methyl 8-{[(2,4-dinitro-benzenesulfonyl)-(3-phenyl-propyl)-amino]methyl}-7,8-dihydro-3H-6,9-dioxa-3-aza-cyclopenta[a]naphthalene-2-carboxylate

Base Information

• Chemical Name: methyl 8-{[(2,4-dinitro-benzenesulfonyl)-(3-phenyl-propyl)-amino]methyl}-7,8-dihydro-3H-6,9-dioxa-3-aza-cyclopenta[a]naphthalene-2-carboxylate
• CAS No.: 704909-82-0
• Molecular Formula: C₂₈H₂₆N₄O₁₀S
• Molecular Weight: 610.601
• Mol file: 704909-82-0.mol

Synonyms:methyl 8-{[(2,4-dinitro-benzenesulfonyl)-(3-phenyl-propyl)-amino]methyl}-7,8-dihydro-3H-6,9-dioxa-3-aza-cyclopenta[a]naphthalene-2-carboxylate

Chemical Property of methyl 8-{[(2,4-dinitro-benzenesulfonyl)-(3-phenyl-propyl)-amino]methyl}-7,8-dihydro-3H-6,9-dioxa-3-aza-cyclopenta[a]naphthalene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 8-{[(2,4-dinitro-benzenesulfonyl)-(3-phenyl-propyl)-amino]methyl}-7,8-dihydro-3H-6,9-dioxa-3-aza-cyclopenta[a]naphthalene-2-carboxylate

There total 13 articles about methyl 8-{[(2,4-dinitro-benzenesulfonyl)-(3-phenyl-propyl)-amino]methyl}-7,8-dihydro-3H-6,9-dioxa-3-aza-cyclopenta[a]naphthalene-2-carboxylate 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: 92.0%

methyl (S)-2,3-dihydro-2-(hydroxymethyl)-7H-1,4-dioxino[2,3-e]-indole-8-carboxylate + 2,4-dinitro-N-(3-phenyl-propyl)-benzenesulfonamide (704909-83-1) → methyl 8-{[(2,4-dinitro-benzenesulfonyl)-(3-phenyl-propyl)-amino]methyl}-7,8-dihydro-3H-6,9-dioxa-3-aza-cyclopenta[a]naphthalene-2-carboxylate (704909-82-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jo035819k

Reference yield:

2,6-dibromophenol (608-33-3) → methyl 8-{[(2,4-dinitro-benzenesulfonyl)-(3-phenyl-propyl)-amino]methyl}-7,8-dihydro-3H-6,9-dioxa-3-aza-cyclopenta[a]naphthalene-2-carboxylate (704909-82-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 92 percent / N-iodosuccinimide / acetonitrile / 4 h / 20 °C

2.1: 96 percent / K₂CO₃ / acetone / 3 h / 65 °C

3.1: 74 percent / CuI; Cs₂CO₃ / dimethylformamide / 80 °C

4.1: HCl / H₂O; methanol / 6 h / 65 °C

4.2: 70 percent / methanesulfonic acid; P₂O₅ / CH₂Cl₂ / 24 h / 45 °C

5.1: 85 percent / NaBH₄; rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; N,N,N',N'-tetramethylethylenediamine / Pd(OAc)2 / tetrahydrofuran / 20 °C

6.1: 69 percent / BBr₃ / CH₂Cl₂ / 12 h / 20 °C

7.1: 73 percent / Co-salen oligomer / acetonitrile / 22 h / 20 °C

8.1: 76 percent / 2-(N,N-dimethylamino)-2'-di-tert-butylphosphinobiphenyl; Cs₂CO₃; Pd(OAc)2 / toluene / 40 h / 70 °C

9.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

10.1: 92 percent / PPh₃; DEAD / tetrahydrofuran / 1 h / 20 °C

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; N-iodo-succinimide; copper(l) iodide; salcomine; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; boron tribromide; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; diethylazodicarboxylate; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 7.1: Jacobsen's phenolic kinetic resolution;

DOI:10.1021/jo035819k

Reference yield:

2,6-dibromo-4-iodophenol (187407-15-4) → methyl 8-{[(2,4-dinitro-benzenesulfonyl)-(3-phenyl-propyl)-amino]methyl}-7,8-dihydro-3H-6,9-dioxa-3-aza-cyclopenta[a]naphthalene-2-carboxylate (704909-82-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 96 percent / K₂CO₃ / acetone / 3 h / 65 °C

2.1: 74 percent / CuI; Cs₂CO₃ / dimethylformamide / 80 °C

3.1: HCl / H₂O; methanol / 6 h / 65 °C

3.2: 70 percent / methanesulfonic acid; P₂O₅ / CH₂Cl₂ / 24 h / 45 °C

4.1: 85 percent / NaBH₄; rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; N,N,N',N'-tetramethylethylenediamine / Pd(OAc)2 / tetrahydrofuran / 20 °C

5.1: 69 percent / BBr₃ / CH₂Cl₂ / 12 h / 20 °C

6.1: 73 percent / Co-salen oligomer / acetonitrile / 22 h / 20 °C

7.1: 76 percent / 2-(N,N-dimethylamino)-2'-di-tert-butylphosphinobiphenyl; Cs₂CO₃; Pd(OAc)2 / toluene / 40 h / 70 °C

8.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

9.1: 92 percent / PPh₃; DEAD / tetrahydrofuran / 1 h / 20 °C

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; copper(l) iodide; salcomine; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; boron tribromide; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; diethylazodicarboxylate; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 6.1: Jacobsen's phenolic kinetic resolution;

DOI:10.1021/jo035819k

upstream raw materials:

2,4-dinitro-N-(3-phenyl-propyl)-benzenesulfonamide

2,6-dibromophenol

2,4-dinitrobenzenesulfonyl chloride

3-Phenylpropan-1-amine