(1R,4S,5R)-1-isopropyl-4-[[(2-nitrobenzene)selenenyl]methyl]bicyclo[3.1.0]hexane

Base Information

Chemical Name:(1R,4S,5R)-1-isopropyl-4-[[(2-nitrobenzene)selenenyl]methyl]bicyclo[3.1.0]hexane
CAS No.:196941-66-9
Molecular Formula:C₁₆H₂₁NO₂Se
Molecular Weight:338.308
Hs Code.:

Synonyms:(1R,4S,5R)-1-isopropyl-4-[[(2-nitrobenzene)selenenyl]methyl]bicyclo[3.1.0]hexane

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Chemical Property of (1R,4S,5R)-1-isopropyl-4-[[(2-nitrobenzene)selenenyl]methyl]bicyclo[3.1.0]hexane

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Technology Process of (1R,4S,5R)-1-isopropyl-4-[[(2-nitrobenzene)selenenyl]methyl]bicyclo[3.1.0]hexane

There total 13 articles about (1R,4S,5R)-1-isopropyl-4-[[(2-nitrobenzene)selenenyl]methyl]bicyclo[3.1.0]hexane 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:

: 51694-22-5
ortho-nitrophenyl selenocyanate

: 20126-27-6
(1R,4S,5R)-1-isopropylbicyclo[3.1.0]hexane-4-methanol

: 196941-66-9
(1R,4S,5R)-1-isopropyl-4-[[(2-nitrobenzene)selenenyl]methyl]bicyclo[3.1.0]hexane

Guidance literature:: With tributylphosphine; In tetrahydrofuran; at 20 ℃; for 2.3h;
DOI:10.1021/ja9716160

Reference yield:

: (S)-2-Vinyl-pent-4-en-1-ol

: 196941-66-9
(1R,4S,5R)-1-isopropyl-4-[[(2-nitrobenzene)selenenyl]methyl]bicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 12 steps

1.1: imidazole

2.1: 9-BBN

2.2: H₂O₂

3.1: DMSO; SO₃*py; NEt₃

4.1: PPh₃

5.1: 100 percent / BuLi

6.1: 78 percent / Ti(O-i-Pr)3Cl; i-PrMgCl / diethyl ether / 3.25 h / -78 - 0 °C

7.1: diisopropylamine; BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: 213 mg / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

8.1: 180 mg / Dibal-H / hexane; diethyl ether / 0.5 h / -78 - 0 °C

9.1: (dimethylamino)pyridine; pyridine / 5 °C

10.1: 140 mg / LiBHEt₃ / tetrahydrofuran / 5 h / 20 °C

11.1: 80 mg / TBAF / tetrahydrofuran / 3.5 h / 20 °C

12.1: PBu₃ / tetrahydrofuran / 2.3 h / 20 °C

With pyridine; 1H-imidazole; triisopropoxytitanium(IV) chloride; dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; pyridine-SO₃ complex; tributylphosphine; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; diisobutylaluminium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; 1.1: silylation / 2.1: Addition / 2.2: Oxidation / 3.1: Oxidation / 4.1: Wittig reaction / 5.1: Dehydrobromination / 5.2: Acylation / 6.1: Cyclization / 7.1: Metallation / 7.2: Methylation / 8.1: Reduction / 9.1: Tosylation / 10.1: Reduction / 11.1: desilylation / 12.1: Condensation;
DOI:10.1021/ja9716160

Reference yield:

: 196941-56-7
(S)-tert-butyldimethyl((2-vinylpent-4-en-1-yl)oxy)silane

: 196941-66-9
(1R,4S,5R)-1-isopropyl-4-[[(2-nitrobenzene)selenenyl]methyl]bicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 11 steps

1.1: 9-BBN

1.2: H₂O₂

2.1: DMSO; SO₃*py; NEt₃

3.1: PPh₃

4.1: 100 percent / BuLi

5.1: 78 percent / Ti(O-i-Pr)3Cl; i-PrMgCl / diethyl ether / 3.25 h / -78 - 0 °C

6.1: diisopropylamine; BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

6.2: 213 mg / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

7.1: 180 mg / Dibal-H / hexane; diethyl ether / 0.5 h / -78 - 0 °C

8.1: (dimethylamino)pyridine; pyridine / 5 °C

9.1: 140 mg / LiBHEt₃ / tetrahydrofuran / 5 h / 20 °C

10.1: 80 mg / TBAF / tetrahydrofuran / 3.5 h / 20 °C

11.1: PBu₃ / tetrahydrofuran / 2.3 h / 20 °C

With pyridine; triisopropoxytitanium(IV) chloride; dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; pyridine-SO₃ complex; tributylphosphine; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; diisobutylaluminium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; 1.1: Addition / 1.2: Oxidation / 2.1: Oxidation / 3.1: Wittig reaction / 4.1: Dehydrobromination / 4.2: Acylation / 5.1: Cyclization / 6.1: Metallation / 6.2: Methylation / 7.1: Reduction / 8.1: Tosylation / 9.1: Reduction / 10.1: desilylation / 11.1: Condensation;
DOI:10.1021/ja9716160