dimethyl 2-(2-nitro-2-phenylselenylethyl)-2-((2E)-2,4-pentadienyl)propanedioate

Base Information

Chemical Name:dimethyl 2-(2-nitro-2-phenylselenylethyl)-2-((2E)-2,4-pentadienyl)propanedioate
CAS No.:953089-36-6
Molecular Formula:C₁₈H₂₁NO₆Se
Molecular Weight:426.328
Hs Code.:

Synonyms:dimethyl 2-(2-nitro-2-phenylselenylethyl)-2-((2E)-2,4-pentadienyl)propanedioate

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Chemical Property of dimethyl 2-(2-nitro-2-phenylselenylethyl)-2-((2E)-2,4-pentadienyl)propanedioate

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Technology Process of dimethyl 2-(2-nitro-2-phenylselenylethyl)-2-((2E)-2,4-pentadienyl)propanedioate

There total 1 articles about dimethyl 2-(2-nitro-2-phenylselenylethyl)-2-((2E)-2,4-pentadienyl)propanedioate 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: 77.0%

: 3638-64-0,26618-70-2
1-nitroethylene

: 34837-55-3
Phenylselenyl bromide

: 75283-58-8
2-(2,4-pentadienyl)malonic acid dimethyl ester

: 953089-36-6
dimethyl 2-(2-nitro-2-phenylselenylethyl)-2-((2E)-2,4-pentadienyl)propanedioate

Guidance literature:: 2-(2,4-pentadienyl)malonic acid dimethyl ester; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃;

1-nitroethylene; In tetrahydrofuran; at -76 - -75 ℃; for 1h;

Phenylselenyl bromide; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1002/adsc.200600301

Reference yield:

: 953089-36-6
dimethyl 2-(2-nitro-2-phenylselenylethyl)-2-((2E)-2,4-pentadienyl)propanedioate

: 11-benzyl-8-(tert-butyl-dimethyl-silanyloxy)-11b-[2-(tert-butyl-dimethyl-silanyloxy)-vinyl]-5-methyl-6-oxo-5,6,7,7a,8,9,10,11,11a,11b-decahydro-5,11-diaza-benzo[c]fluorene-6a-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 95 percent / m-CPBA / tetrahydrofuran / -77 - 20 °C

2.1: LDA; diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.33 h / -75 °C

2.2: tetrahydrofuran; hexane / 0.5 h / -75 °C

2.3: 98 percent / tetrahydrofuran; hexane / -75 - 20 °C

3.1: (siamyl)2BH / tetrahydrofuran / 2 h / 22 °C

3.2: 75 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 22 °C

4.1: 96 percent / pyridine / 0.17 h / 0 °C

5.1: 67 percent / Raney nickel; H₂ / methanol / 36 h / 22 °C / 18617.3 Torr

6.1: 78 percent / K₂CO₃ / dimethylformamide / 2.5 h

7.1: 84 percent / imidazole / dimethylformamide / 12 h / 22 °C

8.1: LDA / tetrahydrofuran; hexane / -107 - 22 °C

9.1: 52 percent / tetrahydrofuran / -106 - 22 °C

10.1: 86 percent / m-CPBA; diisopropylamine / CH₂Cl₂ / -77 - 22 °C

11.1: 85 percent / EtMgCl / tetrahydrofuran; diethyl ether; methanol / 0.83 h / -15 °C

12.1: 87 percent / NaH / dimethylformamide / 0 - 22 °C

13.1: Et₃N; trimethylsilyl triflate / CH₂Cl₂ / 0 - 22 °C

14.1: 0.561 g / BH₃*THF / tetrahydrofuran / 13.5 h / 22 °C

15.1: 50 percent / imidazole

16.1: PPh₃; Et₃N / Pd(OAc)2 / acetonitrile / 100 °C

With 1H-imidazole; n-butyllithium; borane-THF; trimethylsilyl trifluoromethanesulfonate; hydrogen; ethylmagnesium chloride; bis-(1,2-dimethylpropyl)borane; nickel; sodium hydride; potassium carbonate; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diisopropyl amide; palladium diacetate; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.2: Michael addition / 16.1: Heck reaction;
DOI:10.1002/adsc.200600301

Reference yield:

: 953089-36-6
dimethyl 2-(2-nitro-2-phenylselenylethyl)-2-((2E)-2,4-pentadienyl)propanedioate

: C₃₈H₅₆N₂O₄Si₂

Guidance literature:: Multi-step reaction with 16 steps

1.1: 95 percent / m-CPBA / tetrahydrofuran / -77 - 20 °C

2.1: LDA; diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.33 h / -75 °C

2.2: tetrahydrofuran; hexane / 0.5 h / -75 °C

2.3: 98 percent / tetrahydrofuran; hexane / -75 - 20 °C

3.1: (siamyl)2BH / tetrahydrofuran / 2 h / 22 °C

3.2: 75 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 22 °C

4.1: 96 percent / pyridine / 0.17 h / 0 °C

5.1: 67 percent / Raney nickel; H₂ / methanol / 36 h / 22 °C / 18617.3 Torr

6.1: 78 percent / K₂CO₃ / dimethylformamide / 2.5 h

7.1: 84 percent / imidazole / dimethylformamide / 12 h / 22 °C

8.1: LDA / tetrahydrofuran; hexane / -107 - 22 °C

9.1: 52 percent / tetrahydrofuran / -106 - 22 °C

10.1: 86 percent / m-CPBA; diisopropylamine / CH₂Cl₂ / -77 - 22 °C

11.1: 85 percent / EtMgCl / tetrahydrofuran; diethyl ether; methanol / 0.83 h / -15 °C

12.1: 87 percent / NaH / dimethylformamide / 0 - 22 °C

13.1: Et₃N; trimethylsilyl triflate / CH₂Cl₂ / 0 - 22 °C

14.1: 0.561 g / BH₃*THF / tetrahydrofuran / 13.5 h / 22 °C

15.1: 50 percent / imidazole

16.1: PPh₃; Et₃N / Pd(OAc)2 / acetonitrile / 100 °C

With 1H-imidazole; n-butyllithium; borane-THF; trimethylsilyl trifluoromethanesulfonate; hydrogen; ethylmagnesium chloride; bis-(1,2-dimethylpropyl)borane; nickel; sodium hydride; potassium carbonate; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diisopropyl amide; palladium diacetate; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.2: Michael addition / 16.1: Heck reaction;
DOI:10.1002/adsc.200600301