(E)-6-(2-Amino-3-cyano-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

Base Information

Chemical Name:(E)-6-(2-Amino-3-cyano-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester
CAS No.:182011-48-9
Molecular Formula:C₁₈H₂₄N₂O₃
Molecular Weight:316.4
Hs Code.:

Synonyms:(E)-6-(2-Amino-3-cyano-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-6-(2-Amino-3-cyano-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

Chemical Property:

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Technology Process of (E)-6-(2-Amino-3-cyano-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

There total 11 articles about (E)-6-(2-Amino-3-cyano-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester 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: 42.0%

: 151-50-8
potassium cyanide

: 182011-47-8
(E)-6-(2-Amino-3-bromo-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

: 182011-48-9
(E)-6-(2-Amino-3-cyano-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 100 ℃; for 18h;
DOI:10.1021/jm9603633

Reference yield:

: 2416-94-6
2,3,6-trimethylphenol

: 182011-48-9
(E)-6-(2-Amino-3-cyano-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 84 percent / tetrabutylammonium tribromide / CH₂Cl₂; methanol / 0.17 h

2: DMAP / CH₂Cl₂ / 3 h

3: 1.) trifluoroacetic acid, 90percent HNO₃, 2.) NH₄OH / 1.) a) 0 deg C, 1 h, b) from 0 deg C, 20 deg C, 1 h, 2.) MeOH, 30 min

4: K₂CO₃ / dimethylformamide

5: H₂, NaOAc / 5percent Pd/C / ethanol

6: tetrahydrofuran / 24 h

7: 1.) t-BuLi / 1.) THF, pentane, from -78 deg C to -20 deg C, 2.) THF, pentane, -78 deg C, 5 min

8: pivalic acid / Heating

9: p-TsOH*H₂O / methanol / 12 h / 50 °C

10: NBS / dimethylformamide / 0.25 h / 0 °C

11: 42 percent / Pd(Ph₃P)4 / dioxane / 18 h / 100 °C

With dmap; ammonium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; tert.-butyl lithium; nitric acid; sodium acetate; tetra-N-butylammonium tribromide; potassium carbonate; toluene-4-sulfonic acid; trifluoroacetic acid; Trimethylacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm9603633

Reference yield:

: 51857-41-1
4-bromo-2,3,6-trimethylphenol

: 182011-48-9
(E)-6-(2-Amino-3-cyano-6-methoxy-4,5-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: DMAP / CH₂Cl₂ / 3 h

2: 1.) trifluoroacetic acid, 90percent HNO₃, 2.) NH₄OH / 1.) a) 0 deg C, 1 h, b) from 0 deg C, 20 deg C, 1 h, 2.) MeOH, 30 min

3: K₂CO₃ / dimethylformamide

4: H₂, NaOAc / 5percent Pd/C / ethanol

5: tetrahydrofuran / 24 h

6: 1.) t-BuLi / 1.) THF, pentane, from -78 deg C to -20 deg C, 2.) THF, pentane, -78 deg C, 5 min

7: pivalic acid / Heating

8: p-TsOH*H₂O / methanol / 12 h / 50 °C

9: NBS / dimethylformamide / 0.25 h / 0 °C

10: 42 percent / Pd(Ph₃P)4 / dioxane / 18 h / 100 °C

With dmap; ammonium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; tert.-butyl lithium; nitric acid; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; trifluoroacetic acid; Trimethylacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm9603633