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

Base Information

Chemical Name:N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-6a,10a-epoxy-2-<(2-nitrobenzyl)oxy>-10-oxo-5,6,6a,7,8,9,10,10a-octahydrophenanthridine
CAS No.:144154-91-6
Molecular Formula:C₃₃H₂₄N₂O₇
Molecular Weight:560.563
Hs Code.:

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

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

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

There total 12 articles about N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-6a,10a-epoxy-2-<(2-nitrobenzyl)oxy>-10-oxo-5,6,6a,7,8,9,10,10a-octahydrophenanthridine 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:

: 100713-03-9
2-hydroxy-7,8,9,10-tetrahydrophenanthridine

: 144154-91-6
N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-6a,10a-epoxy-2-<(2-nitrobenzyl)oxy>-10-oxo-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Guidance literature:: Multi-step reaction with 11 steps

1: 94 percent / potassium carbonate, tetra-n-butylammonium iodide / dimethylformamide / 3 h / 25 °C

2: 87 percent / m-CPBA / CH₂Cl₂ / 1 h / 25 °C

3: 74 percent / 1 h / 70 °C

4: 89 percent / Dowex 1*8-200 / methanol / 24 h / 60 °C

5: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

6: 1.) THF, from -78 deg C to 0 deg C, 2.) THF, from -78 deg C to 25 deg C, 1 h

7: 95 percent / m-CPBA / CH₂Cl₂ / 2 h / 25 °C

8: 88 percent / tert-butyl mercaptan, tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 0.5 h / 20 °C

9: 100 percent / pyridinium chlorochromate (PCC), molecular sieves 4A / CH₂Cl₂ / 3 h / 25 °C

10: 78 percent / copper(I) iodide, n-butylamine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / CH₂Cl₂ / 2 h / 25 °C

11: 1.) silver nitrate, 2.) potassium cyanide / 1.) H₂O, EtOH, THF, 25 deg C, 1 h, 2.) H₂O, EtOH, THF, 25 deg C, 30 min

With 2,6-dimethylpyridine; potassium cyanide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4 A molecular sieve; Dowex 1*8-200; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; silver nitrate; 2-methylpropan-2-thiol; N-butylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00049a022

Reference yield:

: 35417-86-8
2-methoxy-7,8,9,10-tetrahydro-phenanthridine

: 144154-91-6
N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-6a,10a-epoxy-2-<(2-nitrobenzyl)oxy>-10-oxo-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Guidance literature:: Multi-step reaction with 12 steps

1: sodium ethanethiolate / dimethylformamide / 4 h / 160 °C

2: 94 percent / potassium carbonate, tetra-n-butylammonium iodide / dimethylformamide / 3 h / 25 °C

3: 87 percent / m-CPBA / CH₂Cl₂ / 1 h / 25 °C

4: 74 percent / 1 h / 70 °C

5: 89 percent / Dowex 1*8-200 / methanol / 24 h / 60 °C

6: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

7: 1.) THF, from -78 deg C to 0 deg C, 2.) THF, from -78 deg C to 25 deg C, 1 h

8: 95 percent / m-CPBA / CH₂Cl₂ / 2 h / 25 °C

9: 88 percent / tert-butyl mercaptan, tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 0.5 h / 20 °C

10: 100 percent / pyridinium chlorochromate (PCC), molecular sieves 4A / CH₂Cl₂ / 3 h / 25 °C

11: 78 percent / copper(I) iodide, n-butylamine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / CH₂Cl₂ / 2 h / 25 °C

12: 1.) silver nitrate, 2.) potassium cyanide / 1.) H₂O, EtOH, THF, 25 deg C, 1 h, 2.) H₂O, EtOH, THF, 25 deg C, 30 min

With 2,6-dimethylpyridine; potassium cyanide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4 A molecular sieve; Dowex 1*8-200; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; silver nitrate; 2-methylpropan-2-thiol; N-butylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; sodium thioethylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00049a022

Reference yield:

: 144127-48-0
2-<(2-nitrobenzyl)oxy>-7,8,9,10-tetrahydrophenanthridine

: 144154-91-6
N-<(phenyloxy)carbonyl>-6-<3(Z)-hexene-1,5-diynyl>-6a,10a-epoxy-2-<(2-nitrobenzyl)oxy>-10-oxo-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent / m-CPBA / CH₂Cl₂ / 1 h / 25 °C

2: 74 percent / 1 h / 70 °C

3: 89 percent / Dowex 1*8-200 / methanol / 24 h / 60 °C

4: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

5: 1.) THF, from -78 deg C to 0 deg C, 2.) THF, from -78 deg C to 25 deg C, 1 h

6: 95 percent / m-CPBA / CH₂Cl₂ / 2 h / 25 °C

7: 88 percent / tert-butyl mercaptan, tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 0.5 h / 20 °C

8: 100 percent / pyridinium chlorochromate (PCC), molecular sieves 4A / CH₂Cl₂ / 3 h / 25 °C

9: 78 percent / copper(I) iodide, n-butylamine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / CH₂Cl₂ / 2 h / 25 °C

10: 1.) silver nitrate, 2.) potassium cyanide / 1.) H₂O, EtOH, THF, 25 deg C, 1 h, 2.) H₂O, EtOH, THF, 25 deg C, 30 min

With 2,6-dimethylpyridine; potassium cyanide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4 A molecular sieve; Dowex 1*8-200; tetrabutyl ammonium fluoride; silver nitrate; 2-methylpropan-2-thiol; N-butylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00049a022