(4α,7α,9β,13β)-6,6-diethoxy-11,11-diimethyl-2-(methoxycarbonyl)-7-methyl-2-(phenylselenyl)tricyclo<10.2.0.0^9,13>undecan-3-one

Base Information

• Chemical Name: (4α,7α,9β,13β)-6,6-diethoxy-11,11-diimethyl-2-(methoxycarbonyl)-7-methyl-2-(phenylselenyl)tricyclo<10.2.0.0^9,13>undecan-3-one
• CAS No.: 79745-89-4
• Molecular Formula: C₂₆H₃₆O₅Se
• Molecular Weight: 507.529

Synonyms:(4α,7α,9β,13β)-6,6-diethoxy-11,11-diimethyl-2-(methoxycarbonyl)-7-methyl-2-(phenylselenyl)tricyclo<10.2.0.0^9,13>undecan-3-one

Chemical Property of (4α,7α,9β,13β)-6,6-diethoxy-11,11-diimethyl-2-(methoxycarbonyl)-7-methyl-2-(phenylselenyl)tricyclo<10.2.0.0^9,13>undecan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4α,7α,9β,13β)-6,6-diethoxy-11,11-diimethyl-2-(methoxycarbonyl)-7-methyl-2-(phenylselenyl)tricyclo<10.2.0.0^9,13>undecan-3-one

There total 17 articles about (4α,7α,9β,13β)-6,6-diethoxy-11,11-diimethyl-2-(methoxycarbonyl)-7-methyl-2-(phenylselenyl)tricyclo<10.2.0.0^9,13>undecan-3-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:

1-(4,4-dimethyl-1-cyclopenten-1-yl)ethanone (73011-50-4) → (4α,7α,9β,13β)-6,6-diethoxy-11,11-diimethyl-2-(methoxycarbonyl)-7-methyl-2-(phenylselenyl)tricyclo<10.2.0.09,13>undecan-3-one (79745-89-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -78 deg C, 6h, 2.) 25 deg C, 15 min

2: 72 percent / 240 h / 48 °C

3: 96 percent / methanol / 5.4 h / 25 °C / Linde 3-Angstroem molecular sieves

4: 1.) lithium triethylborohydride, 2.) sodium hydride / 1.) THF, 25 deg C, 3 min, 2.) THF, reflux, 5 h

5: 96 percent / lithium aluminium hydride / diethyl ether / 2 h / 0 °C

6: 82 percent / n-butyllithium, tetramethylenediamine / tetrahydrofuran; hexane / 3 h / 25 °C

7: 94 percent / lithium, ethylamine, tert-butyl alcohol / tetrahydrofuran / 1 h / 0 °C

8: 87 percent / chromium trioxide, pyridine / CH₂Cl₂ / 2.5 h / 25 °C

9: 1.) lithium diisopropylamide / 1.) THF, -58 deg C, 50 min, 2.) ether, 5 min

10: 437 mg / lithium diisopropylamine / tetrahydrofuran / 0.17 h

With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; lithium; sodium hydride; lithium triethylborohydride; ethylamine; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ja00367a018

Reference yield:

3,3-diethoxy-2-(ethoxycarbonyl)cyclobutene (76221-41-5) → (4α,7α,9β,13β)-6,6-diethoxy-11,11-diimethyl-2-(methoxycarbonyl)-7-methyl-2-(phenylselenyl)tricyclo<10.2.0.09,13>undecan-3-one (79745-89-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 72 percent / 240 h / 48 - 50 °C

2: 97 percent / lithium aluminium hydride / diethyl ether / 0.5 h / 0 °C

3: 86 percent / sodium hydride, tetramethylethylenediamine / 1,2-dimethoxy-ethane / 20 h / 55 °C

4: 90 percent / lithium, ethylamine / 2 h / -78 °C

5: 56 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 0.33 h / 0 °C

6: 1.) lithium diisopropylamide / 1.) THF, -58 deg C, 50 min, 2.) ether, 5 min

7: 437 mg / lithium diisopropylamine / tetrahydrofuran / 0.17 h

With lithium aluminium tetrahydride; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; lithium; sodium hydride; ethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether;

DOI:10.1021/ja00367a018

Reference yield:

1,4,4-trimethyl-1-cyclohexene (3419-71-4) → (4α,7α,9β,13β)-6,6-diethoxy-11,11-diimethyl-2-(methoxycarbonyl)-7-methyl-2-(phenylselenyl)tricyclo<10.2.0.09,13>undecan-3-one (79745-89-4)

Guidance literature:

Multi-step reaction with 11 steps

2: 99 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -78 deg C, 6h, 2.) 25 deg C, 15 min

3: 72 percent / 240 h / 48 °C

4: 96 percent / methanol / 5.4 h / 25 °C / Linde 3-Angstroem molecular sieves

5: 1.) lithium triethylborohydride, 2.) sodium hydride / 1.) THF, 25 deg C, 3 min, 2.) THF, reflux, 5 h

6: 96 percent / lithium aluminium hydride / diethyl ether / 2 h / 0 °C

7: 82 percent / n-butyllithium, tetramethylenediamine / tetrahydrofuran; hexane / 3 h / 25 °C

8: 94 percent / lithium, ethylamine, tert-butyl alcohol / tetrahydrofuran / 1 h / 0 °C

9: 87 percent / chromium trioxide, pyridine / CH₂Cl₂ / 2.5 h / 25 °C

10: 1.) lithium diisopropylamide / 1.) THF, -58 deg C, 50 min, 2.) ether, 5 min

11: 437 mg / lithium diisopropylamine / tetrahydrofuran / 0.17 h

With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; lithium; sodium hydride; lithium triethylborohydride; ethylamine; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ja00367a018

upstream raw materials:

Phenylselenyl chloride

(4α,7α,9β,13β)-6,6-diethoxy-2-(methoxycarbonyl)-7,11,11-trimethyltricyclo<10.2.0.0^9,13>undecan-3-one

1,4,4-trimethyl-1-cyclohexene

1-(4,4-dimethyl-1-cyclopenten-1-yl)ethanone

Downstream raw materials:

(+/-)-illudol

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