2-diazo-3-[3-ethyl-3-[(Z)-4-(2-nitrophenyl)-but-3-en-yl]-2-thioxopiperidin-1-yl]-3-oxopropionic acid ethyl ester

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Chemical Name:2-diazo-3-[3-ethyl-3-[(Z)-4-(2-nitrophenyl)-but-3-en-yl]-2-thioxopiperidin-1-yl]-3-oxopropionic acid ethyl ester
CAS No.:861219-74-1
Molecular Formula:C₂₂H₂₆N₄O₅S
Molecular Weight:458.538
Hs Code.:

Synonyms:2-diazo-3-[3-ethyl-3-[(Z)-4-(2-nitrophenyl)-but-3-en-yl]-2-thioxopiperidin-1-yl]-3-oxopropionic acid ethyl ester

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Chemical Property of 2-diazo-3-[3-ethyl-3-[(Z)-4-(2-nitrophenyl)-but-3-en-yl]-2-thioxopiperidin-1-yl]-3-oxopropionic acid ethyl ester

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Technology Process of 2-diazo-3-[3-ethyl-3-[(Z)-4-(2-nitrophenyl)-but-3-en-yl]-2-thioxopiperidin-1-yl]-3-oxopropionic acid ethyl ester

There total 8 articles about 2-diazo-3-[3-ethyl-3-[(Z)-4-(2-nitrophenyl)-but-3-en-yl]-2-thioxopiperidin-1-yl]-3-oxopropionic acid ethyl 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: 72.0%

: 861219-71-8
3-ethyl-3-[(Z)-4-(2-nitrophenyl)but-3-enyl]piperidine-2-thione

: 57072-87-4
chlorocarbonyl-diazo-acetic acid ethyl ester

: 861219-74-1
2-diazo-3-[3-ethyl-3-[(Z)-4-(2-nitrophenyl)-but-3-en-yl]-2-thioxopiperidin-1-yl]-3-oxopropionic acid ethyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 0.166667h;
DOI:10.1021/ol0508779

Reference yield:

: 675-20-7
piperidin-2-one

: 861219-74-1
2-diazo-3-[3-ethyl-3-[(Z)-4-(2-nitrophenyl)-but-3-en-yl]-2-thioxopiperidin-1-yl]-3-oxopropionic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

2.2: 4.6 g / tetrahydrofuran; hexane / -78 - 20 °C

3.1: Br₂ / CCl₄ / 1 h / 25 °C

4.1: 3.0 g / LDA / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 85 percent / CuI; iPr₂NH / (Ph₃P)2PdCl₂ / tetrahydrofuran / 12 h / 20 °C

6.1: 83 percent / tri-o-tolylphosphine; AcOH; 1,1,3,3-tetramethyldisiloxane / Pd₂(dba)3 / benzene / 1 h / 25 °C

7.1: 87 percent / Lawesson's reagent / toluene / 1 h / Heating

8.1: 72 percent / Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

With Lawessons reagent; copper(l) iodide; n-butyllithium; 1,1,3,3-Tetramethyldisiloxane; bromine; acetic acid; triethylamine; diisopropylamine; tris-(o-tolyl)phosphine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; toluene; benzene;
DOI:10.1021/ol0508779

Reference yield:

: 155193-60-5
3-(Buten-4-yl)-2(1H)-piperidinone

: 861219-74-1
2-diazo-3-[3-ethyl-3-[(Z)-4-(2-nitrophenyl)-but-3-en-yl]-2-thioxopiperidin-1-yl]-3-oxopropionic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

1.2: 4.6 g / tetrahydrofuran; hexane / -78 - 20 °C

2.1: Br₂ / CCl₄ / 1 h / 25 °C

3.1: 3.0 g / LDA / tetrahydrofuran; hexane / -78 - 20 °C

4.1: 85 percent / CuI; iPr₂NH / (Ph₃P)2PdCl₂ / tetrahydrofuran / 12 h / 20 °C

5.1: 83 percent / tri-o-tolylphosphine; AcOH; 1,1,3,3-tetramethyldisiloxane / Pd₂(dba)3 / benzene / 1 h / 25 °C

6.1: 87 percent / Lawesson's reagent / toluene / 1 h / Heating

7.1: 72 percent / Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

With Lawessons reagent; copper(l) iodide; n-butyllithium; 1,1,3,3-Tetramethyldisiloxane; bromine; acetic acid; triethylamine; diisopropylamine; tris-(o-tolyl)phosphine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; toluene; benzene;
DOI:10.1021/ol0508779