acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester

Base Information

Chemical Name:acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester
CAS No.:922174-29-6
Molecular Formula:C₂₄H₃₁NO₂
Molecular Weight:365.516
Hs Code.:

Synonyms:acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester

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Chemical Property of acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester

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Technology Process of acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester

There total 11 articles about acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester 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: 53.0%

: 922174-28-5
acetic acid 3,5,5-trimethyl-4-[3-(4-oxo-cyclohept-2-enylidene)-but-1-enyl]-cyclohex-3-enyl ester

: 2537-48-6
diethyl 1-cyanomethylphosphonate

: acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester

: 922174-29-6
acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester

Guidance literature:: diethyl 1-cyanomethylphosphonate; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

acetic acid 3,5,5-trimethyl-4-[3-(4-oxo-cyclohept-2-enylidene)-but-1-enyl]-cyclohex-3-enyl ester; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1139/V06-092

Reference yield:

: 922174-24-1
acetic acid 4-hydroxymethyl-3,5,5-trimethyl-cyclohex-3-enyl ester

: 922174-29-6
acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 94 percent / triphenylphosphine; carbon tetrabromide / 1 h / 20 °C

2.1: 1.37 g / benzene / 12 h / Heating

3.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

3.2: 40 percent / tetrahydrofuran; hexane / 14 h / 20 °C

4.1: 63 percent / 4-(dimethylamino)pyridine; pyridine / 12 h / 20 °C

5.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

6.1: 84 percent / MnO₂ / CH₂Cl₂ / 0 - 20 °C

7.1: NaH / tetrahydrofuran / 0 - 20 °C

7.2: 27 percent / tetrahydrofuran / 12 h / 20 °C

With pyridine; dmap; manganese(IV) oxide; n-butyllithium; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; benzene; 3.2: Wittig reaction / 7.2: Horner-Emmons-Wadsworth reaction;
DOI:10.1139/V06-092

Reference yield:

: 922174-25-2
acetic acid 4-bromomethyl-3,5,5-trimethyl-cyclohex-3-enyl ester

: 922174-29-6
acetic acid 4-[3-(4-cyanomethylene-cyclohept-2-enylidene)-but-1-enyl]-3,5,5-trimethyl-cyclohex-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1.37 g / benzene / 12 h / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

2.2: 40 percent / tetrahydrofuran; hexane / 14 h / 20 °C

3.1: 63 percent / 4-(dimethylamino)pyridine; pyridine / 12 h / 20 °C

4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

5.1: 84 percent / MnO₂ / CH₂Cl₂ / 0 - 20 °C

6.1: NaH / tetrahydrofuran / 0 - 20 °C

6.2: 27 percent / tetrahydrofuran / 12 h / 20 °C

With pyridine; dmap; manganese(IV) oxide; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; hexane; dichloromethane; benzene; 2.2: Wittig reaction / 6.2: Horner-Emmons-Wadsworth reaction;
DOI:10.1139/V06-092