methyl (2Z)-3-[4-(acetyloxy)-2,6-dimethylphenyl]-2-acetamidoprop-2-enoate

Base Information

• Chemical Name: methyl (2Z)-3-[4-(acetyloxy)-2,6-dimethylphenyl]-2-acetamidoprop-2-enoate
• CAS No.: 145235-85-4
• Molecular Formula: C16H19NO5
• Molecular Weight: 305.331
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID301139798
• Nikkaji Number: J3.043.115D,J500.691K
• Mol file: 145235-85-4.mol

Synonyms:145235-85-4;methyl (2Z)-3-[4-(acetyloxy)-2,6-dimethylphenyl]-2-acetamidoprop-2-enoate;(Z)-methyl 2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)acrylate;Methyl (Z)-2-acetaMido-3-(4-acetoxy-2,6-diMethylphenyl)-2-propenoate;methyl (Z)-2-acetamido-3-(4-acetyloxy-2,6-dimethylphenyl)prop-2-enoate;DTXSID301139798;CS-M3205;VFA23585;MFCD22418820;AKOS022168298;MH-0715;C12901;(Z)-methyl2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)acrylate;Methyl (2Z)-2-(acetylamino)-3-[4-(acetyloxy)-2,6-dimethylphenyl]-2-propenoate

Chemical Property of methyl (2Z)-3-[4-(acetyloxy)-2,6-dimethylphenyl]-2-acetamidoprop-2-enoate

Chemical Property:

• Boiling Point: 495.6±45.0 °C(Predicted)
• PKA: 12.52±0.46(Predicted)
• PSA: 81.70000
• Density: 1.177±0.06 g/cm3(Predicted)
• LogP: 2.26960
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 305.12632271
• Heavy Atom Count: 22
• Complexity: 459

Purity/Quality:

99% ^*data from raw suppliers

methyl(2Z)-3-[4-(acetyloxy)-2,6-dimethylphenyl]-2-acetamidoprop-2-enoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1C=C(C(=O)OC)NC(=O)C)C)OC(=O)C
• Isomeric SMILES: CC1=CC(=CC(=C1/C=C(/C(=O)OC)\NC(=O)C)C)OC(=O)C

Technology Process of methyl (2Z)-3-[4-(acetyloxy)-2,6-dimethylphenyl]-2-acetamidoprop-2-enoate

There total 4 articles about methyl (2Z)-3-[4-(acetyloxy)-2,6-dimethylphenyl]-2-acetamidoprop-2-enoate 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: 85.0%

Methyl 2-acetamidoacrylate (35356-70-8) + 4-iodo-3,5-dimethylphenyl acetate (145235-84-3) → methyl (Z)-2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)-2-propenoate (145235-85-4)

Guidance literature:

With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine; In acetonitrile; for 22h; Heating;

DOI:10.1055/s-1992-26212

Reference yield:

4-iodo-3,5-dimethylphenol (80826-86-4) → methyl (Z)-2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)-2-propenoate (145235-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / 0.5 h / 50 °C

2: 85 percent / Et₃N / Pd(OAc)2, tri-o-tolylphosphine / acetonitrile / 22 h / Heating

With pyridine; triethylamine; palladium diacetate; tris-(o-tolyl)phosphine; In acetonitrile;

DOI:10.1055/s-1992-26212

Reference yield:

2-acetylamino-3-methoxy-3-oxo-propyl acetate (55299-57-5) → methyl (Z)-2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)-2-propenoate (145235-85-4)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; at 73 ℃; for 13h; Large scale reaction;

DOI:10.1021/op200065p

upstream raw materials:

Methyl 2-acetamidoacrylate

4-iodo-3,5-dimethylphenyl acetate

4-iodo-3,5-dimethylphenol

2-acetylamino-3-methoxy-3-oxo-propyl acetate

Downstream raw materials:

(S)-N-acetyl-2,6-dimethyltyrosine

(S)-N-Boc-2,6-dimethyltyrosine

H-Dmt

(S)-4-acetoxy-N-acetyl-2,6-dimethylphenylalanine methyl ester