(1R,7S,8S)-3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2⁽⁶⁾-en-7-yl 4-nitrobenzoate

Base Information

• Chemical Name: (1R,7S,8S)-3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2⁽⁶⁾-en-7-yl 4-nitrobenzoate
• CAS No.: 581097-03-2
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.444

Synonyms:(1R,7S,8S)-3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2⁽⁶⁾-en-7-yl 4-nitrobenzoate

Chemical Property of (1R,7S,8S)-3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2⁽⁶⁾-en-7-yl 4-nitrobenzoate

Chemical Property:

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Technology Process of (1R,7S,8S)-3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2⁽⁶⁾-en-7-yl 4-nitrobenzoate

There total 16 articles about (1R,7S,8S)-3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2⁽⁶⁾-en-7-yl 4-nitrobenzoate 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: 85.0%

(1R,7R,8S)-7-hydroxy-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2(6)-ene-3-one (581097-01-0) + 4-nitro-benzoic acid (62-23-7) → (1R,7S,8S)-3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2(6)-en-7-yl 4-nitrobenzoate (581097-03-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1021/ol034635p

Reference yield:

(1R,8S)-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2(6)-ene-3,7-dione (581096-99-3) → (1R,7S,8S)-3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2(6)-en-7-yl 4-nitrobenzoate (581097-03-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1 h / 0 °C

2: 85 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 8 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 2: Mitsunobu inversion;

DOI:10.1021/ol034635p

Reference yield:

(-)-(1R,5S)-1,5-dimethylbicyclo[3.3.0]octane-2,7-dione (137740-19-3) → (1R,7S,8S)-3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2(6)-en-7-yl 4-nitrobenzoate (581097-03-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: boron trifluoride diethyl etherate / benzene / 0.67 h / 0 - 5 °C

2.1: ethanol / 0.5 h / Reflux

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 °C / Inert atmosphere

3.2: 6 h / 20 °C / Inert atmosphere

4.1: pyridine; trichlorophosphate / 1 h / Cooling with ice

5.1: methanol; pyridinium p-toluenesulfonate / 6 h / 20 °C

6.1: methanesulfonic acid / dichloromethane / 0.5 h / 20 °C

7.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h

7.2: 17 h / 20 °C

8.1: di-tert-butyl chromate / tetrachloromethane / 9 h / 80 °C

9.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 - 20 °C

10.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 8 h / 20 °C

With pyridine; methanol; sodium tetrahydroborate; n-butyllithium; methanesulfonic acid; ethanol; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; di-tert-butyl chromate; pyridinium p-toluenesulfonate; sodium hydride; triphenylphosphine; trichlorophosphate; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; mineral oil; benzene; 9.1: Luche reduction / 10.1: Mitsunobu reaction;

upstream raw materials:

(1R,7R,8S)-7-hydroxy-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2⁽⁶⁾-ene-3-one

4-nitro-benzoic acid

(1R,8S)-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2⁽⁶⁾-ene-3,7-dione

(1R,2R,5R)-1,5-dimethyl-2-[3-(tetrahydro-2-pyranyloxy)-1-propynyl]bicyclo[3.3.0]octan-2-ol

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