(3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one

Base Information

Chemical Name:(3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one
CAS No.:222162-01-8
Molecular Formula:C₂₄H₃₃IN₂O₄Si
Molecular Weight:568.527
Hs Code.:

Synonyms:(3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one

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Chemical Property of (3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one

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Technology Process of (3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one

There total 14 articles about (3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one 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:

: 155206-86-3
(Z)-1-Bromo-4-[(tert-butyldimethylsilyl)oxy]-2-iodo-2-butene

: (3aR,7aS)-3a-(2-Nitro-phenyl)-1,2,3,3a,7,7a-hexahydro-indol-4-one

: 222162-01-8
(3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one

Guidance literature:: With potassium carbonate; lithium iodide; In acetonitrile; at 50 ℃; Yield given;
DOI:10.1002/(SICI)1521-3773(19990201)38:3<395::AID-ANIE395>3.0.CO;2-5

Reference yield:

: 609-73-4
o-nitroiodobenzene

: 222162-01-8
(3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one

Guidance literature:: Multi-step reaction with 10 steps

1: 72 percent / K₂CO₃ / dimethylsulfoxide / 85 - 90 °C

2: 85 percent / K₂CO₃ / acetone / Heating

3: 80 percent / toluene / 180 - 190 °C

4: 1.) O₃, 2.) NaBH₃CN / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, i-PrOH

5: 72 percent / 135 °C

6: HN(SiMe₃)2 / CH₂Cl₂; pentane / -20 °C

7: (PhSe)2 / tetrahydrofuran

8: 1.) O₃, 2.) i-Pr₂NH / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

9: methanol / Heating

10: K₂CO₃, LiI / acetonitrile / 50 °C

With diphenyl diselenide; sodium cyanoborohydride; potassium carbonate; ozone; diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium iodide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; acetonitrile; pentane;
DOI:10.1002/(SICI)1521-3773(19990201)38:3<395::AID-ANIE395>3.0.CO;2-5

Reference yield:

: 504-02-9
1,3-cylohexanedione

: 222162-01-8
(3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one

Guidance literature:: Multi-step reaction with 10 steps

1: 72 percent / K₂CO₃ / dimethylsulfoxide / 85 - 90 °C

2: 85 percent / K₂CO₃ / acetone / Heating

3: 80 percent / toluene / 180 - 190 °C

4: 1.) O₃, 2.) NaBH₃CN / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, i-PrOH

5: 72 percent / 135 °C

6: HN(SiMe₃)2 / CH₂Cl₂; pentane / -20 °C

7: (PhSe)2 / tetrahydrofuran

8: 1.) O₃, 2.) i-Pr₂NH / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

9: methanol / Heating

10: K₂CO₃, LiI / acetonitrile / 50 °C

With diphenyl diselenide; sodium cyanoborohydride; potassium carbonate; ozone; diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium iodide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; acetonitrile; pentane;
DOI:10.1002/(SICI)1521-3773(19990201)38:3<395::AID-ANIE395>3.0.CO;2-5