(Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine

Base Information

• Chemical Name: (Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine
• CAS No.: 1108621-37-9
• Molecular Formula: C₂₈H₃₉NO₅
• Molecular Weight: 469.621
• Mol file: 1108621-37-9.mol

Synonyms:(Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine

Chemical Property of (Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine

There total 10 articles about (Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine 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: 87.0%

(Z)-2-[-2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxyethanamine (1108621-35-7) + 3-Chloro-2-methylpropene (563-47-3) → (Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine (1108621-37-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide; for 2h; Reflux;

DOI:10.1021/jo4023149

Reference yield:

2-(2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl)ethoxime (1108621-60-8) → (Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine (1108621-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium cyanoborohydride / methanol / 1 h / 20 °C / pH Ca_. 3

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / Reflux

With sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo4023149

Reference yield:

4-isopropoxy-2-bromo-5-methoxybenzaldehyde (56517-33-0) → (Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine (1108621-37-9)

Guidance literature:

Multi-step reaction with 6 steps

1: trans-bis(triphenylphosphine)palladium dichloride; copper(l) iodide; triethylamine / 24 h / 20 °C

2: acetic acid / 4 h / 100 °C

3: tin(ll) chloride / ethyl acetate / 10 h / 20 °C

4: hydrogen / ethyl acetate / 5 h / 760.05 Torr

5: sodium cyanoborohydride / methanol / 1 h / 20 °C / pH Ca_. 3

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / Reflux

With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; hydrogen; sodium cyanoborohydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tin(ll) chloride; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling;

DOI:10.1021/jo4023149

upstream raw materials:

(Z)-2-[-2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxyethanamine

3-Chloro-2-methylpropene

2-(2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl)ethoxime

4-isopropyloxy-3-methoxybenzaldehyde

Downstream raw materials:

1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline-N-(2-methylallyloxide)

(E)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine

N-benzoyl-norreticuline

1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline