Technology Process of (1aR*,6S*,7aR*,7bS*)-1a,2,3,4,6,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-6-(o-nitrophenylselenyl)-1H-cyclopropazulene
There total 16 articles about (1aR*,6S*,7aR*,7bS*)-1a,2,3,4,6,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-6-(o-nitrophenylselenyl)-1H-cyclopropazulene 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:
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107770-64-9,107869-96-5
(1aR*,6R*,7aR*,7bS*)-1a,2,3,4,6,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-1H-cyclopropazulen-6-ol
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107770-65-0
(1aR*,6S*,7aR*,7bS*)-1a,2,3,4,6,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-6-(o-nitrophenylselenyl)-1H-cyclopropazulene
- Guidance literature:
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With
tributylphosphine;
In
tetrahydrofuran;
at 0 ℃;
for 5.3h;
DOI:10.1021/ja00244a026
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107770-65-0
(1aR*,6S*,7aR*,7bS*)-1a,2,3,4,6,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-6-(o-nitrophenylselenyl)-1H-cyclopropazulene
- Guidance literature:
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Multi-step reaction with 13 steps
1: 82.5 percent / p-toluenesulfonic acid / benzene / 48 h / Heating
2: 92 percent / ethylzinc iodide / diethyl ether / 25 h / Heating
3: 100 percent / 1 N sulfuric acid / acetone / 8 h / Ambient temperature
4: 85 percent / 50percent NaH, KH / tetrahydrofuran / 15 h / Heating
5: 94 percent / NaBH4 / ethanol / 0.25 h / 0 °C
6: 92 percent / Et3N / DMAP / CH2Cl2 / 48 h / Heating
7: 89 percent / DBU / benzene / 72 h / Heating
8: 94 percent / KOH / aq. ethanol / 6 h / Heating
9: 71 percent / diethyl ether / 1.) -78 deg C, 15 min, 2.) 0 deg C, 3 h
10: NaBH4, CeCl3 / methanol / 2 h
12: 85 percent / (i-Bu)2AlH / CH2Cl2; hexane / 0.5 h / -78 °C
13: 55 percent / (n-Bu)3P / tetrahydrofuran / 5.3 h / 0 °C
With
potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; tributylphosphine; sulfuric acid; potassium hydride; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; ethylzinc iodide;
dmap; toluene-4-sulfonic acid;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; acetone; benzene;
DOI:10.1021/ja00244a026
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107770-65-0
(1aR*,6S*,7aR*,7bS*)-1a,2,3,4,6,7,7a,7b-octahydro-3,3,5,7b-tetramethyl-6-(o-nitrophenylselenyl)-1H-cyclopropazulene
- Guidance literature:
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Multi-step reaction with 11 steps
1: 100 percent / 1 N sulfuric acid / acetone / 8 h / Ambient temperature
2: 85 percent / 50percent NaH, KH / tetrahydrofuran / 15 h / Heating
3: 94 percent / NaBH4 / ethanol / 0.25 h / 0 °C
4: 92 percent / Et3N / DMAP / CH2Cl2 / 48 h / Heating
5: 89 percent / DBU / benzene / 72 h / Heating
6: 94 percent / KOH / aq. ethanol / 6 h / Heating
7: 71 percent / diethyl ether / 1.) -78 deg C, 15 min, 2.) 0 deg C, 3 h
8: NaBH4, CeCl3 / methanol / 2 h
10: 85 percent / (i-Bu)2AlH / CH2Cl2; hexane / 0.5 h / -78 °C
11: 55 percent / (n-Bu)3P / tetrahydrofuran / 5.3 h / 0 °C
With
potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; tributylphosphine; sulfuric acid; potassium hydride; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
dmap;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; acetone; benzene;
DOI:10.1021/ja00244a026
