N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-3-<(2-nitrobenzyl)oxy>-10-oxo-5,6,7,8,9,10-hexahydrophenanthridine

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Chemical Name:N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-3-<(2-nitrobenzyl)oxy>-10-oxo-5,6,7,8,9,10-hexahydrophenanthridine
CAS No.:144019-94-3
Molecular Formula:C₃₃H₂₄N₂O₆
Molecular Weight:544.563
Hs Code.:

Synonyms:N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-3-<(2-nitrobenzyl)oxy>-10-oxo-5,6,7,8,9,10-hexahydrophenanthridine

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Chemical Property of N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-3-<(2-nitrobenzyl)oxy>-10-oxo-5,6,7,8,9,10-hexahydrophenanthridine

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Technology Process of N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-3-<(2-nitrobenzyl)oxy>-10-oxo-5,6,7,8,9,10-hexahydrophenanthridine

There total 18 articles about N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-3-<(2-nitrobenzyl)oxy>-10-oxo-5,6,7,8,9,10-hexahydrophenanthridine 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:

: 4746-93-4
1,4-dioxaspiro[4.5]decane-6-carboxylic acid

: 144019-94-3
N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-3-<(2-nitrobenzyl)oxy>-10-oxo-5,6,7,8,9,10-hexahydrophenanthridine

Guidance literature:: Multi-step reaction with 15 steps

1: 96 percent / DCC, DMAP / CH₂Cl₂ / 14 h / Ambient temperature

2: 87 percent / tetrahydrofuran / 96 h / Heating

3: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

4: 1.) 37percent aq. HCl, 2.) DIBAL, LiAlH₄, 3.) silica gel, O₂

5: 88 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 25 °C

6: 80 percent / 14 h / 25 °C

7: 98 percent / K₂CO₃ / methanol / 2 h / 25 °C

8: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

9: 89 percent / H₂ / 10percent Pd/C / ethanol / 4 h / 760 Torr

10: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 10 min, 2.) THF, 25 deg C, 1 h

11: 98 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C

12: 1.) Pd(PPh₃)4, n-PrNH₂, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 5 h

13: m-CPBA / CH₂Cl₂ / 1 h / 25 °C

14: 82 percent / 48percent aq. HBr / tetrahydrofuran / 2 h / 25 °C

15: 1.) AgNO₃, 2.) KCN / 1.) THF, EtOH, H₂O, 25 deg C, 1 h, 2.) THF, EtOH, H₂O, 25 deg C, 10 min

With 2,6-dimethylpyridine; hydrogenchloride; propylamine; dmap; potassium cyanide; copper(l) iodide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; hydrogen; oxygen; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; silver nitrate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/ja00049a023

Reference yield:

: 13747-72-3
ethyl 1,4-dioxa-spiro[4,5]decane-6-carboxylate

: 144019-94-3
N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-3-<(2-nitrobenzyl)oxy>-10-oxo-5,6,7,8,9,10-hexahydrophenanthridine

Guidance literature:: Multi-step reaction with 16 steps

1: aq. NaOH / methanol / 15 h / Heating

2: 96 percent / DCC, DMAP / CH₂Cl₂ / 14 h / Ambient temperature

3: 87 percent / tetrahydrofuran / 96 h / Heating

4: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

5: 1.) 37percent aq. HCl, 2.) DIBAL, LiAlH₄, 3.) silica gel, O₂

6: 88 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 25 °C

7: 80 percent / 14 h / 25 °C

8: 98 percent / K₂CO₃ / methanol / 2 h / 25 °C

9: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

10: 89 percent / H₂ / 10percent Pd/C / ethanol / 4 h / 760 Torr

11: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 10 min, 2.) THF, 25 deg C, 1 h

12: 98 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C

13: 1.) Pd(PPh₃)4, n-PrNH₂, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 5 h

14: m-CPBA / CH₂Cl₂ / 1 h / 25 °C

15: 82 percent / 48percent aq. HBr / tetrahydrofuran / 2 h / 25 °C

16: 1.) AgNO₃, 2.) KCN / 1.) THF, EtOH, H₂O, 25 deg C, 1 h, 2.) THF, EtOH, H₂O, 25 deg C, 10 min

With 2,6-dimethylpyridine; hydrogenchloride; propylamine; dmap; potassium cyanide; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; hydrogen; oxygen; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; silver nitrate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/ja00049a023

Reference yield:

: 144019-65-8
3-(benzyloxy)-7,8,9,10-tetrahydrophenanthridine

: 144019-94-3
N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-3-<(2-nitrobenzyl)oxy>-10-oxo-5,6,7,8,9,10-hexahydrophenanthridine

Guidance literature:: Multi-step reaction with 11 steps

1: 88 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 25 °C

2: 80 percent / 14 h / 25 °C

3: 98 percent / K₂CO₃ / methanol / 2 h / 25 °C

4: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

5: 89 percent / H₂ / 10percent Pd/C / ethanol / 4 h / 760 Torr

6: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 10 min, 2.) THF, 25 deg C, 1 h

7: 98 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C

8: 1.) Pd(PPh₃)4, n-PrNH₂, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 5 h

9: m-CPBA / CH₂Cl₂ / 1 h / 25 °C

10: 82 percent / 48percent aq. HBr / tetrahydrofuran / 2 h / 25 °C

11: 1.) AgNO₃, 2.) KCN / 1.) THF, EtOH, H₂O, 25 deg C, 1 h, 2.) THF, EtOH, H₂O, 25 deg C, 10 min

With 2,6-dimethylpyridine; propylamine; potassium cyanide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; silver nitrate; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/ja00049a023