaction with 10 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

10: 92 percent / hydrogen / (Ph₃P)3RhCl / benzene / 48 h / 2585.7 Torr

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

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-2,10-triene-4-one (111251-78-6)

Guidance literature:

Multi-step reaction with 9 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

9: 92 percent / hydrogen / (Ph₃P)3RhCl / benzene / 48 h / 2585.7 Torr

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

upstream raw materials:

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

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

Downstream raw materials:

Benzoic acid (R)-2-((4R,5R,7aS)-5-acetyl-5,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-1-formyl-ethyl ester

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