(1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate

Base Information

Chemical Name:(1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate
CAS No.:250689-42-0
Molecular Formula:C₁₆H₁₉NO₅S
Molecular Weight:337.397
Hs Code.:

Synonyms:(1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate

Chemical Property:

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Technology Process of (1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate

There total 19 articles about (1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate 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%

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 252289-51-3
(1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propan-1-ol

: 250689-42-0
(1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate

Guidance literature:: With pyridine; dmap; at 0 ℃; for 3h;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T

Reference yield:

: 13834-07-6
(1R,3R,4S,8R)-9-hydroxy-p-menthol

: 250689-42-0
(1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate

Guidance literature:: Multi-step reaction with 13 steps

1: 91 percent / 1H-imidazole / dimethylformamide / 15 h / 0 - 20 °C

2: 62 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -79 °C

3: 100 percent / BuLi; (i-Pr)2NH / hexane; tetrahydrofuran / 1 h / -78 °C

4: N-bromosuccinimide / tetrahydrofuran / 2 h / 0 °C

5: 74 percent / 2,4,6-trimethyl-pyridine / 1 h / 145 - 150 °C

6: 55 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / 0 - 20 °C

7: 99 percent / VO(acac)2; t-BuOOH / benzene; CH₂Cl₂ / 2 h / 0 - 5 °C

8: 100 percent / Et₃N / tetrahydrofuran / 24 h / 0 - 20 °C

9: 95 percent / LiNEt₂ / tetrahydrofuran / 2 h / Heating

10: 98 percent / pyridine / benzene / 2 h / -5 - 20 °C

11: 40 percent / P(OMe)3; maleinic anhydride / benzene / 24 h / Heating

12: 89 percent / Bu₄NF*3H₂O / tetrahydrofuran / 14 h / 0 - 20 °C

13: 70 percent / pyridine; DMAP / 3 h / 0 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cerium(III) chloride; oxalyl dichloride; bis(acetylacetonate)oxovanadium; lithium diethylamide; tetrabutyl ammonium fluoride; maleic anhydride; dimethyl sulfoxide; triethylamine; diisopropylamine; phosphorous acid trimethyl ester; In tetrahydrofuran; 2,4,6-trimethyl-pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Substitution / 2: Oxidation / 3: Etherification / 4: Bromination / 5: Dehydrobromination / 6: Reduction / 7: Epoxidation / 8: Substitution / 9: Rearrangement / 10: Acylation / 11: Elimination / 12: Hydrolysis / 13: Acylation;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T

Reference yield:

: 7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2
isopulegol

: 250689-42-0
(1'R,2R)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate

Guidance literature:: Multi-step reaction with 14 steps

1.1: B₂H₆ / tetrahydrofuran / 2 h / 0 - 20 °C

1.2: NaOH; H₂O₂ / 0.5 h / Heating

2.1: 91 percent / 1H-imidazole / dimethylformamide / 15 h / 0 - 20 °C

3.1: 62 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -79 °C

4.1: 100 percent / BuLi; (i-Pr)2NH / hexane; tetrahydrofuran / 1 h / -78 °C

5.1: N-bromosuccinimide / tetrahydrofuran / 2 h / 0 °C

6.1: 74 percent / 2,4,6-trimethyl-pyridine / 1 h / 145 - 150 °C

7.1: 55 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / 0 - 20 °C

8.1: 99 percent / VO(acac)2; t-BuOOH / benzene; CH₂Cl₂ / 2 h / 0 - 5 °C

9.1: 100 percent / Et₃N / tetrahydrofuran / 24 h / 0 - 20 °C

10.1: 95 percent / LiNEt₂ / tetrahydrofuran / 2 h / Heating

11.1: 98 percent / pyridine / benzene / 2 h / -5 - 20 °C

12.1: 40 percent / P(OMe)3; maleinic anhydride / benzene / 24 h / Heating

13.1: 89 percent / Bu₄NF*3H₂O / tetrahydrofuran / 14 h / 0 - 20 °C

14.1: 70 percent / pyridine; DMAP / 3 h / 0 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cerium(III) chloride; oxalyl dichloride; bis(acetylacetonate)oxovanadium; lithium diethylamide; tetrabutyl ammonium fluoride; maleic anhydride; dimethyl sulfoxide; triethylamine; diisopropylamine; diborane; phosphorous acid trimethyl ester; In tetrahydrofuran; 2,4,6-trimethyl-pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: hydroboration / 1.2: Oxidation / 2.1: Substitution / 3.1: Oxidation / 4.1: Etherification / 5.1: Bromination / 6.1: Dehydrobromination / 7.1: Reduction / 8.1: Epoxidation / 9.1: Substitution / 10.1: Rearrangement / 11.1: Acylation / 12.1: Elimination / 13.1: Hydrolysis / 14.1: Acylation;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T