trans-12α-benzoyloxy-8β-hydroxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-diene-4-one

Base Information

• Chemical Name: trans-12α-benzoyloxy-8β-hydroxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-diene-4-one
• CAS No.: 111251-76-4
• Molecular Formula: C₂₃H₂₆O₄
• Molecular Weight: 366.457

Synonyms:trans-12α-benzoyloxy-8β-hydroxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-diene-4-one

Chemical Property of trans-12α-benzoyloxy-8β-hydroxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-diene-4-one

Chemical Property:

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Technology Process of trans-12α-benzoyloxy-8β-hydroxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-diene-4-one

There total 12 articles about trans-12α-benzoyloxy-8β-hydroxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-diene-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: 94.0%

benzoyl chloride (98-88-4) + trans-8β,12α-dihydroxy-6β,9α,10-trimethyltricyclo<7.4.0.02,6>trideca-2,10-diene-4-one (111251-74-2,111251-75-3) → trans-12α-benzoyloxy-8β-hydroxy-6β,9α,10-trimethyltricyclo<7.4.0.02,6>trideca-2,10-diene-4-one (111251-76-4)

Guidance literature:

With triethylamine; In dichloromethane; at 3 ℃; for 16h;

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) → Benzoic acid (3aS,5R,5aR,8R,9aS)-5-hydroxy-3a,5a,6-trimethyl-2-oxo-3,3a,4,5,5a,8,9,9a-octahydro-2H-cyclopenta[a]naphthalen-8-yl ester (111251-76-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2: NaBH₄ / methanol

3: MnO₂

4: Raney-nickel

With manganese(IV) oxide; sodium tetrahydroborate; nickel; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;

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-8β-hydroxy-6β,9α,10-trimethyltricyclo<7.4.0.02,6>trideca-2,10-diene-4-one (111251-76-4)

Guidance literature:

Multi-step reaction with 7 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

With manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; W₂ Raney-nickel; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

benzoyl chloride

trans-8β,12α-dihydroxy-6β,9α,10-trimethyltricyclo<7.4.0.0^2,6>trideca-2,10-diene-4-one

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:

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

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

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