methyl 4-{N-benzyl-[2-(phenylselanyl)-2-oxoethyl]amino}cyclohex-1-enecarboxylate

Base Information

Chemical Name:methyl 4-{N-benzyl-[2-(phenylselanyl)-2-oxoethyl]amino}cyclohex-1-enecarboxylate
CAS No.:422506-97-6
Molecular Formula:C₂₃H₂₅NO₃Se
Molecular Weight:442.416
Hs Code.:

Synonyms:methyl 4-{N-benzyl-[2-(phenylselanyl)-2-oxoethyl]amino}cyclohex-1-enecarboxylate

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Chemical Property of methyl 4-{N-benzyl-[2-(phenylselanyl)-2-oxoethyl]amino}cyclohex-1-enecarboxylate

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Technology Process of methyl 4-{N-benzyl-[2-(phenylselanyl)-2-oxoethyl]amino}cyclohex-1-enecarboxylate

There total 7 articles about methyl 4-{N-benzyl-[2-(phenylselanyl)-2-oxoethyl]amino}cyclohex-1-enecarboxylate 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: 70.0%

: 5707-04-0
Phenylselenyl chloride

: N-benzyl-N-carboxymethyl-N-(4-methoxycarbonylcyclohex-3-en-1-yl)ammonium trifluoroacetate

: 422506-97-6
methyl 4-{N-benzyl-[2-(phenylselanyl)-2-oxoethyl]amino}cyclohex-1-enecarboxylate

Guidance literature:: N-benzyl-N-carboxymethyl-N-(4-methoxycarbonylcyclohex-3-en-1-yl)ammonium trifluoroacetate; With triethylamine; In dichloromethane; for 0.5h;

Phenylselenyl chloride; With tributylphosphine; In tetrahydrofuran; dichloromethane; at 20 ℃; for 24h; Further stages.;
DOI:10.1021/jo0163849

Reference yield:

: benzyl-(4-hydrazono-cyclohexyl)-carbamic acid tert-butyl ester

: 422506-97-6
methyl 4-{N-benzyl-[2-(phenylselanyl)-2-oxoethyl]amino}cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 885 mg / I₂; 2-tetr-butyl-1,1,3,3-tetramethylguanidine / diethyl ether / 0 - 90 °C

2.1: 75 percent / PPh₃; DMPU; Et₃N / Pd(OAc)2 / 24 h / 55 °C

3.1: TFA / CH₂Cl₂ / 45 h / 20 °C

4.1: 85 percent / Na₂CO₃ / acetonitrile / 24 h / Heating

5.1: 91 percent / CH₂Cl₂ / 0.75 h / 20 °C

6.1: Et₃N / CH₂Cl₂ / 0.5 h

6.2: 70 percent / PBu₃ / CH₂Cl₂; tetrahydrofuran / 24 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine; sodium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium diacetate; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo0163849

Reference yield:

: 188562-91-6
tert-butyl N-benzyl(4-oxocyclohexyl)carbamate

: 422506-97-6
methyl 4-{N-benzyl-[2-(phenylselanyl)-2-oxoethyl]amino}cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: hydrazine monohydrate; Et₃N / ethanol / 1.5 h / Heating

2.1: 885 mg / I₂; 2-tetr-butyl-1,1,3,3-tetramethylguanidine / diethyl ether / 0 - 90 °C

3.1: 75 percent / PPh₃; DMPU; Et₃N / Pd(OAc)2 / 24 h / 55 °C

4.1: TFA / CH₂Cl₂ / 45 h / 20 °C

5.1: 85 percent / Na₂CO₃ / acetonitrile / 24 h / Heating

6.1: 91 percent / CH₂Cl₂ / 0.75 h / 20 °C

7.1: Et₃N / CH₂Cl₂ / 0.5 h

7.2: 70 percent / PBu₃ / CH₂Cl₂; tetrahydrofuran / 24 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine; sodium carbonate; hydrazine hydrate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium diacetate; In diethyl ether; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jo0163849