Methyl (2E,3E,5E)-6-(4-chloro-3-methoxyphenyl)-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate

Base Information

• Chemical Name: Methyl (2E,3E,5E)-6-(4-chloro-3-methoxyphenyl)-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate
• CAS No.: 128862-28-2
• Molecular Formula: C₁₇H₁₉ClO₄
• Molecular Weight: 322.788
• DSSTox Substance ID: DTXSID401043590
• Mol file: 128862-28-2.mol

Synonyms:SCHEMBL9065999;DTXSID401043590;128862-28-2;Methyl (2E,3E,5E)-6-(4-chloro-3-methoxyphenyl)-2- (methoxymethylidene)-3-methylhexa-3,5-dienoate

Chemical Property of Methyl (2E,3E,5E)-6-(4-chloro-3-methoxyphenyl)-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate

Chemical Property:

• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 322.0971868
• Heavy Atom Count: 22
• Complexity: 454

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Methyl (2E,3E,5E)-6-(4-chloro-3-methoxyphenyl)-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate

There total 20 articles about Methyl (2E,3E,5E)-6-(4-chloro-3-methoxyphenyl)-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate 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: 25.0%

(3Z,5E)-6-(4-Chloro-3-methoxy-phenyl)-2-[1-hydroxy-meth-(E)-ylidene]-3-methyl-hexa-3,5-dienoic acid methyl ester (128862-51-1,128862-55-5) + dimethyl sulfate (77-78-1) → (9E)-Strobilurin B (128862-28-2) + (3Z,5E)-6-(4-Chloro-3-methoxy-phenyl)-2-[1-methoxy-meth-(E)-ylidene]-3-methyl-hexa-3,5-dienoic acid methyl ester (65105-52-4,128862-28-2) + methyl (2E,3Z,5E)-6-(4-chloro-3-methoxyphenyl)-2-methoxymethylidene-3-methylhexa-3,5-dienoate (65105-52-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0040-4039(01)80582-7

Reference yield: 25.0%

(3Z,5E)-6-(4-Chloro-3-methoxy-phenyl)-2-[1-hydroxy-meth-(E)-ylidene]-3-methyl-hexa-3,5-dienoic acid methyl ester (128862-51-1,128862-55-5) + dimethyl sulfate (77-78-1) → (9E)-Strobilurin B (128862-28-2) + (3Z,5E)-6-(4-Chloro-3-methoxy-phenyl)-2-[1-methoxy-meth-(E)-ylidene]-3-methyl-hexa-3,5-dienoic acid methyl ester (65105-52-4,128862-28-2) + methyl (2E,3Z,5E)-6-(4-chloro-3-methoxyphenyl)-2-methoxymethylidene-3-methylhexa-3,5-dienoate (65105-52-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0040-4039(01)80582-7

Reference yield:

2-chloro-5-methylphenol (615-74-7) → (9E)-Strobilurin B (128862-28-2)

Guidance literature:

Multi-step reaction with 10 steps

1: K₂CO₃ / dimethylformamide / Ambient temperature

2: 62 percent / NBS, AIBN / CCl₄ / Heating

3: 73 percent / toluene / Heating

4: t-BuOK / tetrahydrofuran / Ambient temperature

5: tetrahydrofuran / Ambient temperature

6: H₂O / pTSA / acetone / 50 °C

7: 80 percent / toluene / Heating

9: NaH / Ambient temperature

10: 27 percent / K₂CO₃ / dimethylformamide / Ambient temperature

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4039(01)80582-7

upstream raw materials:

(3Z,5E)-6-(4-Chloro-3-methoxy-phenyl)-2-[1-hydroxy-meth-(E)-ylidene]-3-methyl-hexa-3,5-dienoic acid methyl ester

dimethyl sulfate

2-chloro-5-methylphenol

2-chloro-5-methylanisole